Vacation rentals in Chicago, IL

Find deals on 2,154 vacation rentals in Chicago, IL

Chicago, IL, United States
18 May — 19 May2
Chicago, IL, United States
Wed 18/5
Thu 19/5

Top rentals in Chicago

Find the perfect vacation rental for your stay in Chicago
Price
C$12.91
C$595.05
Review Score
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Hotel class
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Best neighbourhoods to book a vacation rental in Chicago

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

Price

C$ 162 - C$ 364

CHEAPEST NEIGHBOURHOOD IN CHICAGONear West Side31% cheaperVacation rentals in Near West Side are the cheapest in Chicago at just C$ 162 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGOLoop36% more expensiveLoop has the highest priced vacation rentals in Chicago with properties averaging C$ 364 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side46% more users visitedMore momondo users search for vacation rentals in Near North Side than any other neighbourhood in Chicago

Vacation rentals in popular neighbourhoods in Chicago

Below are the most popular neighbourhoods 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
29%expected price decrease
24%expected price increase

Price

C$ 196 - C$ 366

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
C$ 434
C$ 301

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

On average, people book vacation rentals in Chicago for stays of around 2 nights.

The price of a vacation apartment in Chicago depends on the number of guests, locations and required amenities - for a standard apartment in Chicago you can expect to pay around C$ 655 per night.

Vacation apartments in Chicago are often cheapest in January - rental prices can be around 30% lower than the average during this period.

Logan Square is the most popular area of Chicago to book a rental apartment in. Near North Side and Grand Boulevard are also sought-after places to stay.


momondo's favourite 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

C$ 285

Stunning 2br In Wrigleyville By Sonder

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

C$ 156

Sonder - Lincoln Park Zoo

Chicago, IL, United States

9.2
C$ 53

Sonder - Wrightwood Park

Chicago, IL, United States

C$ 221

Gorgeous 2br/2ba Penthouse In Loop High Rise

Chicago, IL, United States

9.7
C$ 534

Aqua Chicago

225 North Columbus Drive, Chicago, IL, United States

C$ 124
Gold Coast Historic Living-Private Room In A House

Gold Coast Historic Living-Private Room In A House

Chicago, IL, United States

7.2
C$ 253

Sonder South State Unique 2Br + Fitness Room

Chicago, IL, United States

C$ 261

Bright 1BR in the South Loop by Sonder

Chicago, IL, United States

C$ 195

Sonder - Six Points - Sunny 1Br

Chicago, IL, United States

9.2
C$ 161
New! Smart 2BR Near Mccormick Place by Domio

New! Smart 2BR Near Mccormick Place by Domio

Chicago, IL, United States

C$ 248

Incredible West Loop Suites by Sonder

Chicago, IL, United States

C$ 213
Chicago Guest House on Henderson Street

Chicago Guest House on Henderson Street

1330 W Henderson Street, Chicago, IL, United States

C$ 508
Gold Coast Luxury Living-private room in a house

Gold Coast Luxury Living-private room in a house

Chicago, IL, United States

10.0
C$ 226

Cozy Garden 2 bedroom-Near United Center

Chicago, IL, United States

C$ 653

Sonder - Six Points - Sunny 1br

Chicago, IL, United States

C$ 174

Panoramic 2BR near Restaurant Row by Sonder

Chicago, IL, United States

C$ 274
Light-Filled Chicago Charmer In Wicker Park

Light-Filled Chicago Charmer In Wicker Park

Chicago, IL, United States

8.6
C$ 56

Entire 2br

Chicago, IL, United States

9.5
C$ 55

Walk To Everythingbeautiful City Viewsshedd Aquariummillennium Park

Chicago, IL, United States

C$ 463

Start planning your trip to Chicago


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