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Hotels in Chicago

Vacation rentals in Chicago, IL

Find deals on vacation rentals in Chicago, IL

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Top rentals in Chicago

Find the perfect vacation rental for your stay in Chicago
Price
C$ 68
C$ 797
Review Score
0+
6+
7+
8+
9+

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
Lincoln Park
Search rentals in Lincoln Park
Lincoln Park Living - 3 Queen Beds - Sleeps 6 Photo
Best value

Lincoln Park Living - 3 Queen Beds - Sleeps 6

1147 West Diversey Parkway, Chicago, IL, United States

9.2
C$ 144
View Deal
#1 Most popular

Entire Apartment in Heart of Lincoln Par

Chicago, IL, United States

4.8
C$ 754
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#2 Most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.1
C$ 387
View Deal
Charming & Bright Multilevel Townhome with Parking Photo
#3 Most popular

Charming & Bright Multilevel Townhome with Parking

Chicago, IL, United States

8.0
C$ 509
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Hyde Park
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Best value

Hyde Park Shared Apartments

Chicago, IL, United States

5.6
C$ 158
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Cozy Studio in Hyde Park-Walk to Lake & University Photo
#1 Most popular

Cozy Studio in Hyde Park-Walk to Lake & University

Chicago, IL, United States

8.2
C$ 187
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#2 Most popular

Lively 1br - Kenwood 408

Chicago, IL, United States

C$ 304
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#3 Most popular

Cozy Studio in Hyde Park - BS 226 rep

Chicago, IL, United States

5.0
C$ 312
View Deal
Near South Side
Search rentals in Near South Side
Luxury Studio Apartment with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field Photo
Best value

Luxury Studio Apartment with Optional Parking and Gym Access Near McCormick Place, Chinatown and Soldier Field

Chicago, IL, United States

8.7
C$ 188
View Deal
#1 Most popular

Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena

Chicago, IL, United States

8.8
C$ 563
View Deal
South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field Photo
#2 Most popular

South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field

Chicago, IL, United States

7.5
C$ 232
View Deal
Mccormick Place Modern And Cosy 420 Frie Photo
#3 Most popular

Mccormick Place Modern And Cosy 420 Frie

2112 South Michigan Avenue Unit 2, Chicago, IL, United States

6.9
C$ 650
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#4 Most popular

McCormick Place Modern 2BR Loft in Downtown Chicago Michigan Avenue with Optional Parking Near Soldier Field

Chicago, IL, United States

9.5
C$ 225
View Deal
North Center
Search rentals in North Center
Best value

The Lyons' Den

Chicago, IL, United States

9.4
C$ 206
View Deal
#1 Most popular

Lyons' Suite

Chicago, IL, United States

9.5
C$ 626
View Deal
The Lyons' Lair Photo
#2 Most popular

The Lyons' Lair

Chicago, IL, United States

9.6
C$ 264
View Deal
#3 Most popular

3BR Comfy & Bright Apt in North Center

Chicago, IL, United States

7.7
C$ 709
View Deal

Hostels and cheap hotels in Chicago

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

Homestay - family in chicago

Chicago, IL, United States

C$ 46
View Deal
1071913881

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

C$ 64
View Deal
1070239888

Homestay - Chicago, Home of Presidents!

Chicago, IL, United States

C$ 49
View Deal
10379428

Homestay - Friendly Homestay

Chicago, IL, United States

C$ 64
View Deal
10379883

Homestay - The Lake House

Chicago, IL, United States

C$ 64
View Deal
1070239309

Homestay - Close to lake and transportation

Chicago, IL, United States

C$ 69
View Deal
11179024

Get the best value vacation rental in Chicago

These Chicago vacation rentals have the best prices for their ratings
Pulaski Point Properties Photo

Pulaski Point Properties

3936 North Pulaski Road, Chicago, IL, United States

9.7
C$ 220
View Deal
1071986668
Private Basement Suite-Completely separate from the rest of the house Photo

Private Basement Suite-Completely separate from the rest of the house

Chicago, IL, United States

10.0
C$ 140
View Deal
11343816
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.2
C$ 230
View Deal
7682996
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.7
C$ 146
View Deal
1072424431
Sonder The Burnham Photo

Sonder The Burnham

555 West Jackson Boulevard, Chicago, IL, United States

7.9
C$ 181
View Deal
10190685
Level Chicago - Fulton Market Photo

Level Chicago - Fulton Market

354 North Union Avenue, Chicago, IL, United States

7.1
C$ 235
View Deal
9474213

momondo's favourite vacation rentals in Chicago

Learn more about these user-preferred vacation rentals in Chicago

Lyons' Suite

Chicago, IL, United States

9.5
C$ 626
Pulaski Point Properties Photo

Pulaski Point Properties

3936 North Pulaski Road, Chicago, IL, United States

9.7
C$ 220
Livn Millennium Park Downtown Chicago Studio Photo

Livn Millennium Park Downtown Chicago Studio

Chicago, IL, United States

8.7
C$ 324

Super Amazing Place To Stay Near Downtown! Free Parking

Chicago, IL, United States

8.0
C$ 671

Homestay - Fun family that loves the outdoors.

Chicago, IL, United States

C$ 102

Homestay - Chicago, Home of Presidents!

Chicago, IL, United States

C$ 49
Relaxing Chicago Studio Photo

Relaxing Chicago Studio

Chicago, IL, United States

9.8
C$ 175

Indoor Pool Gym Rooftop-215-by Cloud9

215 West Lake Street, Chicago, IL, United States

8.3
C$ 608
747 Lofts by RedAwning - River West, Second Floor Chicago Photo

747 Lofts by RedAwning - River West, Second Floor Chicago

747 N May St., Chicago, IL, United States

7.8
C$ 199
Iconic Downtown Penthouses Getaway + City Views Photo

Iconic Downtown Penthouses Getaway + City Views

Chicago, IL, United States

9.0
C$ 4,402
Cozy Spacious Garden Unit Photo

Cozy Spacious Garden Unit

Chicago, IL, United States

C$ 200
Livn West Loop Chicago 2 Br City View Photo

Livn West Loop Chicago 2 Br City View

Chicago, IL, United States

9.1
C$ 345

Entire Modern 2 Bedroom Apartment

Chicago, IL, United States

7.8
C$ 263

Luxery Stay Chicago - Themed Units! Close To Downtown, Mccormick Place & Wintrust Arena

Chicago, IL, United States

8.8
C$ 563

Homestay - The Lake House

Chicago, IL, United States

C$ 64
Fulbrix Bright Designer Apartments with West Loop Views Photo

Fulbrix Bright Designer Apartments with West Loop Views

Chicago, IL, United States

9.1
C$ 730
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym Photo

Regal Stylish Uptown Loft Beachfront Rooftopwfhgym

Chicago, IL, United States

9.3
C$ 153
Chic 1-bedroom apartment in fantastic Chicago with WiFi, AC Photo

Chic 1-bedroom apartment in fantastic Chicago with WiFi, AC

Chicago, IL, United States

C$ 120
South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field Photo

South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field

Chicago, IL, United States

7.5
C$ 232

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

C$ 64

Useful insights on Chicago vacation rentals

Get a quick overview on price and accommodation trends for your visit in Chicago

Average Length of Stay

3 days
On average, people stay for 3 days when lodging at vacation rentals in Chicago. The average accommodation price for 3 days in Chicago in the past week is C$ 1,177.

When to book a vacation rental in Chicago

Check out the information below to find the best deal on a vacation rental in Chicago
Cheapest day of weekWednesdayis the cheapest day of the week to book
Highest day of weekTuesdayis the most expensive day of the week to book
C$ 333is the average per night cost for a vacation rental on this day
C$ 498is the average per night cost for a vacation rental on this day

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$ 361 - C$ 443

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side13% cheaperVacation rentals in Near North Side are the cheapest in Chicago at just C$ 361 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGOLoop6% more expensiveLoop has the highest priced vacation rentals in Chicago with properties averaging C$ 443 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGOLoop29% more users visitedMore momondo users search for vacation rentals in Loop than any other neighbourhood in Chicago

Information about staying in Chicago

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

How long do people typically book vacation apartments for in Chicago?

On average, people book vacation rentals in Chicago for stays of around 3 nights.

How much does a vacation rental apartment in Chicago cost?

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$ 348 per night.

When is the best time to book a vacation rental in Chicago?

Vacation apartments in Chicago are often cheapest in February - rental prices can be around 58% lower than the average during this period.

What’s the best area of Chicago to book a vacation rental in?

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

How many operators does momondo search for hotels in Chicago?

There are 2,658 operators available for hotels in Chicago as of October 2026.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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