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Vacation rentals in Chicago

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Travel insights for vacation rentals in Chicago

Use these up-to-date, data-driven insights about booking a vacation 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 November (C$ 190). Conversely, the most expensive month to stay in Chicago is June (C$ 599).

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

The cheapest day to stay in Chicago is Sunday (C$ 240). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is C$ 689.

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 C$ 197 per night.

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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$ 227 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 5 February 2026
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.
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
C$ 227
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
C$ 277
Avg. per night
View Deal

Other accommodations in Chicago

Find the perfect vacation rental for your stay in Chicago. There are 2,718 hotels in Chicago and price data was last updated on 5 February 2026. The average price for a hotel in Chicago is C$ 328/night.
Rodeway Inn Chicago North Shore - Lincolnwood
Rodeway Inn Chicago North Shore - Lincolnwood

Rodeway Inn Chicago North Shore - Lincolnwood

5952 North Lincoln Avenue, Chicago, IL, United States
14.2 km from city centre
Free Wi-Fi
Air Conditioning
Parking
C$ 101
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
C$ 62
Avg. per night
View Deal
Wrigley Hostel
Wrigley Hostel

Wrigley Hostel

3514 North Sheffield Avenue, Chicago, IL, United States
8.1 km from city centre
Free Wi-Fi
Parking
C$ 55
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 5 February 2026.
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 5 February 2026.

  • How much does a vacation rental in Chicago cost?

    Chicago vacation rentals are C$ 329/night on average. However, you may find that prices fluctuate depending on the time of year. For example, December is the most expensive month to book a vacation rental in Chicago, and January is often the cheapest month to book. Recently, our users found rentals for C$ 9/night - which is currently the cheapest price. Keep in mind that anything C$ 228/night or less is still considered a good deal.

  • What is the best Chicago vacation rental?

    Hotel 55 Chicago Downtown has a 8.3 rating from 1,112 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 20.2 km from Chicago O'Hare Intl Airport to The Greenleaf House (the nearest Chicago vacation rental to the airport).

  • What’s the most popular vacation rental in Chicago near Coast at Lakeshore East?

    If you’re looking for a vacation rental close to Coast at Lakeshore East while in Chicago, then the most popular is Hotel 55 Chicago Downtown with a 8.3/10 review score from 1,112 users. The distance from Coast at Lakeshore East to Hotel 55 Chicago Downtown is 0.9 km.

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