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Chicago Vacation Rental Listings

Our Chicago Vacation Rentals selection includes only the best Chicago homes, condos, villas, hotels, bed & breakfasts, cabins, and cottages.

Listed below, you will find numerous Chicago lodging and accommodations to suit your needs. Click on the view details button to explore any of the Chicago rentals you see listed for more information. Illinois, Chicago Vacation Rentals are continuously added and modified, so if you do not find what you are looking for in our Chicago Vacation rental inventory, make sure you bookmark us and come back frequently.

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Lincoln Park Oasis - Vacation Rental in Chicago

Lincoln Park Oasis - Chicago

8 Bedrooms
Sleeps 18
From USD150.0 nt

• Utensils
• Stove - Gass
• Refrigerator
• Microwave
• Full Kitchen
• Dishwasher

Beautiful Victorian in the heart of Lincoln Park, great/safe neighborhood of Chicago. Close to Park, cafes & restaurants and DePaul University. Will provide free visitor parking permits. Easy Parking, six minutes walk from public transportation - CTA
*Check to inquire


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Close to Shopping, Dining, North Ave Beach - Vacation Rental in Chicago

Close to Shopping, Dining, North Ave Beach - Chicago

1 Bedrooms
Sleeps 4
From USD220.0 nt

• Sauna
• Pool
• Jacuzzi/Hot Tub
• Garage
• Utensils
• Stove - Electric

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 off
*Check to inquire


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House of Two Urns B&B and Apartments - Bed and Breakfast in Chicago

House of Two Urns B&B and Apartments - Chicago

10 Bedrooms
Sleeps 24
From USD75.0 nt

• Jacuzzi/Hot Tub
• Garage
• BBQ
• Utensils
• Stove - Gass
• Stove - Electric

Charming urban Chicago Bed and Breakfast guestrooms or 3 apartments available for rent for short term rentals. We are conveniently located in Wicker Park, a hip urban Chicago neighborhood, just 4 minutes to downtown (the loop) via car or subway and 15
*Check to inquire


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The Arlington House int値 Hostel - Hotel/Motel in Chicago

The Arlington House int値 Hostel - Chicago

Studio
 
From USD31.0 nt

• Refrigerator
• Microwave
• Coffee Maker
• High Speed Internet
• Air Conditioning

The Arlington House, Chicago, has recently undergone extensive renovations, and our features include a full kitchen, media lounge and a game room as well as vending machines and free internet access. We provide linens and towels and housekeeping. We a
*Check to inquire


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At Home Inn Chicago - Vacation Rental in Chicago

At Home Inn Chicago - Chicago

30 Bedrooms
Sleeps 75
 


Your vacation or business travel to Chicago will be greatly enhanced by your reservation at one of our over 60 different lodging choices--inns, guest houses, furnished apartments and bed & breakfast accommodations. All of the accommodations are locate
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CENTENNIAL HOUSES of Lincoln Park - Vacation Rental in Chicago

CENTENNIAL HOUSES of Lincoln Park - Chicago

 
Sleeps 15
 

• Air Conditioning
• CD Player
• Fireplace
• High Speed Internet
• Linens provided
• Phone

Private apartments in 1891 home or individual guestrooms in 1886 historic mansion, both in downtown's most upscale neighborhood. Beautifully decorated with fine European and American 19th century antiques and artwork yet with 21st century amemities su
*Check to inquire


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THE CHINA DOLL GUEST HOUSE - Vacation Rental in Chicago

THE CHINA DOLL GUEST HOUSE - Chicago

2 Bedrooms
Sleeps 8
From USD225.0 nt

• Jacuzzi/Hot Tub
• BBQ
• Utensils
• Stove - Gass
• Refrigerator
• Microwave

In Chicago痴 Lincoln Park neighborhood, China Doll offers three complete self-contained apartment suites with private entrances. There is a two-room/one bedroom unit and two six-room/two bedroom units. Designed as a corporate apartment, the office are
*Check to inquire


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Flemish House of Chicago - Bed and Breakfast in Chicago

Flemish House of Chicago - Chicago

 
Sleeps 3
From USD175.0 nt


Welcome to THE FLEMISH HOUSE, where you are at home in Chicago! This elegant yet charming Chicago Bed and Breakfast offers serviced apartments with stocked kitchens in downtown Chicago, steps from Michigan Avenue shopping, Oak Street Beach and our mag
*Check to inquire


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Downtown Chicago Luxury Condos - Vacation Rental in Chicago

Downtown Chicago Luxury Condos - Chicago

3 Bedrooms
Sleeps 10
From USD220.0 nt

• Pool
• Covered Parking
• BBQ
• Utensils
• Stove - Electric
• Refrigerator

Choose from three condos in the fabulous Gold coast Location. Our 1bed/1bath units on the 55th and 54th floor have the most spectacular views in Chicago, as does our 2bed/2bath unit on the 48th floor. Either way the city lights up like a Christmas tre
*Check to inquire


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Abode Ltd. - Bed and Breakfast in Chicago

Abode Ltd. - Chicago

2 Bedrooms
Sleeps 4
 

• Air Conditioning
• Cable/Satellite TV
• CD Player
• High Speed Internet
• Linens provided
• Stereo

Abode by definition is home. We offer you the comfort and convenience of our home when you must be away from your own. For those who prefer heights there is the Tree-Line unit and for those who prefer to remain close to the earth, our Garden unit will
*Check to inquire


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University Quarters Bed & Breakfast & Suites - Bed and Breakfast in Chicago

University Quarters Bed & Breakfast & Suites - Chicago

6 Bedrooms
Sleeps 12
From USD125.0 nt

• Jacuzzi/Hot Tub
• Utensils
• Refrigerator
• Microwave
• Ice Maker
• Full Kitchen

With six, gracious guest rooms and full-floor suites, University Quarters Bed & Breakfast & Suites occupies the entire First Floor and Garden levels of a lovely, vintage, totally updated greystone one-half block from The University of Chicago campus.
*Check to inquire


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The Westin Michigan Avenue Chicago - Hotel/Motel in Chicago

The Westin Michigan Avenue Chicago - Chicago

 
 
 


Location. Located in the center of famed shopping along North Michigan Avenue's prestigious address, The Westin Michigan Avenue Chicago (Ill.) sits one block from Water Tower Place. Within four blocks of the hotel are Rush Street dining and nig
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Hotel Allegro Chicago - A Kimpton Hotel - Hotel/Motel in Chicago

Hotel Allegro Chicago - A Kimpton Hotel - Chicago

 
 
 


Location. Located within the Chicago Loop business and theater districts, the Hotel Allegro Chicago (Ill.) is adjacent to the Cadillac Palace Theatre, a 1926 vaudevillian showcase theater that features Broadway shows and Tony Award winning play
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Radisson Hotel & Suites - Downtown Chicago - Hotel/Motel in Chicago

Radisson Hotel & Suites - Downtown Chicago - Chicago

350 Bedrooms
 
 


Location. The Radisson Hotel & Suites Chicago rests one half block from Michigan Avenue's Magnificent Mile and two blocks from American Girl Place. Three blocks from the property are Lake Michigan and the historic Old Water Tower. Other histori
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PARK HYATT CHICAGO - Hotel/Motel in Chicago

PARK HYATT CHICAGO - Chicago

 
 
 

• High Speed Internet
• Coffee Maker

PROPERTY DESCRIPTIONFLAGSHIP OF THE PARK HYATT BRAND, OFFERING A UNIQUEALTERNATIVE TO YOUR TRAVELER S CURRENT 5 STAR OPTIONS. STATEOF THE ART GUEST ROOMS FEATURING DVD/CD PLAYERS, FLAT SCREENTV, HIGH SPEED INTERNET ACCESS. LUXURY BATHROOMS WITHOVERSIZ
*Check to inquire


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