Holiday Rentals in Chicago, IL

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

Chicago, IL, United States
5 Apr — 6 Apr2
Chicago, IL, United States
Fri 5/4
Sat 6/4
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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 29 March 2024. The average price for a hotel in Chicago is $532/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
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
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

Tips for booking holiday 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 29 March 2024.
Cheapest month:February
Most expensive month:July
Average price in Chicago:$532/night
Cheapest price found:$154/night
Cheapest day:Wednesday
Most expensive day:Friday
$260 - $1,101
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$333 - $933
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

Cheapest holiday 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 $157 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 29 March 2024
Currently, these are the lowest-priced holiday rentals in Chicago we've come across for the dates selected. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Show all 3,023 holiday rentals
Chicago, IL, United States
1.8 km from city centre
Air conditioning
Free Wi-Fi
$157
Avg. per night
55 East Washington Street, Chicago, IL, United States
0.8 km from city centre
Free Wi-Fi
Airport shuttle
$284
Avg. per night
Chicago, IL, United States
1.2 km from city centre
Air conditioning
$309
Avg. per night
Chicago, IL, United States
8.6 km from city centre
Air conditioning
$348
Avg. per night

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 3,023 hotels in Chicago and price data was last updated on 29 March 2024. The average price for a hotel in Chicago is $532/night.
Show all 3,023 stays
24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
$71
Avg. per night
616 West Arlington Place, Chicago, IL, United States
5.8 km from city centre
Free Wi-Fi
$81
Avg. per night
3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
$69
Avg. per night
30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
$263
Avg. per night
1301 North State Parkway, Chicago, IL, United States
3.4 km from city centre
Free Wi-Fi
$233
Avg. per night
122 West Monroe Street, Chicago, IL, United States
0.7 km from city centre
$362
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 29 March 2024.
Utilise the map to find properties close to the Chicago area(s) or attractions you plan on visiting. Users can click on a holiday 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 29 March 2024.
  • How much does a holiday rental in Chicago cost?

    $533/night is a typical cost for a holiday rental in Chicago throughout the year. Rental prices do vary though, and you’ll find that August is the most expensive month to book, and April is the cheapest month to book. HotelsCombined users recently found Chicago holiday rentals for as low as $155/night. In general, any Chicago rental for $487 or less is a good deal.

  • What is the best Chicago holiday rental?

    The Chicago Hotel Collection - Millennium Park is considered the best Chicago holiday rental based on HotelsCombined user data. The Chicago Hotel Collection - Millennium Park has an average rating of 3.8/10 and 7 reviews.

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

    It’s only 25.4 km from Chicago O'Hare Intl Airport to The Chicago Hotel Collection - Millennium Park (the nearest Chicago holiday rental to the airport).

  • What part of Chicago is best to stay in?

    Downtown is the most popular area of Chicago to stay in. In the past year, 20% of HotelsCombined users looking for Chicago holiday rentals searched within Downtown. Based on user data, the 4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena is one of the most popular holiday rentals in Downtown.

  • What’s the most popular holiday rental in Chicago near Union Station?

    With a score of 3.8/10 from 7 reviews, The Chicago Hotel Collection - Millennium Park is the most popular holiday rental in Chicago that’s close to Union Station (just 1.3 km away).

  • Are there any Motel holiday rentals in Chicago?

    At the moment, there are 34 properties listed as a Motel holiday rental in Chicago. A popular Motel in Chicago amongst our users is Motel 6 Elk Grove Village - O'Hare.

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