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Vacation rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Chicago.

What is the cheapest day to stay in a vacation rental in Chicago?

The cheapest day to stay in Chicago is Saturday (S$ 328). On the other hand, travellers can expect to pay the most on Thursday, when the average nightly price is S$ 634.

How far ahead should you book a vacation rental in Chicago?

Save money by booking a vacation rental at least 50 days before your trip to Chicago. The lowest price found when booking 50 days ahead was S$ 210 per night.

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Cheapest holiday rentals in Chicago, Illinois

Out of the vacation rentals in Chicago we've come across, these properties are priced the lowest. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
The Greenleaf House
The Greenleaf House

The Greenleaf House

1320 West Greenleaf Avenue, Chicago, IL, United States
15.3 km from city centre
Free Wi-Fi
Air conditioning
S$ 80
Avg. per night
View Deal
FOUND Hotels, Chicago, Series by Marriott
FOUND Hotels, Chicago, Series by Marriott

FOUND Hotels, Chicago, Series by Marriott

613 North Wells Street, Chicago, IL, United States
2.0 km from city centre
Free Wi-Fi
S$ 197
Avg. per night
View Deal
Level Chicago - Old Town
Level Chicago - Old Town

Level Chicago - Old Town

1140 North Wells Street, Chicago, IL, United States
3.1 km from city centre
Free Wi-Fi
S$ 351
Avg. per night
View Deal

Other accommodation in Chicago

Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
1.7 km from city centre
Free Wi-Fi
Air conditioning
S$ 66
Avg. per night
View Deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.1 km from city centre
Free Wi-Fi
S$ 82
Avg. per night
View Deal
Courtyard by Marriott Chicago Downtown/River North
Courtyard by Marriott Chicago Downtown/River North

Courtyard by Marriott Chicago Downtown/River North

30 East Hubbard Street, Chicago, IL, United States
1.6 km from city centre
Pool
Free Wi-Fi
S$ 277
Avg. per night
View Deal
L7 Chicago by LOTTE
L7 Chicago by LOTTE

L7 Chicago by LOTTE

225 North Wabash Avenue, Chicago, IL, United States
1.2 km from city centre
Free Wi-Fi
S$ 276
Avg. per night
View Deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
2.4 km from city centre
Pool
Free Wi-Fi
S$ 740
Avg. per night
View Deal

Where to stay in Chicago

Use the map to find vacation rentals in Chicago that are close to the points of interest you'll be frequenting. More information on a given vacation rental can be accessed by clicking the vacation rental's name within the map.

Facts about staying in Chicago

  • How much does a holiday rental in Chicago cost?

    On average, it costs S$ 320 per night for a Chicago holiday rental, but S$ 261 per night or less would be considered a good deal. The cheapest holiday rental price our users have found recently in Chicago was for S$ 37 per night. If you can, try to avoid booking your rental September (as this is the most expensive month). Booking July (the cheapest month) may end up saving you money.

  • What is the best Chicago holiday rental?

    While there may be other great holiday rentals in Chicago to choose from, Hotel 55 Chicago Downtown is currently considered the best, based on 1,123 HotelsCombined reviews and an average rating of 8.3/10.

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

    If you’re looking to stay close to Chicago O'Hare Intl Airport for your trip to Chicago, then consider booking a The Greenleaf House holiday rental. This holiday apartment is just 20.2 km away from the Chicago airport.

  • What’s the most popular holiday rental in Chicago near Grant Park?

    The most popular holiday rental near Chicago’s Grant Park is Hotel 55 Chicago Downtown. Hotel 55 Chicago Downtown has a review score of 8.3/10 from 1,123 HotelsCombined users and it’s located just 2.0 km from Grant Park.

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