Vacation rentals in Chicago, IL

Find deals on 2,152 vacation rentals in Chicago, IL

Chicago, IL
May 26 — May 272
Chicago, IL
Thu 5/26
Fri 5/27

Top rentals in Chicago

Find the perfect vacation rental for your stay in Chicago
Price
$10
$513.59
Review Score
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Hotel class
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Best neighborhoods to book a vacation rental in Chicago

Below are the average prices for vacation rentals in the most popular neighborhoods in Chicago

Price

$126 - $282

CHEAPEST NEIGHBORHOOD IN CHICAGONear West Side31% cheaperVacation rentals in Near West Side are the cheapest in Chicago at just $126 per night on average
MOST EXPENSIVE NEIGHBORHOOD IN CHICAGOLoop36% more expensiveLoop has the highest priced vacation rentals in Chicago with properties averaging $282 per night
MOST POPULAR NEIGHBORHOOD IN CHICAGONear North Side46% more users visitedMore momondo users search for vacation rentals in Near North Side than any other neighborhood in Chicago

Vacation rentals in popular neighborhoods in Chicago

Below are the most popular neighborhoods in Chicago to stay in, as well as some of the best vacation rentals in each area

When to book a vacation rental in Chicago

Check out the information below to find the best deal on a vacation rental in Chicago
Low SeasonJanuarycheapest month to stay
High SeasonMarchmost expensive time to stay
39%expected price decrease
45%expected price increase

Price

$146 - $431

Highest day of weekFridayis the most expensive day of the week to book
Cheapest day of weekMondayis the cheapest day of the week to book
$261
$180

Hostels and cheap hotels in Chicago

These hotels and hostels usually make for a cheap way to stay in Chicago

Get the best value vacation rental in Chicago

These Chicago vacation rentals have the best prices for their ratings

Information about staying in Chicago

Read these important travel tips before booking a vacation rental in Chicago

The average length of a vacation rental booking in Chicago is 2 nights.

The cheapest month to rent a vacation apartment in Chicago is usually January. The cost of your apartment or rental property can be around 39% cheaper in January vs. the high season.

Hyde Park is the most popular area of Chicago to book a rental apartment in. Lincoln Park and Logan Square are also sought-after places to stay.


momondo's favorite vacation rentals in Chicago

Learn more about these user-preferred vacation rentals in Chicago

Unique 2BR in South Loop by Sonder

Chicago, IL, United States

$221

Stunning 2br In Wrigleyville By Sonder

North Southport Avenue And Waveland, Chicago, IL, United States

$121

Sonder - Lincoln Park Zoo

Chicago, IL, United States

9.2
$41

Sonder - Wrightwood Park

Chicago, IL, United States

$171

Gorgeous 2br/2ba Penthouse In Loop High Rise

Chicago, IL, United States

9.7
$414

Aqua Chicago

225 North Columbus Drive, Chicago, IL, United States

$96
Gold Coast Historic Living-Private Room In A House

Gold Coast Historic Living-Private Room In A House

Chicago, IL, United States

7.2
$196

Sonder South State Unique 2Br + Fitness Room

Chicago, IL, United States

$202

Bright 1BR in the South Loop by Sonder

Chicago, IL, United States

$151

Sonder - Six Points - Sunny 1Br

Chicago, IL, United States

9.2
$125
New! Smart 2BR Near Mccormick Place by Domio

New! Smart 2BR Near Mccormick Place by Domio

Chicago, IL, United States

$192

Incredible West Loop Suites by Sonder

Chicago, IL, United States

$165
Chicago Guest House on Henderson Street

Chicago Guest House on Henderson Street

1330 W Henderson Street, Chicago, IL, United States

$428
Gold Coast Luxury Living-private room in a house

Gold Coast Luxury Living-private room in a house

Chicago, IL, United States

10.0
$175

Cozy Garden 2 bedroom-Near United Center

Chicago, IL, United States

$506

Sonder - Six Points - Sunny 1br

Chicago, IL, United States

$135

Panoramic 2BR near Restaurant Row by Sonder

Chicago, IL, United States

$212
Light-Filled Chicago Charmer In Wicker Park

Light-Filled Chicago Charmer In Wicker Park

Chicago, IL, United States

8.6
$84

Entire 2br

Chicago, IL, United States

9.5
$270

Walk To Everythingbeautiful City Viewsshedd Aquariummillennium Park

Chicago, IL, United States

$359

Start planning your trip to Chicago


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