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Vacation rentals in Chicago

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Travel insights for holiday rentals in Chicago

Use these up-to-date, data-driven insights about booking a holiday rental in Chicago including ideal times to book, pricing trends, and more.

What is the cheapest month to book a vacation rental in Chicago?

The cheapest month to book a vacation rental in Chicago is January (₹ 10,474). Conversely, the most expensive month to stay in Chicago is February (₹ 144,299).

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

The cheapest day to stay in Chicago is Monday (₹ 15,210). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is ₹ 43,104.

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

Save money by booking a vacation rental at least 79 days before your trip to Chicago. The lowest price found when booking 79 days ahead was ₹ 12,944 per night.

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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 ₹ 16,982 per night. There is currently one property in Chicago that can be booked for this price. Level Chicago - Old Town is one of the hotels that can be booked for the lowest price in Chicago. Price data was last updated on 11 December 2025
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.
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
₹ 16,982
Avg. per night
View Deal
Just Minutes from Downtown Chicago
Just Minutes from Downtown Chicago

Just Minutes from Downtown Chicago

Chicago, IL, United States
7.2 km from city centre
Air conditioning
₹ 18,426
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect holiday rental for your stay in Chicago. There are 2,506 hotels in Chicago and price data was last updated on 11 December 2025. The average price for a hotel in Chicago is ₹ 30,737/night.
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
₹ 4,674
Avg. per night
View Deal
Wrigley Hostel - Chicago
Wrigley Hostel - Chicago

Wrigley Hostel - Chicago

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
₹ 3,781
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 11 December 2025.
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 11 December 2025.

  • How much does a holiday rental in Chicago cost?

    A holiday rental in Chicago will cost ₹ 30,738 per night on average. However some users found rentals for as low as ₹ 1,026 per night. A good deal on a Chicago holiday rental would be anything for ₹ 16,582 per night or less. Keep in mind that booking February may be more expensive, whereas booking December 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 8.2/10 and 1,108 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 part of Chicago is best to stay in?

    Downtown is the best part of the city to stay in if you’re looking for a holiday rental in Chicago. The 23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown is our most popular holiday rental in this neighbourhood. While there are other neighbourhoods throughout Chicago, 2% of HotelsCombined users searched for rentals in Downtown in the past 12 months, making it a popular choice.

  • 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 8.2/10 from 1,108 HotelsCombined users and it’s located just 0.2 km from Magnificent Mile.

  • Are there any Motel holiday rentals in Chicago?

    34 Motel holiday rentals are available in Chicago. Based on our user data, the most popular is Ohio House Motel - so we recommend seeing if this property is available for your travel dates before looking at other Motel options in Chicago.

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