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Chicago Illinois Vacation Rentals - Bed & Breakfast
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Chicago Bed & Breakfast
7 BR / 8 BA / Sleeps 16 7 16 1 night min stay
Bed & Breakfast / 7 Bedrooms / Sleeps 16
7 bedrooms 8 bathrooms Sleeps 16
High Speed Internet • Microwave • Washer/Dryer
7 gorgeous units! Celebrity themed.. The first three floors are made up of a one bedroom and a studio and the fourth floor is a two bedroom suite. A common area downstairs that leads to the back garden area with fire an...
Chicago Illinois Vacation Rentals - Condo
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Chicago Condo
4 BR / 4 BA / Sleeps 12 4 12 No min stay
Condo / 4 Bedrooms / Sleeps 12
4 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
This unit is located on two floors. Ideal for families and groups traveling together and also traveling with nanny's. Two Kitchens, One Larger kitchen fully equipped and brand new also a wet bar for entertaining and wal...
Chicago Illinois Vacation Rentals - Apartment
1 / 6

Chicago Apartment
1 BR / 1 BA / Sleeps 3 1 3 No min stay
Apartment / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
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 th...
(6) Excellent (6 reviews)
Chicago Illinois Vacation Rentals - Apartment
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Chicago Apartment
3 BR / 1.5 BA / Sleeps 6 3 6 No min stay
Apartment / 3 Bedrooms / Sleeps 6
3 bedrooms 1.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Most dates in Summer have a 5 night minimum. We have 3 nights available June 30th through July 3rd and 4 night available July 9th through July 13th. We have been offering our rentals for 8 years now. We have over 200...
(27) Excellent (27 reviews)
Chicago Illinois Vacation Rentals - Home
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Chicago Home
4 BR / 3.5 BA / Sleeps 24 4 24 Min stay varies
Home / 4 Bedrooms / Sleeps 24
4 bedrooms 3.5 bathrooms Sleeps 24
High Speed Internet • Dishwasher • Microwave
Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home which is fully licensed by the City #2262746! Don't trust places which don't have a license! Check out ChicagoHome. Vacat...
(10) Excellent (10 reviews)
Chicago Illinois Vacation Rentals - Condo
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Chicago Condo
1 BR / 1 BA / Sleeps 4 1 4 No min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
TV (Antenna) • Air Conditioning • Parking Included
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 a...
(6) Excellent (6 reviews)
Chicago Illinois Vacation Rentals - Apartment
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Chicago Apartment
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
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 bloc...
Chicago Illinois Vacation Rentals - Apartment
1 / 42

Chicago Apartment
3 BR / 1 BA / Sleeps 8 3 8 No min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 1 bathroom Sleeps 8
Dishwasher • Microwave • Washer/Dryer
This vacation property is in a large vintage brownstone on a quiet, tree- lined street in Buena Park, a historic area in the southeast corner of Chicago's Uptown neighborhood. The place is a little over a mile walk to ...
(1) Excellent (1 review)
Chicago Illinois Vacation Rentals - Home
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Chicago Home
5 BR / 3 BA / Sleeps 12 5 12 No min stay
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 3 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
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 o...
(12) Excellent (12 reviews)
Chicago Illinois Vacation Rentals - Apartment
1 / 8

Chicago Apartment
1 BR / 1 BA / Sleeps 4 1 4 3 night min stay
Apartment / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • Air Conditioning
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 ve...
Chicago Illinois Vacation Rentals - Condo
1 / 37

Chicago Condo
2 BR / 2 BA / Sleeps 6 2 6 No min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
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 visi...
(26) Excellent (26 reviews)
Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 BR / 2.5 BA / Sleeps 6 3 6 No min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2.5 bathrooms Sleeps 6
Dishwasher • TV (Antenna) • Air Conditioning
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 ...
(1) Excellent (1 review)
Chicago Illinois Vacation Rentals - Condo
1 / 5

Chicago Condo
3 BR / 2.5 BA / Sleeps 10 3 10 No min stay
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2.5 bathrooms Sleeps 10
Dishwasher • Microwave • Air Conditioning
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 ...
Chicago Illinois Vacation Rentals - Apartment
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Chicago Apartment
3 BR / 2.5 BA / Sleeps 8 3 8 No min stay
Apartment / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
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 A...
(42) Excellent (42 reviews)
Chicago Illinois Vacation Rentals - Studio
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Chicago Studio
-1 BR / 1 BA / Sleeps 2 -1 2 No min stay
Studio / -1 Bedroom / Sleeps 2
-1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Washer/Dryer • TV (Antenna)
Stunning Space Features wall to wall upgraded plush carpeting, beautiful open kitchen with granite countertops and stainless steel appliances, massive walk in closet with loads of storage space, floor to ceiling windo...
Chicago Illinois Vacation Rentals - Apartment
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Chicago Apartment
1 BR / 1 BA / Sleeps 2 1 2 No min stay
Apartment / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Washer/Dryer • TV (Antenna)
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 o...
Chicago Illinois Vacation Rentals - Apartment
1 / 12

Chicago Apartment
2 BR / 1 BA / Sleeps 4 2 4 30 night min stay
Apartment / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
Located in BEAUTIFUL Roscoe Village. Eat in kitchen with attached dining room. Garage available and shared backyard. Refinished floors, woodwork and built ins. Central AC with stacked washer/dryer in unit. Pets on case ...
Chicago Illinois Vacation Rentals - Apartment
1 / 12

Chicago Apartment
3 BR / 3 BA / Sleeps 10 3 10 30 night min stay
Apartment / 3 Bedrooms / Sleeps 10
3 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Located in the heart of Bucktown. Short term or long term stays available. Just bring your suitcase. This is set up for corporate/family stays with silverware, glassware, plates, bowls, silverware, etc., etc. Stain...
Chicago Illinois Vacation Rentals - Townhouse
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Chicago Townhouse
3 BR / 2.5 BA / Sleeps 8 3 8 5 night min stay
Townhouse / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Gorgeous, Luxury Oak Park area Townhome... corner unit... completely furnishedclose proximity (2 min. ) to the historic Oak Park area... home of Frank Lloyd Wright and Ernest Hemingway! Beautiful landscaping, tota...
Chicago Illinois Vacation Rentals - Apartment
1 / 37

Chicago Apartment
1 BR / 1 BA / Sleeps 2 1 2 No min stay
Apartment / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Dishwasher • Washer/Dryer
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 an...
Chicago Illinois Vacation Rentals - Condo
1 / 7

Chicago Condo
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Beautifully done high- end furnished 3 bedroom | 2 bath | located downtown Chicago
(7) Excellent (7 reviews)
Chicago Illinois Vacation Rentals - Condo
1 / 16

Chicago Condo
3 BR / 2 BA / Sleeps 6 3 6 3 night min stay
Condo / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Posh 3 bedroom condo located downtown Chicago. VERY VERY near all major attractions and accessible via Train- Bus. Spacious with Beautiful Skyline and Lake Views.
(1) Excellent (1 review)
Chicago Illinois Vacation Rentals - Condo
1 / 4

Chicago Condo
1 BR / 1 BA / Sleeps 4 1 4 3 night min stay
Condo / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • DVD Player • TV (Cable/Satellite)
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 s...
Chicago Illinois Vacation Rentals - Apartment
1 / 16

Chicago Apartment
1 BR / 1 BA / Sleeps 2 1 2 No min stay
Apartment / 1 Bedroom / Sleeps 2
1 bedrooms 1 bathroom Sleeps 2
High Speed Internet • Washer/Dryer • TV (Antenna)
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 spac...
Chicago Illinois Vacation Rentals - Apartment
1 / 9

Chicago Apartment
2 BR / 2 BA / Sleeps 5 2 5 3 night min stay
Apartment / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
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, stai...
(4) Excellent (4 reviews)
Chicago Illinois Vacation Rentals - Guesthouse
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Chicago Guesthouse
5 BR / 2 BA / Sleeps 9 5 9 3 night min stay
Guesthouse / 5 Bedrooms / Sleeps 9
5 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
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 C...
(3) Excellent (3 reviews)
Chicago Illinois Vacation Rentals - Home
1 / 23

Chicago Home
3 BR / 3 BA / Sleeps 7 3 7 4 night min stay
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 3 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
5- star rating with great reviews. HOME SUMMARY... Gorgeous, sun- filled 2100 sq ft single- family home set- up over 3 levels offers privacy and space for you and your guests. This serene, totally resort- like ho...
(1) Excellent (1 review)
Chicago Illinois Vacation Rentals - Condo
1 / 21

Chicago Condo
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
You won't find a better location than this bright and comfortable vacation rental, which is perfectly maintained to accommodate your needs away from home. The cta train is close and walking distance, and the bus stop i...
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About Chicago

Built on the shores of Lake Michigan and known for its rich culture, die-hard sports fans and of course, deep-dish pizza, Chicago, Illinois is abuzz with action and welcomes millions of visitors annually. Here, choose from a variety of Chicago vacation rentals in the city’s 77 neighborhoods then enjoy the area’s welcoming, mid-western hospitality. Below is some need-to-know information before visiting the “Windy City.”

Transit

Downtown Chicago is easy to navigate with its street grid setup. Its wide sidewalks, lakefront paths and extensive parklands make it a scenic walking city. For cyclists, Chicago’s bike sharing program, Divvy, is very popular and the city’s many bike lanes and bike racks accommodate riders. In addition to its pedestrian and cyclist-friendly layout, Chicago has one of the best and largest public transportation systems in the country, which can be extremely beneficial for visitors, especially those traveling with children. Not only is public transportation inexpensive, it gives riders unique views of the city’s downtown from its elevated “L” trains. If you plan on using public transportation, choose from a variety of Chicago condo rentals near a train station or bus stop.

Things to Do

Whether you’re a foodie or a shopaholic, looking for an action-packed outing or a laughter-filled evening, Chicago has it all. The city’s Navy Pier juts into Lake Michigan and offers carnival-like rides like a Ferris wheel, family-oriented museums, funky restaurants and beer gardens. Away from the lakeshore, the Chicago Zoo is camouflaged within the heart of the city. It’s a natural oasis offering loads of wildlife shaded by skyscrapers. Kids will love watching the animals while parents will appreciate the free admission. In season, catch a game at Wrigley Field or cheer on the beloved Blackhawks and Bulls at the United Center. A trip to Chicago would not be complete without strolling through Chicago’s art-filled Millenium Park before snapping a picture in front of the city’s signature landmark, Cloud Gate.

Dining

With 77 neighborhoods, each with their own tastes and cultural influences, the city’s food scene is a melting pot of flavors. Have a taste-off between Lou Malnati’s and Giordano’s to decide on the best deep dish pizza. Dine alfresco at The Terrace at Trump or enjoy casual eats at The Little Goat Diner. Bring your appetite as you’ll never go hungry in Chicago.

Shopping

For fashionistas, Magnificent Mile is a dream-come-true. This shopping area is lined with upscale department stores like Bloomingdale’s and Macy’s on Michigan Avenue and iconic Chicago landmarks like the Tribune Tower and the Wrigley Building give it a majestic feel. Here you’ll find Water Tower Place, an eight-story mall with mainstream stores and the flagship American Girl store. Downtown along the Chicago Loop is Fannie May Chocolates where you can pick up sweet treats to bring home for your friends.

Arts & Entertainment

Chicago is home to many world-class museums, including many that will excite the kids. Dinosaur enthusiasts love the Field Museum where the largest tyrannosaurus rex skeleton resides. Other great, family-friendly museums include the Museum of Science and Industry, the Children’s Museum and the LEGO Discovery Center. You don’t even have to go to a museum though to see impressive art displays as Chicago has a large collection of public art displayed along city streets and gardens. Once the sun sets, Chicago’s nightlife comes alive.  Laugh your head off at The Second City where famed comedians launched their careers, or see an original play at one of Chicago’s 200+ theaters.

If you’re looking for the perfect city vacation, put Chicago at the top of your list. Stay sky-high in Chicago apartment rentals or book waterfront vacation rentals for spacious luxury. Wherever you are though, you’ll never be far from the action and Chicago might just become your new favorite vacation spot.