Vacation Rentals in Chicago, IL

Search and compare Chicago, IL vacation rentals from hundreds of travel sites and save

Chicago, IL, United States
5 Oct — 6 Oct2
Chicago, IL, United States
Wed 5/10
Thu 6/10
...and more

Tips for booking vacation rentals in Chicago

Cheapest month:January
Most expensive month:June
Average price in Chicago:C$ 436/night
Cheapest price found:C$ 56/night
Cheapest day:Tuesday
Most expensive day:Friday
C$ 149 - C$ 803
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
C$ 235 - C$ 384
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Top Rated Chicago vacation rentals

1
The Chicago Hotel Collection Millennium Park
5.5 Okay
55 East Washington Street, Chicago, IL, United States
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0.8 km from city centre, Chicago, IL, United States 

Centrally situated, Pittsfield Apartments + Suites allows for easy access to Chicago's best hot spots. It offers complimentary Wi-Fi, an express check-in and check-out feature and a swimming pool.

Cheapest vacation rentals in Chicago, Illinois

Furnished Suites in South Loop Chicago
Chicago, IL, United States
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1.2 km from city centre, Chicago, IL, United States 

Strategically located in the heart of the city, this 4.5-star property makes for an ideal base in Chicago. It also offers laundry facilities, a concierge and free Wi-Fi.

C$ 97
Avg. per night
The Penthouse at Grand Plaza
9.3 Excellent
540 North State Street, Chicago, IL, United States
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1.8 km from city centre, Chicago, IL, United States 

Conveniently located in the middle of the city, this 4-star property makes for an excellent base in Chicago. It offers an outdoor pool, a sauna and complimentary Wi-Fi access.

C$ 439
Avg. per night
Ginosi 747 Apartel
Chicago, IL, United States
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3.2 km from city centre, Chicago, IL, United States 

Ginosi 747 Apartel is located in Chicago and features complimentary Wi-Fi. It is situated a brief walk from the Polish Museum of America.

C$ 445
Avg. per night
Corporate Suites in the Heart of Magnificent Mile
Chicago, IL, United States
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1.8 km from city centre, Chicago, IL, United States 

Strategically located in the centre of the city, this 4-star property makes for an excellent base in Chicago. It offers an indoor pool and free Wi-Fi, and is a brief stroll from Michigan Avenue and Magnificent Mile.

C$ 676
Avg. per night
Apartment in River North with Balcony
Chicago, IL, United States
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2.5 km from city centre, Chicago, IL, United States 

This comfortable property in Chicago offers complimentary wireless internet, as well as an outdoor pool and a swimming pool. It is conveniently located in the city centre.

C$ 706
Avg. per night
Celeste Celebrity Suites
Chicago, IL, United States
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3.0 km from city centre, Chicago, IL, United States 

Centrally located, Celeste Celebrity Suites offers easy access to Chicago's best hot spots. It provides free Wi-Fi and room service, and is a brief stroll from John Hancock Center, Michigan Avenue and John Hancock Center Observatory.

C$ 1,190
Avg. per night

Vacation rental prices in Chicago

3 stars
4 stars +

Best prices found by HotelsCombined users in the past 24 hours.

Where to stay in Chicago

Facts about staying in Chicago

  • How much does a vacation rental in Chicago cost?

    Chicago vacation rentals are C$ 319/night on average. However, you may find that prices fluctuate depending on the time of year. For example, November is the most expensive month to book a vacation rental in Chicago, and September is often the cheapest month to book. Recently, our users found rentals for C$ 57/night - which is currently the cheapest price. Keep in mind that anything C$ 246/night or less is still considered a good deal.

  • What is the best Chicago vacation rental?

    The Chicago Hotel Collection Millennium Park has a 5.5 rating from 185 users, making it the best Chicago vacation rental based on our data.

  • What’s the closest vacation rental to Chicago O'Hare Intl Airport?

    It’s only 19.3 km from Chicago O'Hare Intl Airport to Sonder - The Western (the nearest Chicago vacation rental to the airport).

  • What part of Chicago is best to stay in?

    Downtown is the best part of Chicago to stay in based on our user data. Out of all our users who looked at Chicago vacation rentals, 1% of them looked for stays in the Downtown neighbourhood in the last year. The 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena happens to be the most popular vacation rental in the Downtown neighbourhood of Chicago.

  • What’s the most popular vacation rental in Chicago near Navy Pier?

    If you’re looking for a vacation rental close to Navy Pier while in Chicago, then the most popular is The Chicago Hotel Collection Millennium Park with a 5.5/10 review score from 185 users. The distance from Navy Pier to The Chicago Hotel Collection Millennium Park is 2.0 km.