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Chicago Illinois Vacation Rentals - Apartment
1 / 35

Chicago Apartment
4 Bedrooms / 2 Bathrooms / Sleeps 8
Apartment / 4 Bedrooms / Sleeps 8

from

$175

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$175 - $250
Per week:$1,100 - $1,500
Pets allowed:Yes
Internet:Yes

Large Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Large, Cozy Place Ideal For Value Seekers Looking For A Memorable And Culturally- diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites In Chicago. From...

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Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 6
Condo / 3 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$315

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:6
Type:Condo
Per night:$315
Per week:$2,205
Pets allowed:No
Internet:No

Professionally decorated, this air- conditioned, 3 bedroom condo can easily lodge up to 10 guests. All the 3 bedrooms include king- size bed. The bathroom is well appointed as per modern standards. If guests decide to prepare yummy meals at home , then they can enjoy cooking in...

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Stunning Views and Spacious

“ Excellent ”
December 19, 2012
We visited Chicago for a family function. The entire famiy was in awe of this beautifully decorated and spacious condo, that also ahd the most beautiful and trannquilizing view. After a day out in the city it was nice to come home to this beautiful property. I would highly recommend staying here, the staff was accomodating and friendly as well.
Nancy Roy, Florida, Tampa

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Chicago Illinois Vacation Rentals - Home
1 / 19

Chicago Home
3 Bedrooms / 2 Bathrooms / Sleeps 10
Home / 3 Bedrooms / Sleeps 10

from

$115

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:10
Type:Home
Per night:$115 - $215
Per week:$805 - $1,505
Pets allowed:Yes
Internet:Yes

The Space Modern 3BD 2Bth Brick- Style Ranch! Sleeps 10! ! ASK ABOUT OUR PRICE MATCHING OPTION! ! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. - 3 Bedrooms - 2 Bathroom - Hardwood Floors - Tiled Bathroom -...

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1 / 7

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$175

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$175
Per week:$1,225
Pets allowed:No
Internet:No

You will be sure to enjoy your stay in Chicago in this newly renovated, spacious, two bedroom and two bathroom oasis in the heart of Lincoln Park. Each unit is complete with dark, hardwood floors, brand new kitchen, and an open concept living space. Located at 2835 N. Clark Street,...

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1 / 6

Chicago Condo
4 Bedrooms / 2 Bathrooms / Sleeps 8
Condo / 4 Bedrooms / Sleeps 8

(2)“ Excellent ”2 Reviews

from

$300

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Condo
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:Yes

Brand new 4 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you’re planning a weekend excursion, business trip or need a comfortable place to stay for family or friends, consider our newly rehabbed Guesthouse on Roscoe St. Trendy Roscoe Village...

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Wedding weekend

“ Excellent ”
May 28, 2014
Our 3 generations stayed for a wedding weekend at both the red and brown line flats. This allowed for the baby to have quiet for sleep while the adults gathered in the other flat or deck. We were able to share many meals outside on the deck while our toddler was entertained by the brown line trains passing through. The beds were comfortable and the kitchen appliances were all great. The location in Wrigleyville was convenient to everything...bars , restaurants ,shops,and of course Wrigley Field. It was a bonus to have garage space to park. We would stay there again.
Steve Ellis, Kalamazoo,Mi USA

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Front Door To Biddle House
1 / 18

Chicago Guesthouse
4 Bedrooms / 2 Bathrooms / Sleeps 10
Guesthouse / 4 Bedrooms / Sleeps 10

(4)“ Excellent ”4 Reviews

from

$225

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:10
Type:Guesthouse
Per night:$225
Per week:$1,575
Pets allowed:Yes
Internet:Yes

Chicago Vacation Rental License #2120297, #2120298 There are two fully furnished apartments available at the Biddle House. These are available to rent together or separately. Each has two bedrooms, one bathroom, a fully equipped kitchen, dining room and living room. Continental...

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Kudos

“ Excellent ”
June 22, 2015
We thoroughly enjoyed our stay. I was comfortable hosting 7 cousins because I once live on St. Michael's Ct. Parking worked out very well, in spite of the Art Fair. Small kitchens were a challenge, but we managed. A few standard condiments would have been nice. We were 8 adults so beds were adequate and comfortable. Futon and fold-out chair were a plus. One thing we wished for was more towels. There were not enough bath towels for each of us to have our own. Also kitchen towels were minimal. The doorknob on the first floor bedroom off the dining room needs fixing. Overall, a lovely experience and we watched the Blackhawks win the cup!. I would not hesitate to rent this property again for a similar gathering.
Ruth Thomas, Elmhurst, IL

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1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4
Condo / 1 Bedroom / Sleeps 4

(6)“ Excellent ”6 Reviews

from

$105

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$105
Per week:$735
Pets allowed:No
Internet:No

Welcome to Chicago! Come visit our 1bd/1ba condo. This is a very large unit - - the largest floor plan downtown. Our condo is located in the heart of downtown Chicago. It is 1 block from the Navy Pier where there are shops, restaurants and the lakefront. We are a 5 min walk...

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Visiting my sister.

“ Excellent ”
May 24, 2014
The condo in the Optima building was fantastic and better than advertised. The condo was clean and efficient. The bathroom was nice and they had cable with premium channels. By far the best was the view. In the 15th floor you can see Navy Pier and the lake. The building had a nice gym on the 10th floor and a rooftop area with a jacuzzi. Excellent trip and excellent place.
Erik Scales, Concord, CA

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Chicago Illinois Vacation Rentals - Apartment
1 / 14

Chicago Apartment
2 Bedrooms / 1.5 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$275

/ night

Email Owner
Bedrooms:2
Bathrooms:1.5
Sleeps:6
Type:Apartment
Per night:$275
Per week:$1,925
Pets allowed:No
Internet:Yes

Located near the corner of Orchard St and Deming Place is this gorgeous historic two bedroom, 1. 5 bathroom apartment within a grand mansion. There are two bedrooms, a very large living room, a full kitchen and dining room. There is also a lovely yard that guests are welcome to...

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Chicago Illinois Vacation Rentals - Apartment
1 / 23

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:Yes
Internet:Yes

Our vintage apartment is located in the beautiful Chicago neighborhood of Lakeview with many ethnic restaurants and clubs with- in walking distance. Try a different ethnic specialty every night of the week. Stroll 2 blocks through the neighborhood to the elevated train to downtown...

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Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 10
Condo / 3 Bedrooms / Sleeps 10

from

$315

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:10
Type:Condo
Per night:$315
Per week:$2,205
Pets allowed:No
Internet:No

Professionally decorated, this air- conditioned, 3 bedroom condo can easily lodge up to 10 guests. All the 3 bedrooms include king- size bed. The bathroom is well appointed as per modern standards. If guests decide to prepare yummy meals at home , then they can enjoy cooking in...

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Steps To Navy Pier - Beaches, Shops, Restaurants, Night Life and More!
1 / 37

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 2 Bedrooms / Sleeps 6

(24)“ Excellent ”24 Reviews

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$200 - $250
Per week:$1,400 - $1,750
Pets allowed:No
Internet:Yes

LOCATION LOCATION LOCATION! CAN'T BEAT IT! Views Views Views! Breathtaking Lake and City Views! ! Looks Like Hawii Up There! Set in the heart of Downtown Chicago, our Chicago apt is ideally placed for visitors to experience all that the city has to offer. On the doorstep...

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Magnificent condo

“ Excellent ”
July 1, 2015
Met all of our expectations! Spectacular view of Chicago and excellent location for museums and all Chicago shopping. Condo was very clean with excellent amenities
Ray Duchscherer, Colleyville Texas. Usa

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1 / 17

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(2)“ Excellent ”2 Reviews

from

$149

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$149 - $279
Per week:$950 - $1,650
Pets allowed:No
Internet:Yes

Please call/e- mail for more information....

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great location

“ Excellent ”
November 13, 2012
It's super easy to get anywhere from here. You can catch a bus right outside the building or walk a couple of blocks to the "L" trains. We rode the train to/from the airport and had no trouble with our luggage for the short walk or on the train.Building personnel were friendly and helpful. Nice grocery store/market within easy walking distance. The price you pay for the convenient location is that the building is directly on Michigan Avenue, which is busy (loud) night and day, so bring earplugs or a white noise machine.The building is not new, but we were comfortable for our 5 night stay. Don't expect to make any gourmet meals in this kitchen, but the basics are provided. Ditto for sheets/towels. Rental management was quite accomodating when we needed to change our departure date only a week before our stay. They refunded the extra night with no hassle.We would stay here again.
Elizabeth Book, Mississippi, USA

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Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

(5)“ Excellent ”5 Reviews

from

$89

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$89 - $220
Per week:$600 - $1,200
Pets allowed:No
Internet:Yes

These Vacation Rentals are located in the Chicago LOOP, a mixed- use neighborhood west of Michigan Avenue that includes apartments, homes, businesses and retailers surrounded by magnificent parks that are framed by the Chicago River to the North, Buckingham Fountain to the South,...

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Family stayed for convention

“ Excellent ”
May 25, 2013
Would've gave a 5 star if it wasn't for the bad experience during check in. Front desk person didn't have any record of my reservation and there was no parking pass as well which I paid for. After some time all was sorted out and I enjoyed my stay. Perfect location close to transportation and also walking distance to many restaurants and activities. Room was spacious and clean. From now on this is the only way I will stay when I come to Chicago. Great for family that doesn't want to deal with hassle of limited resources at a hotel.
jake lance, Illinois

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1 / 11

Chicago Apartment
3 Bedrooms / 2.5 Bathrooms / Sleeps 8
Apartment / 3 Bedrooms / Sleeps 8

(40)“ Excellent ”40 Reviews

from

$250

/ night

Email Owner
Bedrooms:3
Bathrooms:2.5
Sleeps:8
Type:Apartment
Per night:$250 - $315
Per week:$1,750 - $2,205
Pets allowed:No
Internet:No

Walk to Everything Downtown! Enjoy Stunning Views of the City Skyline and Grant Park! ONE OF FEW 3BD/2. 5BA UNITS RIGHT IN THE MIDDLE OF DOWNTOWN CHICAGO. Very affordable! WALK TO EVERYTHING YES, THESE ARE THE VIEWS! BREATHTAKING VIEWS OF THE CITY SKYLINE AND ...

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Amazing Find

“ Excellent ”
May 20, 2015
This was such a great place to be. Very well kept and the location is amazing. There is absolutely nothing bad to say about our time there and I would recommend this location to anyone.
sheldon colen, Las Vegas, NV

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Bella's livingroom
1 / 8

Chicago Apartment
4 Bedrooms / 2 Bathrooms / Sleeps 8
Apartment / 4 Bedrooms / Sleeps 8

(11)“ Excellent ”11 Reviews

from

$150

/ night

Email Owner
Bedrooms:4
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$150
Per week:$1,000
Pets allowed:No
Internet:Yes

The Aster House consists of 3 private fully furnished apartments: 1. Alice's Annex is a 1. 5 bedroom/1 bath with a queen bed in the bedroom, a single bed in a sleeping nook, queen sleeper sofa to sleep up to 5 guests. 2. Elizabeth's Place is a 3 bedroom/1 bath with 1 queen...

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Aster House Apts.

“ Excellent ”
July 22, 2014
The Aster house is a beautiful old home with very accommodating charm and appeal. There were a few quirks that needed to be worked out, but the owner was accessible and quick to respond to our needs. The neighborhood was lovely and very nicely located to shops and restaurants and some evening entertainment. We loved staying in the Aster House and will hope to do so again... and again!!
Kathi Bennett, California

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1 / 8

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$110

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$110 - $149
Per week:$650 - $850
Pets allowed:No
Internet:Yes

Vintage Mansion on Kedzie Blvd - Vacation Rental License xxxxxx property. This apartment is located on the 3rd floor of a Historic Mansion, overlooking Kedzie Blvd. in the city of Chicago. The apartment is very spacious, approximately 1200 sq ft of space, large living...

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Chicago Illinois Vacation Rentals - Apartment
1 / 36

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

(1)“ Excellent ”1 Review

from

$90

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Apartment
Per night:$90 - $150
Per week:$540 - $900
Pets allowed:No
Internet:Yes

Comfy Rental In A Neighborhood That Has Kept Its Old World Charm With The New! Artsy, Quiet And Comfortable Place Ideal For Value Seekers Looking For A Memorable And Culturally- Diverse Experience In A Quaint Neighborhood That's Also A Convenient Base To Explore Other Fun Sites...

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Chicago family vacation

“ Excellent ”
June 16, 2015
My husband and I thoroughly enjoyed our stay at this property.The unit provided everything we needed and more. Virgilio wasalso thoughtful with providing a grocery cart so we could walk to the local store and put our purchases in the cart, thus avoiding our having to pay for bags. The unit was home away from home for us. The location was excellent and we look forward to booking the unit next year.
Irene Menchaca Booth, San Diego, CA, USA

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Chicago Illinois Vacation Rentals - Apartment
1 / 15

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2
Apartment / Studio / Sleeps 2

from

$99

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$99 - $149
Per week:$600 - $850
Pets allowed:No
Internet:Yes

Corporate furnished apartment in the heart of Millennium Park, walking distance to transportation, restaurants and the lake front. The apartment comes fully furnished, has equipped kitchen, flat screen TVs, basic cable, Internet and all utilities are included. Rates vary...

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Chicago Illinois Vacation Rentals - Apartment
1 / 23

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Beautiful large true 1 bedroom space with plenty of square footage and stunning furnishings. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor...

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Chicago Illinois Vacation Rentals - Studio
1 / 22

Chicago Studio
-1 Bedroom / 1 Bathroom / Sleeps 2
Studio / -1 Bedroom / Sleeps 2

Bedrooms:-1
Bathrooms:1
Sleeps:2
Type:Studio
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Beautiful open floorplan studio with wall to wall bamboo hardwood flooring, open kitchen with tile backsplash, stainless steel appliances, and granite countertops, huge walk- in closet, floor to ceiling windows exposing city views, updated large bathroom with stone surround,...

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Chicago Illinois Vacation Rentals - Studio
1 / 22

Chicago Studio
-1 Bedroom / 1 Bathroom / Sleeps 2
Studio / -1 Bedroom / Sleeps 2

Bedrooms:-1
Bathrooms:1
Sleeps:2
Type:Studio
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Amazing unit features wall to wall cherry hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows exposing great Chicago River and city skyline views, beautifully updated...

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Chicago Illinois Vacation Rentals - Apartment
1 / 37

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Huge beautiful 1 bedroom with loads of space and all furnishings you need. This unit features beautiful wall to wall hardwood floors and upgraded carpeting in bedroom, stunning updated kitchen with quartz countertops and espresso cabinetry, large marble bathrooms, floor to ceiling...

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Chicago Illinois Vacation Rentals - Studio
1 / 27

Chicago Studio
-1 Bedroom / 1 Bathroom / Sleeps 2
Studio / -1 Bedroom / Sleeps 2

Bedrooms:-1
Bathrooms:1
Sleeps:2
Type:Studio
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:No

White quartz countertops, two- tone cabinetry, Frigidaire stainless steel appliances, gas stoves and white glass mosaic tile backsplashFull size washer/dryerCustom designed wide plank flooring throughoutWalk in closetContemporary bath finishesEverything about the building has been...

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Chicago Illinois Vacation Rentals - Apartment
1 / 12

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 6
Apartment / 2 Bedrooms / Sleeps 6

from

$300

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:6
Type:Apartment
Per night:$300
Per week:$2,100
Pets allowed:No
Internet:Yes

This 1200 square foot, two bedroom, two bathroom unit is located within a Victorian four flat in the heart of Old Town, at Eugenie and Sedgwick Streets. There are two queen size beds, a lovely living room with a sleeper sofa and a newly renovated kitchen. Lit by plenty of natural...

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1 / 24

Chicago Townhouse
3 Bedrooms / 2 Bathrooms / Sleeps 8
Townhouse / 3 Bedrooms / Sleeps 8

from

$300

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Townhouse
Per night:$300 - $450
Per week:$2,100 - $3,150
Pets allowed:No
Internet:Yes

Gorgeous, Luxury Oak Park area Townhome…corner unit…completely furnished…. close proximity (2 min. ) to the historic Oak Park area…home of Frank Lloyd Wright and Ernest Hemingway! Beautiful landscaping, total 2, 000 sq. ft. , alarm system, central air. Stunning designer...

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Chicago Illinois Vacation Rentals - Apartment
1 / 4

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

A truly beautiful space that features a defined living area and bedroom space. Unit features wall to wall espresso hardwood floors, stunning kitchen with quartz countertops and snaidero cabinetry, loads of storage space with professionally organized closets, floor to ceiling windows...

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Chicago Illinois Vacation Rentals - Condo
1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4
Condo / 1 Bedroom / Sleeps 4

from

$195

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$195 - $340
Per week:$1,365 - $2,380
Pets allowed:No
Internet:Yes

Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand Chicago river front — an intimate haven on the magnificent mile — offering chic accommodations in an exceptional setting. Just outside your door is Chicago's premier shopping...

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1 / 7

Chicago Condo
3 Bedrooms / 2 Bathrooms / Sleeps 6
Condo / 3 Bedrooms / Sleeps 6

(4)“ Excellent ”4 Reviews

from

$400

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:6
Type:Condo
Per night:$400
Per week:$2,800
Pets allowed:No
Internet:Yes

Beautifully done high- end furnished 3 bedroom | 2 bath | located downtown Chicago...

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Amazing View and Location

“ Excellent ”
July 12, 2015
Our family of 5 stayed here for a long weekend in July. The view is about a 270 degree view. Amazing! The location was close to several parks, Navy Pier, Maggy Daily park rocks if you have kids 12 and under- a must! The owner and property manager were very responsive and helpful. They gave 1st class service. Highly recommend.
Kristina Fentress, Texas

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Chicago Illinois Vacation Rentals - Apartment
1 / 29

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 2
Apartment / 1 Bedroom / Sleeps 2

Bedrooms:1
Bathrooms:1
Sleeps:2
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

Beautifully updated studio unit features a large open layout with loads of closet space. Unit features wall to wall dark hardwood floors, updated upgraded kitchen with espresso cabinetry and beautiful granite countertops, large windows exposing beautiful skyline views, huge closet...

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1 / 9

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

(3)“ Excellent ”3 Reviews

from

$109

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:5
Type:Apartment
Per night:$109 - $155
Per week:$700 - $1,050
Pets allowed:No
Internet:Yes

This is a 2 bedroom, 2 bathrooms, vintage building that has been rehabbed. This Chicago vacation rental apartment is located on Kedzie Blvd in Chicago, near the blue line. The apartment has washer/dryer in unit, stainless steal appliance, granite counter tops,...

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Great Location and amenities!

“ Excellent ”
June 12, 2013
I traveled to Chicago for a long business trip and chose to stay in a condo instead of a hotel. One Superior was the perfect place and location. Everything was within walking distance, great views, 7th Floor access to gym, pool, library were awesome!
christine grossmith, Carlsbad, CA

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Chicago Illinois Vacation Rentals - Home
1 / 17

Chicago Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 24
Home / 4 Bedrooms / Sleeps 24

(7)“ Excellent ”7 Reviews

from

$500

/ night

Email Owner
Bedrooms:4
Bathrooms:3.5
Sleeps:24
Type:Home
Per night:$500 - $1,150
Per week:$4,000 - $5,200
Pets allowed:No
Internet:Yes

Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home. This home is 15 blocks from Wrigley Field, 5 blocks to the Kennedy Expressway, 6 blocks to the EL, 2 blocks to grocery stores, etc, etc. Everything you need is here! This...

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2015 Sedgwick

“ Excellent ”
April 28, 2015
beautiful and plenty of room for a large group. Plenty of linens and towels. Full kitchen with all the necessities.
Cindi Jackson Krol, Montgomery, IL

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Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$229

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$229
Per week:$1,603
Pets allowed:No
Internet:Yes

You’re in the heart of downtown Chicago, Illinois, surrounded by shopping and entertainment venues. Located on State Street between Ohio and Ontario Streets, we’re three blocks west of Michigan Avenue's Magnificent Mile, and convenient to the Loop, the financial district ...

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Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$230

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$230
Per week:$1,610
Pets allowed:No
Internet:No

Situated one block from the Red Line CTA and the famous Magnificent Mile, our all- suite hotel provides easy access to Chicago O'Hare Airport and Midway Airport. Start your day with our hot full breakfast then unwind with our complimentary evening social Monday through Thursday –...

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Chicago Illinois Vacation Rentals - Apartment
1 / 7

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$230

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$230
Per week:$1,610
Pets allowed:No
Internet:Yes

Inn of Chicago The Finest Among Hotels in Downtown Chicago Welcome to the Inn of Chicago Magnificent Mile, a famously historic hotel rich with gorgeous contemporary decor and all the modern amenities the Chicago traveler is looking for. Situated ideally in the heart of downtown...

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Chicago Illinois Vacation Rentals - Condo
1 / 24

Chicago Condo
4 Bedrooms / 4 Bathrooms / Sleeps 14
Condo / 4 Bedrooms / Sleeps 14

from

$695

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Condo
Per night:$695 - $1,295
Per week:$4,865 - $9,065
Pets allowed:No
Internet:No

This is a luxury property consistent of two units one above the other. Book one or both to accommodate the size of your group. A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property with the City of Chicago (Wrigleyville) license...

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Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$219

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$219
Per week:$1,533
Pets allowed:No
Internet:Yes

Wyndham Grand Chicago River With sweeping views of the city skyline and Chicago River and plush oversized studio, the Wyndham Grand Chicago Riverfront provides the ideal home base for exploring our great city. This accommodation is outfitted with the latest modern amenities like...

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1 / 5

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 5
Apartment / 2 Bedrooms / Sleeps 5

from

$200

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:5
Type:Apartment
Per night:$200 - $250
Per month:$6,000 - $7,500
Pets allowed:Yes
Internet:Yes

This lovely 2 Bedroom sits in the Downtown/Gold Coast area. Voted in the top 5 areas that are 'walkable' No need for a car to see this lovely city! Although, there is a parking place provided if needed at no extra cost! Fully upgraded unit, with a fireplace, and balcony for your...

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Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$240

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$240
Per week:$1,680
Pets allowed:No
Internet:Yes

At Comfort Suite, we offer you a apartment designed to meet the needs of a relaxing vacation. Book with our Chicago studio; our great rates and friendly staff will help make your next trip more affordable and enjoyable. Get going with a great breakfast. Start your trip to Chicago...

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1 / 17

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 8
Apartment / 2 Bedrooms / Sleeps 8

from

$104

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:8
Type:Apartment
Per night:$104 - $114
Per week:$724 - $794
Pets allowed:Yes
Internet:Yes

Beautifully rehabbed with brand new eat- in kitchen and bath. Hardwood floors throughout apartment. All trim and woodwork has been magnificently restored to it's original look. Washer and dryer in unit Central air with individual controls for heat and AC. Guest love the huge outdoor...

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Chicago Illinois Vacation Rentals - Other
1 / 6

Chicago Other
1 Bedroom / 1 Bathroom / Sleeps 4
Other / 1 Bedroom / Sleeps 4

from

$285

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Other
Per night:$285
Per week:$1,995
Pets allowed:No
Internet:Yes

Hard Rock Hotel Chicago Enjoy downtown Chicago for work and play! Rock and relaxation take center stage at Hard Rock Tune into the good vibrations and relax in a world- famous cityscape at Hard Rock Hotel Chicago. Our hotel, housed in the historic Carbide & Carbon skyscraper,...

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1 / 17

Chicago Home
4 Bedrooms / 2.5 Bathrooms / Sleeps 20
Home / 4 Bedrooms / Sleeps 20

(1)“ Excellent ”1 Review

from

$800

/ night

Email Owner
Bedrooms:4
Bathrooms:2.5
Sleeps:20
Type:Home
Per night:$800 - $1,000
Per month:$24,000 - $30,000
Pets allowed:Yes
Internet:Yes

Gorgeous, huge, sun filled loft for a maximum of 12 guests. Very unique with antique skylights, timber ceiling, gourmet kitchen, and grand fireplace. We have 2 king beds, 1 full bed, and plenty of space for additional air mattresses. We have 2 full baths, and 1 half bath. ...

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Gorgeous venue!

“ Excellent ”
June 10, 2015
I rented the loft for a night to host a 50-people party and I had a great experience. The manager, John, is very kind and helpful - I had to move the check in time and he was happy to accommodate that. He also walked me around the property and explained me all i had to know for the party. The loft is a spectacular venue. Created in an old factory, the main room is gigantic and very bright thanks to the sky lights. The rooms have very interesting designs and there is even a staircase in an old chimney. We also really enjoyed the rooftop. The location is also great. The loft is very close to the CTA blue line (Western) in an happening area. It as the 90 Miles Cuban Cafe right next to it and a 24h Walgreen at 2 blocks. Highly recommended!
Luca Pizzuto, Chicago

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Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$241

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$241
Per week:$1,687
Pets allowed:No
Internet:No

Holiday Inn & Stes Chicago DT All of our contemporary guest rooms are 100% Non Smoking, equipped with free high- speed, WiFi access and a 32- inch HD TV with in- room movies. In addition, these rooms feature a comfortable triple- sheeted bed with a pillow top mattress and newly...

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Chicago Illinois Vacation Rentals - Condo
1 / 26

Chicago Condo
6 Bedrooms / 2 Bathrooms / Sleeps 16
Condo / 6 Bedrooms / Sleeps 16

(4)“ Excellent ”4 Reviews

from

$695

/ night

Email Owner
Bedrooms:6
Bathrooms:2
Sleeps:16
Type:Condo
Per night:$695 - $1,295
Per week:$4,865 - $9,065
Pets allowed:Yes
Internet:No

Chicago Vacation Rental lenience # 2320200 This well kept property sleeps 14 comfortably with space for two to four more on pull out couches. Enjoy the nice open one level floor plan and sunny interior. Additional bonus includes a a huge patio/ lounge with grill and garden. ...

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Excellent

“ Excellent ”
March 17, 2015
Great place, exactly as pictured. Our stay was enjoyable and hassle free. Owner was easily reached via email/text if needed.
Courtney Armstrong, Milwaukee, WI

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Chicago Illinois Vacation Rentals - Apartment
1 / 10

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3
Apartment / 1 Bedroom / Sleeps 3

(9)“ Excellent ”9 Reviews

from

$100

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:3
Type:Apartment
Per night:$100 - $180
Per week:$700 - $1,200
Pets allowed:No
Internet:Yes

Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop deck with poolside service, premier gym, wireless internet lounge, and much more. Overlooking 1, 200 acres of glorious Lincoln Park greenery and offering panoramic views of...

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949 W Madison St., Chicago, Illinois

“ Excellent ”
June 5, 2015
Excellent location; close to Downtown, Magnificent Mile and other attractions. Condo was clean and in excellent condition. I would recommend it to my friends.
Harry Koumarelas, Edmonton, Alberta, Canada

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Chicago Illinois Vacation Rentals - Condo
1 / 15

Chicago Condo
1 Bedroom / 1.5 Bathrooms / Sleeps 4
Condo / 1 Bedroom / Sleeps 4

(12)“ Excellent ”12 Reviews

from

$145

/ night

Email Owner
Bedrooms:1
Bathrooms:1.5
Sleeps:4
Type:Condo
Per night:$145 - $225
Per month:$4,350 - $6,750
Pets allowed:No
Internet:Yes

If you're looking for a quiet and quaint stay in Chicago that is minutes away from all of the downtown action, then the Casa in "Little Italy" is the vacation rental you've been looking for. The Casa will provide you with a taste of the lifestyle that most "Normal" people call life...

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Fantastic!

“ Excellent ”
June 2, 2015
The condo was incredibly clean and modern with all of the amenities to feel right at home. About five blocks over, there's a ton of restaurants, coffee shops and bars. The jacuzzi was a slice of paradise. Great location, we took a Lyft wherever we went and were there within 10-15 mins. Would definitely stay again!
Jim Jones, Lincoln, NE

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1 / 7

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4
Condo / 2 Bedrooms / Sleeps 4

(12)“ Excellent ”12 Reviews

from

$134

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
Per night:$134
Per week:$934
Pets allowed:No
Internet:No

, overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building amenities include work- out room, swimming pool, hot tub, parking, dry cleaners on- site, food market on- site....

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Fantastic all around!!

“ Excellent ”
June 27, 2015
This condo has an amazing view of both the lake and city! The placed has everything you need and is very comfortable. The doorman are the nicest men and extremely helpful. Joe was wonderful and Darrel was kind enough to make sure we were aware of how things work in a "city condo". You won't want to leave once you've spent a night!
Jennifer Sime Hartman, Utah

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Chicago Illinois Vacation Rentals - Apartment
1 / 7

Chicago Apartment
Studio / 1 Bathroom / Sleeps 4
Apartment / Studio / Sleeps 4

from

$185

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$185
Per week:$1,295
Pets allowed:No
Internet:No

Doubletree by Hilton Chicago From the warm and delicious DoubleTree cookie upon arrival, to the authentic Chicago hospitality and contemporary design, this downtown Chicago apartment will leave you with an unforgettable experience. Their home- like comforts and approachable staff...

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Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 4
Apartment / 1 Bedroom / Sleeps 4

from

$240

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Apartment
Per night:$240
Per week:$1,680
Pets allowed:No
Internet:Yes

Residence Inn Chicago Downtown/Mag Mile Experience the comforts of home in the Windy City at the Residence Inn Chicago Downtown/Magnificent Mile located in the posh Gold Coast district surrounded by upscale shopping and dining. Treat yourself to an exceptional Chicago Gold Coast...

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Chicago Illinois Vacation Rentals - Condo
1 / 6

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4
Condo / 1 Bedroom / Sleeps 4

from

$215

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$215
Per week:$1,505
Pets allowed:No
Internet:No

Homewood Suite by Hilton Chicago Downtown/Magnificent Mile. The spacious suite at this Magnificent Mile is ideal for extended- stay guests or families and feature full kitchens with refrigerators, microwaves, two- burner cooktops and dishwashers. Upgrade to a specialty suite...

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Chicago Illinois Vacation Rentals - Guesthouse
1 / 45

Chicago Guesthouse
5 Bedrooms / 2 Bathrooms / Sleeps 9
Guesthouse / 5 Bedrooms / Sleeps 9

(3)“ Excellent ”3 Reviews

from

$300

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:9
Type:Guesthouse
Per night:$300 - $499
Per week:$1,680 - $2,795
Pets allowed:No
Internet:Yes

Whether you are coming to Chicago for work or play (or both) Chicago Guest House is the absolute BEST choice for business & leisure travelers who want to experience the sense of having arrived 'home' while they are in Chicago! There Are 'Three' Apartments in this Building Located...

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Excellent properties

“ Excellent ”
December 30, 2009
We ended up staying at a smaller property owned by Teri due to the size of our group. It was delightful! Teri provided everything including Christmas decorations! She is the perfect hostess and the properties are exactly as described and better. You can't go wrong!!!
Pamela Winch-Matayoshi, SanDiego,CA

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About Chicago

Chicago, Illinois Travel Tips

Chicago, the biggest metropolitan city in the Midwest, teems with rich culture, an eclectic art scene, exciting nightlife, die-hard sports fans, and of course, deep-dish pizza. This city isn't just a great travel destination for adults; it also has much to offer families and kids of all ages. If you have started to look for Chicago condo rentals for your upcoming family vacation, be sure to check out the following travel tips that will help you and your family enjoy your time in the "Windy City".

Admire the Awesome Animal Life

Chicago is a fun destination for are animal-lovers of any size. With all of its entertainment options and aquatic life, a visit to The John G. Shedd Aquarium can fill up an entire day. From dolphin shows to a 400,000-gallon underground shark tank, the Shedd Aquarium is a fun outing for the whole family. Try to buy your tickets for the aquarium online, as this can save you both time and money the day of your trip. For families looking to save some money on attractions, a trip to the Lincoln Park Zoo is a must, as kids will enjoy watching the animals and parents will appreciate the free admission.

Enjoy a Day at the Museum

Chicago is home to several world-class museums, including many that will excite the kids. For dinosaur enthusiasts, don't miss the Field Museum, which is home to the largest tyrannosaurus rex skeleton ever uncovered. Other great museums for children include the LEGO Discovery Center, the Museum of Science and Industry, and the Children's Museum. If you wish to be in walking distance of certain museums, make sure to keep that in mind while searching through the Chicago condo rentals for your trip - it's all about location, location, location - especially for busy families.

Ride the attractions at Navy Pier

As one of the most popular attractions in Chicago, Navy Pier is a great place for both children and adults. There are many Chicago condos for rent that are perfectly located for easy access to the Navy Pier, which offers carnival-like rides, boat rides, a Ferris wheel, fun restaurants, and many more family-oriented attractions. If you plan on spending a significant amount of time at Navy Pier, check to see if there are any Chicago vacation rentals by owner that are within walking distance of this hot spot.

Easy and Unique Public Transportation

Chicago has one of the best public transportation systems in the country, which can be ...

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