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Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on holiday rentals in Chicago, IL

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Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
Price
₹ 4,452
₹ 43,340
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
O'Hare
Search rentals in O'Hare
Best value

Luxury Studio King Bed Chicago Remodeled

Chicago, IL, United States

10.0
₹ 7,723
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No. 1 most popular

Luxurious New Remodeled

Chicago, IL, United States

8.8
₹ 20,716
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No. 2 most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
₹ 10,321
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No. 3 most popular

Luxurious Condo In Top Rated Neighborhoo

Chicago, IL, United States

1.0
₹ 14,992
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Lincoln Park
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Historic Old Town One Bedroom Suite Photo
Best value

Historic Old Town One Bedroom Suite

Chicago, IL, United States

₹ 9,994
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Lincoln Park Living - Suite 2! Photo
No. 1 most popular

Lincoln Park Living - Suite 2!

1147 W Diversey Pkwy, Chicago, IL, United States

9.3
₹ 12,839
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Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover Photo
No. 2 most popular

Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover

Chicago, IL, United States

9.3
₹ 13,992
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Entire Building-Walk To Lincoln Park Or The Beach! Photo
No. 3 most popular

Entire Building-Walk To Lincoln Park Or The Beach!

1147 W Diversey Pkwy, Chicago, IL, United States

9.4
₹ 38,978
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No. 4 most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.1
₹ 11,867
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Near North Side
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Brownstone in Gold Coast - Downtown Photo
Best value

Brownstone in Gold Coast - Downtown

Chicago, IL, United States

9.3
₹ 8,995
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Chic River North Retreat Photo
No. 1 most popular

Chic River North Retreat

Chicago, IL, United States

7.9
₹ 22,260
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Kasa River North Chicago Photo
No. 2 most popular

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
₹ 10,092
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No. 3 most popular

Aurelien Spacious Apartments in the Heart of Gold Coast

Chicago, IL, United States

8.9
₹ 28,034
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51/52nd Floor Penthouse-Views, Fireplace, Pool Photo
No. 4 most popular

51/52nd Floor Penthouse-Views, Fireplace, Pool

Chicago, IL, United States

9.7
₹ 48,700
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Rogers Park
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Cozy Private Room in Chicago, Queen Bed, Up to 5 People, Free Parking, 32+ Stay Photo
Best value

Cozy Private Room in Chicago, Queen Bed, Up to 5 People, Free Parking, 32+ Stay

Chicago, IL, United States

₹ 5,906
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No. 1 most popular

The Greenleaf House

Chicago, IL, United States

8.3
₹ 7,905
View Deal
Sunlit Studio with City Charm Photo
No. 2 most popular

Sunlit Studio with City Charm

Chicago, IL, United States

7.8
₹ 8,363
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Cozy apartment with AC and WiFi in awesome Chicago Photo
No. 3 most popular

Cozy apartment with AC and WiFi in awesome Chicago

Chicago, IL, United States

9.3
₹ 10,432
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Urban Chicago Vacation Rental Condo Near Beach! Photo
No. 4 most popular

Urban Chicago Vacation Rental Condo Near Beach!

Chicago, IL, United States

9.3
₹ 13,851
View Deal

Hostels and cheap hotels in Chicago

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

Homestay - Cozy Room Near All Universities

Chicago, IL, United States

₹ 3,271
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Homestay - The Lake House

Chicago, IL, United States

₹ 4,179
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Homestay - Convenient Room w/Private Bathroom

Chicago, IL, United States

₹ 3,362
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Homestay - Charming home in quite neighborhood

Chicago, IL, United States

₹ 4,179
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Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

₹ 3,998
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Homestay - Family close to transportation

Chicago, IL, United States

₹ 4,452
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Get the best value holiday rental in Chicago

These Chicago holiday rentals have the best prices for their ratings
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
₹ 10,092
View Deal
Level Chicago - Fulton Market Photo

Level Chicago - Fulton Market

354 North Union Avenue, Chicago, IL, United States

7.3
₹ 15,329
View Deal
Dorothy's Photo

Dorothy's

3445 North Halsted Street, Chicago, IL, United States

7.5
₹ 4,997
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A laid-back studio few minutes from Wrigley Field Photo

A laid-back studio few minutes from Wrigley Field

Chicago, IL, United States

9.1
₹ 8,632
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Pulaski Point Properties Photo

Pulaski Point Properties

Chicago, IL, United States

9.6
₹ 8,993
View Deal
Modern and Comfy 1BR Apartment in Logan Square! Photo

Modern and Comfy 1BR Apartment in Logan Square!

Chicago, IL, United States

9.4
₹ 9,226
View Deal

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
₹ 10,540

Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

₹ 3,998
Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop Photo

Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop

Chicago, IL, United States

8.5
₹ 24,049

Super Amazing Place To Stay Near Downtown! Free Parking

Chicago, IL, United States

7.3
₹ 4,906
Chic River North Retreat Photo

Chic River North Retreat

Chicago, IL, United States

7.9
₹ 22,260

Homestay - The Lake House

Chicago, IL, United States

₹ 4,179

Homestay - Friendly Family in Chicago

Chicago, IL, United States

₹ 5,088

Hyde Park Modern Private Room - Near Univ of Chicago

4808 South Drexel Boulevard Unit #E, Chicago, IL, United States

7.4
₹ 9,449
Premier Penthouses and Apartment with Captivating Views of Millennium Park Photo

Premier Penthouses and Apartment with Captivating Views of Millennium Park

Chicago, IL, United States

9.5
₹ 39,908

A Hidden Gem, approx 15 mins to downtown Chicago!

Chicago, IL, United States

8.5
₹ 8,450

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
₹ 10,321

Amazing Place to stay near Downtown Chicago!

Chicago, IL, United States

8.8
₹ 4,906
The Neighborhood Hotel - Little Italy Two Bedroom - Ada Photo

The Neighborhood Hotel - Little Italy Two Bedroom - Ada

Chicago, IL, United States

9.1
₹ 16,082
1 Bedroom with Rooftop and Wrigley Views Photo

1 Bedroom with Rooftop and Wrigley Views

Chicago, IL, United States

9.0
₹ 15,490
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
₹ 10,092
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.9
₹ 14,901

Beautiful 4 bedroom 2 bathroom apartment near everything

Chicago, IL, United States

7.6
₹ 17,263

The Lyons' Den

Chicago, IL, United States

9.7
₹ 11,630

Lux Apts with Lake Views and Top Amenities

Chicago, IL, United States

9.9
₹ 32,737
Chic Chicago Retreat (2-Bedroom Home) by RedAwning Photo

Chic Chicago Retreat (2-Bedroom Home) by RedAwning

Chicago, IL, United States

7.6
₹ 13,170

When to book a holiday rental in Chicago

Check out the information below to find the best deal on a holiday rental in Chicago
Low seasonFebruarycheapest month to stay
High seasonJunemost expensive time to stay
52%expected price decrease
40%expected price increase

Price

₹ 11,457 - ₹ 39,995

Cheapest day of weekSundayis the cheapest day of the week to book
Highest day of weekTuesdayis the most expensive day of the week to book
₹ 15,557
₹ 68,295

Information about staying in Chicago

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

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

4 nights is the typical length of a Chicago holiday rental booking.

How much does a holiday rental apartment in Chicago cost?

A holiday rental in Chicago will generally cost around ₹ 13,899 per night. This figure is taken from average apartment rental searches in Chicago and prices will vary according to the required size, facilities, and location of the rental.

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

The cheapest month to rent a holiday apartment in Chicago is usually February. The cost of your apartment or rental property can be around 53% cheaper in February vs. the high season.

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

The most popular areas to book Chicago holiday rentals in are Lincoln Park, West Town, and Kenwood.

How many operators does momondo search for hotels in Chicago?

As of January 2026, there are 2,418 operators available to choose from for hotels in Chicago.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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