Chicago Vacation Rentals, Apartments, & More

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Chicago Illinois Vacation Rentals - Apartment
1 / 11

Chicago Apartment
3 Bedrooms / 2.5 Bathrooms / Sleeps 8

“ Excellent ”39 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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Great location and views

“ Excellent ”
July 23, 2014
Views were exactly as pictured and location was perfect. Convenient parking. Management team was very accommodating. Shower pressure was just passable. That said would definitely stay here again.
Janie Hendricks, Iowa

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1 / 6

Chicago Condo
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ 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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1 / 8

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

These units have recently been renovated and includes hard wood floors, Granite countertops, Stainless steel appliances and georgus marble bathrooms. The high rise is just steps from Michigan Avenue and will sleep up to 6 people. Restaurants, cafes, convenience stores, movie ...

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Everything you need and more

“ Excellent ”
May 26, 2012
Modern building with all amenities and an apartment to match. Furniture, electronics and appliances were all first rate, worked fine, and most comfortable. Very roomy, filled with light, and a great place to stay in Chicago.
Bob Sugarman, Miami

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Chicago Illinois Vacation Rentals - Apartment
1 / 11

Chicago Apartment
3 Bedrooms / 1.5 Bathrooms / Sleeps 6

“ Excellent ”25 Reviews

from

$140

/ night

Email Owner
Bedrooms:3
Bathrooms:1.5
Sleeps:6
Type:Apartment
Per night:$140 - $235
Per month:$4,200 - $7,050
Pets allowed:No
Internet:Yes

Close to Downtown & McCormick Place. It's 10- 15 min by car or cab or a 15- 20 minute train ride from everything that Chicago has to offer. Please see our specials ad for our current specials. Our winter specials are our lowest rates of the year. You will be comfortable and...

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Outstanding Accommodations

“ Excellent ”
November 12, 2013
I want to give thanks to Bob for giving us the opportunity to stay at his vacation rental. It was in the perfect location and close to everything. We were able to sit up on the roof and watch the fireworks and for those rough days we could sit in the spa and the shower and sauna in the bathroom was amazing. I completely recommend this home for a long term and even short term vacation. Thanks again.
Sonia Mejia, Oceanside CA

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1 / 6

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ 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 / 17

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ 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 - Condo
1 / 37

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 6

“ Excellent ”23 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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Chicago visit

“ Excellent ”
October 6, 2014
The location of the property was great for our visit to Chicago! The apartment was clean and comfortable for my family of 5 . We had an initial issue with the apartment being too warm, but after a phone call the problem was readily rectified; which was a pleasant suprise!
Steve Emma, Lancaster, PA

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1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / 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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Chicago Illinois Vacation Rentals - Home
1 / 16

Chicago Home
2 Bedrooms / 1 Bathroom / Sleeps 10

from

$65

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:10
Type:Home
Per night:$65 - $134
Per week:$455 - $934
Pets allowed:Yes
Internet:Yes

ADDITIONAL SPACE AVAILABLE UPON REQUEST! Very affordable home in west suburb that offers easy access to the city. Sleeps up to 10 people. - 2 Bedrooms - 1 Bathroom - Hardwood Floors - Tiled Bathroom - Centrally controlled Heat and Air - Big back yard -...

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Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 Bedrooms / 2.5 Bathrooms / Sleeps 6

“ 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 - Condo
1 / 14

Chicago Condo
4 Bedrooms / 4 Bathrooms / Sleeps 14

from

$295

/ night

Email Owner
Bedrooms:4
Bathrooms:4
Sleeps:14
Type:Condo
Per night:$295 - $695
Per week:$2,065 - $4,865
Pets allowed:No
Internet:No

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 number 2314739 This building has 2 identical units one above the other. Both are beautiful 2 bedroom, 2 bath brand new ...

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Chicago Illinois Vacation Rentals - Condo
1 / 24

Chicago Condo
5 Bedrooms / 2 Bathrooms / Sleeps 16

“ Excellent ”3 Reviews

from

$600

/ night

Email Owner
Bedrooms:5
Bathrooms:2
Sleeps:16
Type:Condo
Per night:$600 - $1,200
Per week:$4,000
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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Cubs Hats Off to Angelina

“ Excellent ”
December 7, 2013
We just hosted a 4-night Thanksgiving extravaganza for family from both the East and West Coasts. We had 13 in all, including 4 kids, in Units 1 and 2. Angelina provided us with a table that easily accommodated everyone for the Thursday feast, which we cooked at the retreat. The place is great. First-class in all respects. KitchenAid and Viking in the kitchens. Outstanding WiFi service. Two of the 6 marble bathrooms even had rain showers. And the location is great, needless to say. Short walk to the Red Line (15 minutes to Macy's on State) and more bars than you will need in a lifetime. Uber taxis and black cars took just a few minutes to arrive. It was too cold to use the decks, but they are fully equipped. And there is a two car garage. Plus street permits. too. Thanks, Angelina!
John Henry Stassen, Chicago

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1 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ 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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1 / 15

Chicago Apartment
Studio / 1 Bathroom / 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 / 14

Chicago Apartment
2 Bedrooms / 1.5 Bathrooms / 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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Front Door To Biddle House
1 / 18

Chicago Guesthouse
4 Bedrooms / 2 Bathrooms / Sleeps 10

“ Excellent ”3 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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Biddle House 1st floor.

“ Excellent ”
June 4, 2012
My husband and I stayed at the Biddle House 1st floor apartment for six weeks in the Spring of 2012. We choose this property for several reasons: 1) the apartment was furnished; 2) this property welcomes families with dogs; 3) location-we were looking for an apartment in or near the Old Town Triangle neighborhood due to its' incredible charm and amenities; and 4) street parking was available and public transportation accessible. Our stay at the Biddle House was 6 weeks in total which I surmise is much longer than your average client who comes to Chicago for a long weekend or a week long stay. During our stay we enjoyed getting to know the staff of At Home Inn Chicago and all of our needs were handled by them in a very professional manner. We thoroughly enjoyed the neighborhood and its' friendliness was evident by the fact that we became acquainted with many of the neighbors who we met while on our daily dog walking routes. The apartment itself is in an historic home which dates back to the late 1800´s. The decor is quaint and tidy. The rooms are small yet comfortable for short stays. The kitchen feels like a cottage kitchen with just enough room for a sink, stove and refrigerator and if you want to prepare your own meals you must make due with just a few pots and pans. You are walking distance to many restaurants with carry out options and a great grocery store with fresh salad bar and good produce options. The highlight for us with this property is the location and the wonderful family and staff of At Home Inn Chicago.
Virginia Poynton, Chicago, Illinois

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Chicago Illinois Vacation Rentals - Condo
1 / 7

Chicago Condo
2 Bedrooms / 2 Bathrooms / Sleeps 4

“ Excellent ”11 Reviews

Bedrooms:2
Bathrooms:2
Sleeps:4
Type:Condo
No rental rates available - please contact the owner
 
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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Great time in Chicago

“ Excellent ”
October 27, 2014
Beautiful apartment, clean, well maintained, unbeatable location, close to the best downtown attractions, well furnished. I have nothing wrong to tell about it. We had a great time.
Silvia Restrepo, outside the US

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Chicago Illinois Vacation Rentals - Apartment
1 / 12

Chicago Apartment
2 Bedrooms / 2 Bathrooms / 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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Chicago Illinois Vacation Rentals - Townhouse
1 / 24

Chicago Townhouse
3 Bedrooms / 2 Bathrooms / 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 / 23

Chicago Apartment
2 Bedrooms / 1 Bathroom / Sleeps 6

from

$195

/ night

Email Owner
Bedrooms:2
Bathrooms:1
Sleeps:6
Type:Apartment
Per night:$195 - $250
Per week:$950 - $1,450
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 / 4

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

from

$270

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$270 - $340
Per week:$1,890 - $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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Chicago Illinois Vacation Rentals - Home
1 / 17

Chicago Home
4 Bedrooms / 3.5 Bathrooms / Sleeps 24

“ Excellent ”6 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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Beautiful house, great location!

“ Excellent ”
March 9, 2014
This house was truly amazing! Everything was just as pictured -impeccably clean, spacious, and beautifully designed. We had 11 people stay over the weekend, and 17 people for dinner one night, and we never once felt cramped or crowded. The main floor with the kitchen, dining, and living room areas easily accommodated everyone for dinner and conversation. If anyone needed any quiet space, the fully finished basement was perfect. Great outdoor space available - our only regret was that it was too early in the year (and too snowy!) to enjoy it. It was a great plus to have an attached 2 car garage, but there was also plenty of free/non-permit parking at front of the house and the surrounding streets. Close to restaurants, bars, and public transportation. I really cannot say enough about this place. I will definitely look into renting this house again for any future Chicago weekends with family and friends!
Julie Szablewski, Woodridge, IL

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1 / 9

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 5

“ 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 - Condo
1 / 24

Chicago Condo
3 Bedrooms / 1 Bathroom / Sleeps 7

“ Excellent ”8 Reviews

from

$225

/ night

Email Owner
Bedrooms:3
Bathrooms:1
Sleeps:7
Type:Condo
Per night:$225 - $250
Per week:$1,470
Pets allowed:No
Internet:Yes

Features 2 "independent" self catering units in the same building with fully functional kitchens. Coffee, tea, snacks, toiletries and all linen provided. Unit 1 - High 1st Floor: 3 bedrooms with a king size bed in master bedroom, 2 twin beds in 2nd bedroom, a queen size...

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A great place to stay for corporate travel!

“ Excellent ”
September 30, 2014
A group of employees from our company stayed in Unit 1 for a week while attending a trade show downtown. The owner was very accommodating to our needs and flexible with their time frame. The neighborhood is quiet and bike friendly. We were all impressed by how many restaurants and coffee shops were just within walking distance. When we arrived at the house, we were greeted by an inviting and well-kept space. The unit was exactly as the pictures had shown. The bedding was all comfortable and we appreciated the lightly stocked kitchen and pantry. After longs days on our feet at a trade show, it was relaxing to return to an actual living space like this unit as compared to a hotel room. We had no problems with any of the appliances or electronics. Since we did have 5 people staying in the unit, it was difficult at times to share just one bathroom. But other than that, we have not one complaint. Now that our stay is over, I would say the rental price for this unit is a great deal. Staying in this rental unit made our stay in Chicago extremely enjoyable. We would stay again!
Lauren Busch, Pittsburgh, PA USA

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Chicago Illinois Vacation Rentals - Condo
1 / 10

Chicago Condo
10 Bedrooms / 8 Bathrooms / Sleeps 20

from

$50

/ night

Email Owner
Bedrooms:10
Bathrooms:8
Sleeps:20
Type:Condo
Per night:$50 - $60
Per week:$350
Pets allowed:No
Internet:Yes

Independent Bedroom Close to Downtown Chicago 18th dorm is located on heart of Pilsen. the six corner intersection of Blue Island/Loomis & 18Th St. Mins to downtown Chicago, UIC. 2 Blocks to pink line. 2 bus stops front of the building. All public transportation are directly to ...

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Living Area with Queen Pull-Out Sofa
1 / 9

Chicago Apartment
Studio / 1 Bathroom / Sleeps 2

from

$89

/ night

Email Owner
Bedrooms:Studio
Bathrooms:1
Sleeps:2
Type:Apartment
Per night:$89 - $109
Per week:$623 - $763
Pets allowed:Yes
Internet:Yes

Note: 30 Night Minimum Stay 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop in Downtown Chicago - Five Blocks West of Michigan Avenue and Millenium Park 'Bean'; In Business/Theater District) This high- end unit has granite countertops, stainless steel...

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1 / 8

Chicago Apartment
2 Bedrooms / 2 Bathrooms / Sleeps 3

“ Excellent ”1 Review

from

$92

/ night

Email Owner
Bedrooms:2
Bathrooms:2
Sleeps:3
Type:Apartment
Per night:$92
Per week:$642
Pets allowed:No
Internet:No

Elegant private large one bedroom apartment, large comfortable living room, close to the lakefront, 12 min to downtown, upscale residential neighborhood, greatly maintained building, stylish, great long term. Minimum 30 days rental also long term rental as furnished apartment,...

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Incredible!

“ Excellent ”
July 15, 2011
This property has all the features one could want in a vacation home. It is close to downtown Chicago, walking distance to Wrigley Field, and across the street from the lake. It is exceptionally well-kept and very comfortable. I would recommend it to anyone.
Emily Barsh, Stillwater, Ok

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Chicago Illinois Vacation Rentals - Home
1 / 13

Chicago Home
5 Bedrooms / 3 Bathrooms / Sleeps 11

“ Excellent ”8 Reviews

from

$459

/ night

Email Owner
Bedrooms:5
Bathrooms:3
Sleeps:11
Type:Home
Per night:$459 - $499
Per week:$3,213 - $3,493
Pets allowed:No
Internet:Yes

Enjoy this newly completed high- end renovation of a classic Brownstone home with 5 spacious bedrooms, 3 full baths and home theater equipped living rooms. This beautiful home is located on a quiet, tree lined street on the Northside of Chicago. Located in the Lincoln Square neighborhood,...

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Lovely place!

“ Excellent ”
March 19, 2013
This place was great! It's in a good location, very clean, close to super market, which was very convenient. It was a group of 11 and we all fit very comfortably! There were a few things that prevented me from giving the place a 5 One was the jacuzzi had something wrong with it, and would periodically throughout the night until it went though a cycle. It would have been nice, if the owner let us know ahead of time, so we didn't use it, especially since we used it at night and it did not turn completely off until about 2am. Also the TV's were difficult at times, but we got a handle on it after a while. Again, just some minor things, but after the jacuzzi was off and we figured out the TV's we had a great time and enjoyed the house! We would definitely go again!
Donna Betsy, New York, NY USA

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Chicago Illinois Vacation Rentals - Condo
1 / 9

Chicago Condo
1 Bedroom / 1 Bathroom / Sleeps 4

“ Excellent ”6 Reviews

from

$149

/ night

Email Owner
Bedrooms:1
Bathrooms:1
Sleeps:4
Type:Condo
Per night:$149 - $250
Per week:$1,170 - $1,350
Pets allowed:No
Internet:Yes

Are you planning a trip to Chicago? Why stay in an expensive hotel room when you can rent furnished luxury condos, some with PENTHOUSE views of downtown Chicago and the lake. We stay in the apartments so they are stocked with most anything you would need to cook and entertain with....

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Chicago Andersonville/Uptown/Edgewater Made Easy!

“ Excellent ”
July 15, 2013
We stayed at the Metro Tower for five nights, the apartment was very comfortable and even more spacious than the pictures suggested (we had a one bedroom) the views of the lake beautiful. You can walk to the beach literally in five minutes. The location and parking made getting around so easy. Dominick's grocery store is half a block away with free parking. Great restaurants and neighborhoods in every direction. Booking was easy and no pressure which I appreciated. Check-in and check-out could not have been simpler. The front door security people were so nice and always greeted us with a smile and have a nice day! In fact the only problem was me and Bill was never phased he always just replied "Really, it's no problem!" and helped me out whether it was the dates I kept changing, the map I lost, the clothes I left in the room...ugg! I hope we can stay here again sometime soon, so much better than fighting downtown crowds and small hotel rooms.
Rf Johnson, Sterling,IL

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Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
4 Bedrooms / 2 Bathrooms / Sleeps 8

“ 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 / 5

Chicago Apartment
2 Bedrooms / 1 Bathroom / 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 / 10

Chicago Apartment
1 Bedroom / 1 Bathroom / Sleeps 3

“ Excellent ”8 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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Couldn't have been better!

“ Excellent ”
July 23, 2013
This was the nicest most accommodating vacation spot I have ever stayed in. The condo had everything from separate pool towels to night lights. I stayed with my husband and two young daughters. There was plenty of room, the view was amazing and we walked everywhere! The building staff and other residents were all very kind as well. We will definitely stay here again the next time we're in Chicago!
Holly Nick Koehler, St. Louis, MO

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Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
3 Bedrooms / 2 Bathrooms / Sleeps 8

from

$350

/ night

Email Owner
Bedrooms:3
Bathrooms:2
Sleeps:8
Type:Apartment
Per night:$350 - $395
Per week:$2,450 - $2,765
Pets allowed:No
Internet:Yes

Spacious Bright Vacation Rental Loft in the Heart of Everything Chicago sleeps - 2 - 9 Guests Brand new listing - the reviews are coming! Our funky warehouse & former tavern turned costume factory turned fabulous Lincoln Park home can be your home away from home in Chicago....

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Chicago Illinois Vacation Rentals - Guesthouse
1 / 45

Chicago Guesthouse
5 Bedrooms / 2 Bathrooms / Sleeps 9

“ 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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Hot Tub / Jacuzzi
1 / 15

Chicago Condo
1 Bedroom / 1.5 Bathrooms / Sleeps 4

“ Excellent ”11 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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Little Italy Condo

“ Excellent ”
August 25, 2014
Tracy & Raphael were great in terms of responding to questions I had. Pros include an absolutely beautiful location, just a minute walk away from Taylor St. Even more luckily for us, Festa Italia was going on while we were there and we spent every night perusing all the food and wine there.The actual place was pretty neat. There was a huge hot tub in the LL that doubled as a "mini-pool" for my kids. It was well decorated and roomy and had almost everything you would need for a starter kitchen. And for being so close to Festa Italia, it was actually very quiet and felt very safe. We went to the Shedd/Children's Museum/Adler area almost every day and it was only about a 20 minute car ride. And best of all (for parents) is that Tracy & Raphael already installed a baby gate for the basement stairs and had a high chair there waiting for us.Con's: the bathroom floor was... not cleaned. And neither was the floor under the bed or sofas.But overall, we actually want to use this condo again in the future for our Chicago trips.
Marine Yoo, Madison, WI

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Bedrooms:3
Bathrooms:1
Sleeps:5
Type:Apartment
No rental rates available - please contact the owner
 
Pets allowed:No
Internet:Yes

First floor furnished unit of an owner- occupied two- flat has three bedrooms - two large and one small. There are hardwood floors throughout the apartment. Wooden blinds in the livingroom and vinyl mini- blinds throughout the rest of the apartment. The living room, dining room ...

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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 extremely beneficial for visitors, especially those traveling with children. Not only is public transportation inexpensive, but kids can also experience riding the L-train - the elevated train that provides great views of downtown Chicago. If you plan on taking public transportation during your trip, choose from our selection of Chicago condos for rent close to a train station or bus stop.
If you are trying to find the perfect family vacation destination that offers a wide variety of options for condo rentals, Chicago is a great choice! Searching for condo rentals doesn't need to be challenging; we're here to help you find a place that fits all of your family's needs and aim to help you plan a memorable and comfortable family vacation. We provide a variety of vacation rentals by owner, Chicago and surrounding areas. With these affordable and fitting accommodations, Chicago might just be your new favorite family vacation spot.
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