Insights
Cheapest hotels
Where to stay

Vacation rentals in Chicago

Search and compare Chicago, IL holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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 Sunday (₹ 17,761). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is ₹ 47,500.

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

Save money by booking a vacation rental at least 72 days before your trip to Chicago. The lowest price found when booking 72 days ahead was ₹ 3,759 per night.

Find deals

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 ₹ 7,615 per night. There is currently one property in Chicago that can be booked for this price. The Greenleaf House is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 27 July 2026
For those on a budget, these are the cheapest vacation rentals available in Chicago for the selected dates. 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
₹ 7,615
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
₹ 21,019
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
₹ 27,110
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,565 hotels in Chicago and price data was last updated on 27 July 2026. The average price for a hotel in Chicago is .
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
₹ 27,672
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
₹ 24,848
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
₹ 63,416
Avg. per night
View Deal
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
₹ 6,556
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
₹ 6,363
Avg. per night
View Deal

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 27 July 2026.
Navigate to the areas in Chicago you plan to visit to find vacation rentals that are close by. You can find more information on a particular vacation rental within the map by clicking on its name.

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 27 July 2026.

  • How much does a holiday rental in Chicago cost?

    A holiday rental in Chicago will cost ₹ 23,585 per night on average. However some users found rentals for as low as ₹ 1,100 per night. A good deal on a Chicago holiday rental would be anything for ₹ 17,196 per night or less. Keep in mind that booking August may be more expensive, whereas booking August is the cheapest month of the year to book.

  • What is the best Chicago holiday rental?

    Hotel 55 Chicago Downtown is considered the best Chicago holiday rental based on HotelsCombined user data. Hotel 55 Chicago Downtown has an average rating of 8.3/10 and 1,117 reviews.

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

    The Greenleaf House is the closest Chicago holiday rental to Chicago O'Hare Intl Airport at a distance of 20.2 km.

  • What’s the most popular holiday rental in Chicago near Magnificent Mile?

    The most popular holiday rental near Chicago’s Magnificent Mile is Hotel 55 Chicago Downtown. Hotel 55 Chicago Downtown has a review score of 8.3/10 from 1,117 HotelsCombined users and it’s located just 0.2 km from Magnificent Mile.

See more FAQs

Find better results for your stay in Chicago

Consider other places to stay in Chicago

Stay at one of these places that users have found on HotelsCombined.
Chicago Inns