Vacation Rentals in Chicago, IL

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

Chicago, IL, United States
4 Apr — 5 Apr2
Chicago, IL, United States
Thu 4/4
Fri 5/4
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Popular holiday rental in Chicago

Discover well-known properties in Chicago that are favoured by visitors more than others. There are 3,023 hotels in Chicago and price data was last updated on 28 March 2024. The average price for a hotel in Chicago is C$ 418/night.
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747 North May Street, 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.
Free Wi-Fi
Air Conditioning
Location
3.2 km from city centre
C$ 654
540 North State Street, Chicago, IL, United States
Conveniently located in the middle of the city, this 4-star property makes for an excellent base in Chicago. It also offers a sauna, an outdoor pool and free Wi-Fi.
Free Wi-Fi
9.2
Excellent
63 reviews
Location
1.8 km from city centre
C$ 586
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.
Air Conditioning
Location
2.5 km from city centre
C$ 318

Tips for booking vacation rentals in Chicago

Gain useful insights and advice for booking the perfect stay in Chicago. Price data is based on averages over the past 12 months and was last updated on 28 March 2024.
Cheapest month:May
Most expensive month:July
Average price in Chicago:C$ 418/night
Cheapest price found:C$ 135/night
Cheapest day:Tuesday
Most expensive day:Sunday
C$ 135 - C$ 2,440
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
C$ 176 - C$ 353
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Cheapest vacation rentals in Chicago, Illinois

Discover affordable stays in Chicago that provide a quality experience without breaking the bank. Hotels in Chicago can be found for as low as C$ 128 per night. There is currently one property in Chicago that can be booked for this price. Corporate Suites in the Heart of Magnificent Mile is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 28 March 2024
Currently, these are the lowest-priced vacation rentals in Chicago we've come across for the dates selected. Consider alternative dates if you're able to compare prices.
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Chicago, IL, United States
1.8 km from city centre
Air Conditioning
Free Wi-Fi
C$ 128
Avg. per night
55 East Washington Street, Chicago, IL, United States
0.8 km from city centre
Free Wi-Fi
Airport shuttle
C$ 231
Avg. per night
Chicago, IL, United States
1.2 km from city centre
Air Conditioning
C$ 251
Avg. per night
Chicago, IL, United States
8.6 km from city centre
Air Conditioning
C$ 282
Avg. per night

Vacation rental prices in Chicago

Get a sense of the average price and most popular properties to stay in Chicago to help you budget for your trip accordingly. Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” badge are the most popular hotels in Chicago at attractive prices. Price data was last updated on 28 March 2024.
vacation rentals located in the Chicago area sorted by price and vacation rental class. We've also highlighted the most popular vacation rentals and best value within each vacation rental class.
2 stars
2 stars and under
4 stars
4 stars +
540 North State Street, Chicago, IL, United States
C$ 586

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

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 3,023 hotels in Chicago and price data was last updated on 28 March 2024. The average price for a hotel in Chicago is C$ 418/night.
Show all 3,023 stays
701 North Michigan Avenue, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
C$ 143
Avg. per night
110 West Huron Street, Chicago, IL, United States
2.2 km from city centre
Free Wi-Fi
C$ 188
Avg. per night
1301 North State Parkway, Chicago, IL, United States
3.4 km from city centre
Free Wi-Fi
C$ 188
Avg. per night
24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
C$ 56
Avg. per night
616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
C$ 65
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
C$ 56
Avg. per night

Where to stay in Chicago

Explore different neighbourhoods and areas within Chicago to find the perfect location for your stay. Map data was last updated on 28 March 2024.
Scroll through the map to find vacation rentals close to the Chicago neighborhood(s) you plan on visiting. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

Facts about staying in Chicago

Find useful tips and insights about staying in Chicago to help you make the most of your experience. FAQs were last updated on 28 March 2024.
  • How much does a vacation rental in Chicago cost?

    Chicago vacation rentals are C$ 419/night on average. However, you may find that prices fluctuate depending on the time of year. For example, July is the most expensive month to book a vacation rental in Chicago, and May is often the cheapest month to book. Recently, our users found rentals for C$ 135/night - which is currently the cheapest price. Keep in mind that anything C$ 416/night or less is still considered a good deal.

  • What is the best Chicago vacation rental?

    The Chicago Hotel Collection - Millennium Park has a 3.7 rating from 8 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, 0% 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 3.7/10 review score from 8 users. The distance from Navy Pier to The Chicago Hotel Collection - Millennium Park is 2.0 km.

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