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Vacation rentals in Chicago

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Travel insights for vacation rentals in Chicago

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

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

The cheapest month to book a vacation rental in Chicago is March ($70). Conversely, the most expensive month to stay in Chicago is April ($726).

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

The cheapest day to stay in Chicago is Friday ($198). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $425.

Which Chicago neighborhoods are most popular to stay in?

Those visiting Chicago tend to stay in Pilsen, where a vacation rental costs around $238/night. Another popular neighborhood in Chicago is Lower West Side, which is $232/night on average for a vacation rental.

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

Save money by booking a vacation rental at least 82 days before your trip to Chicago. The lowest price found when booking 82 days ahead was $128 per night.

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Cheapest vacation rentals in Chicago, Illinois

These are the lowest prices we've found on vacation rentals in Chicago at the moment. If you have the flexibility, change the dates selected to compare prices.
The Greenleaf House
The Greenleaf House

The Greenleaf House

1320 West Greenleaf Avenue, Chicago, IL, United States
9.5 mi from city centre
Free Wi-Fi
Air Conditioning
$56
Avg. per night
View deal
Mccormick Place Guest House
Mccormick Place Guest House

Mccormick Place Guest House

Chicago, IL, United States
3.3 mi from city centre
Air Conditioning
Airport shuttle
$119
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
1.2 mi from city centre
Free Wi-Fi
$129
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
1.9 mi from city centre
Free Wi-Fi
$264
Avg. per night
View deal

Other accommodations in Chicago

Chicago Parthenon Hostel
Chicago Parthenon Hostel

Chicago Parthenon Hostel

310 South Halsted Street, Chicago, IL, United States
1.0 mi from city centre
Free Wi-Fi
Air Conditioning
$48
Avg. per night
View deal
HI Chicago Hostel
HI Chicago Hostel

HI Chicago Hostel

24 East Ida B. Wells Drive, Chicago, IL, United States
0.0 mi from city centre
Free Wi-Fi
$56
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
1.0 mi from city centre
Pool
Free Wi-Fi
$154
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
0.8 mi from city centre
Free Wi-Fi
$165
Avg. per night
View deal
Park Hyatt Chicago
Park Hyatt Chicago

Park Hyatt Chicago

800 North Michigan Avenue, Chicago, IL, United States
1.5 mi from city centre
Pool
Free Wi-Fi
$543
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. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chicago

  • How much does a vacation rental in Chicago cost?

    $240 per night is how much a vacation rental in Chicago costs, on average. $16 per night was the cheapest price recently found by our users, though anything for $182 per night or less is a good deal. Keep in mind that Chicago vacation rental prices fluctuate throughout the year: the most expensive month to book is September, and the cheapest time to book is October.

  • What is the best Chicago vacation rental?

    Level Chicago - Old Town has a 9.2 rating from 344 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 12.5 mi 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 Rush University Medical Center?

    If you’re looking for a vacation rental close to Rush University Medical Center while in Chicago, then the most popular is FOUND Hotels, Chicago, Series by Marriott with a 7.8/10 review score from 2,162 users. The distance from Rush University Medical Center to FOUND Hotels, Chicago, Series by Marriott is 2.2 mi.

  • Are there Chicago vacation rentals with “Pool” listed as an amenity?

    1 vacation rental in Chicago currently mentions “Pool” as a listed amenity. We recommend booking the Level Chicago - Old Town, which is the most popular Chicago vacation rental featuring this amenity.

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Consider other places to stay in Chicago

Chicago Bed & Breakfasts
Chicago Inns
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