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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
₹ 4,443
₹ 34,533
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
Best value

Entire Apartment In Heart Of Lincoln Par

Chicago, IL, United States

10.0
₹ 9,814
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Lincoln Park Living - 3 Queen Beds - Sleeps 6! Photo
No. 1 most popular

Lincoln Park Living - 3 Queen Beds - Sleeps 6!

1147 W Diversey Pkwy, Chicago, IL, United States

9.3
₹ 12,035
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Entire Building-Walk To Lincoln Park Or The Beach! Photo
No. 2 most popular

Entire Building-Walk To Lincoln Park Or The Beach!

1147 W Diversey Pkwy, Chicago, IL, United States

9.4
₹ 67,491
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No. 3 most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.1
₹ 17,498
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Charming & Bright Multilevel Townhome with Parking Photo
No. 4 most popular

Charming & Bright Multilevel Townhome with Parking

Chicago, IL, United States

8.0
₹ 23,330
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O'Hare
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Entire Apartment with Complete Privacy Near O'hare Photo
Best value

Entire Apartment with Complete Privacy Near O'hare

Chicago, IL, United States

1.0
₹ 18,146
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No. 1 most popular

Luxurious New Remodeled

Chicago, IL, United States

8.8
₹ 21,108
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No. 2 most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
₹ 19,534
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Hyde Park
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Best value

Smart Stay In Hyde Park 1br - Bs 908

Chicago, IL, United States

8.0
₹ 9,741
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No. 1 most popular

Hyde Park Shared Apartments

Chicago, IL, United States

5.7
₹ 11,202
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Modern Studio Unit Near Uchicago Photo
No. 2 most popular

Modern Studio Unit Near Uchicago

Chicago, IL, United States

9.8
₹ 15,857
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No. 3 most popular

Lively & Fully Furnished 1br Apartment - Kenwood 408

Chicago, IL, United States

10.0
₹ 12,211
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No. 4 most popular

Sleek 1-Bedroom Apt in Chicago - East Park Tower 0610 rep

Chicago, IL, United States

8.8
₹ 13,785
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Near South Side
Search rentals in Near South Side
South Loop 3 Bedroom Apt Photo
Best value

South Loop 3 Bedroom Apt

Chicago, IL, United States

8.5
₹ 12,591
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No. 1 most popular

Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena

Chicago, IL, United States

8.9
₹ 23,515
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No. 2 most popular

Convenient Cozy 2BR Loft with Optional Parking for 8 guests Near McCormick Place, Soldier Field and Lakefront Trail

Chicago, IL, United States

7.9
₹ 17,126
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No. 3 most popular

Mccormick 2b 2ba for Up to 6 Guests With

Chicago, IL, United States

₹ 16,572
View Deal
Modern 2BR 420 Friendly in Chicago South Loop Near Museum Campus, McCormick Place and Soldier Field Photo
No. 4 most popular

Modern 2BR 420 Friendly in Chicago South Loop Near Museum Campus, McCormick Place and Soldier Field

Chicago, IL, United States

6.7
₹ 20,539
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Hostels and cheap hotels in Chicago

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

Homestay - Resting Good in Englewood

Chicago, IL, United States

₹ 3,611
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Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

₹ 4,444
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Homestay - The Lake House

Chicago, IL, United States

₹ 4,259
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Homestay - Close to lake and transportation

Chicago, IL, United States

₹ 4,536
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Homestay - Charming home in quite neighborhood

Chicago, IL, United States

₹ 4,259
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Homestay - Family close to transportation

Chicago, IL, United States

₹ 4,536
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Get the best value holiday rental in Chicago

These Chicago holiday rentals have the best prices for their ratings
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
₹ 6,944
View Deal
Wrigleyville Suites Photo

Wrigleyville Suites

3727 N Clifton Ave, Chicago, IL, United States

7.8
₹ 12,054
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Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

8.7
₹ 17,030
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Pulaski Point Properties Photo

Pulaski Point Properties

Chicago, IL, United States

9.7
₹ 12,101
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Chic, Cozy home, by Blue Line Train Stop + Free parking Photo

Chic, Cozy home, by Blue Line Train Stop + Free parking

Chicago, IL, United States

8.9
₹ 10,693
View Deal
Clean & Equipped 1br Apt Photo

Clean & Equipped 1br Apt

Chicago, IL, United States

9.1
₹ 11,105
View Deal

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago

Lux Apts with Lake Views and Top Amenities

Chicago, IL, United States

9.9
₹ 47,223

Entire Modern 2 Bedroom Apartment

Chicago, IL, United States

6.0
₹ 18,195

Homestay - Cozy Garden Apartment

Chicago, IL, United States

₹ 6,944

Homestay - Family close to transportation

Chicago, IL, United States

₹ 4,536

Homestay - Friendly Family in Chicago

Chicago, IL, United States

₹ 5,184
Hyde Park Modern Private Room - Near Univ of Chicago Photo

Hyde Park Modern Private Room - Near Univ of Chicago

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

7.4
₹ 12,035
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
₹ 6,944

Homestay - The Lake House

Chicago, IL, United States

₹ 4,259
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

9.4
₹ 54,870
1 Bedroom with Rooftop and Wrigley Views Photo

1 Bedroom with Rooftop and Wrigley Views

Chicago, IL, United States

8.8
₹ 20,368

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
₹ 19,534
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.9
₹ 15,701
Nice 2bedroom apartment steps away from UofChicago Photo

Nice 2bedroom apartment steps away from UofChicago

Chicago, IL, United States

₹ 10,924

Indulging 2BR Apartment in Festive Boystown - Buckingham 1

Chicago, IL, United States

9.4
₹ 17,350
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

8.7
₹ 17,030
Wrigley Field Mvp Suite 1 Bedroom Apartment Photo

Wrigley Field Mvp Suite 1 Bedroom Apartment

Chicago, IL, United States

9.3
₹ 33,621

La Villita - Gateway to Chicago

Chicago, IL, United States

7.8
₹ 20,275

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

₹ 4,259

A Hidden Gem, approx 15 mins to downtown Chicago!

Chicago, IL, United States

9.0
₹ 9,628

Convenient Cozy 2BR Loft with Optional Parking for 8 guests Near McCormick Place, Soldier Field and Lakefront Trail

Chicago, IL, United States

7.9
₹ 17,126

Useful insights on Chicago holiday rentals

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

Average Length of Stay

2 days
On average, people stay for 2 days when lodging at holiday rentals in Chicago. The average accommodation price for 2 days in Chicago in the past week is ₹ 56,947.

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 seasonAprilcheapest month to stay
High seasonOctobermost expensive time to stay
37%expected price decrease
44%expected price increase

Price

₹ 13,219 - ₹ 37,555

Cheapest day of weekSundayis the cheapest day of the week to book
Highest day of weekMondayis the most expensive day of the week to book
₹ 17,704
₹ 31,684

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?

2 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 ₹ 29,641 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 April. The cost of your apartment or rental property can be around 37% cheaper in April 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 Grand Boulevard, Lake View, and Lincoln Park.

How many operators does momondo search for hotels in Chicago?

As of April 2026, there are 2,636 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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