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Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on holiday rentals in Chicago, IL

momondo compares 3M+ hotel and accommodation options.

Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
Price
₹ 4,688
₹ 59,987
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

9.3
₹ 10,335
View Deal
No. 1 most popular

Entire Apartment in Heart of Lincoln Par

Chicago, IL, United States

4.8
₹ 51,483
View Deal
Charming & Bright Multilevel Townhome with Parking Photo
No. 2 most popular

Charming & Bright Multilevel Townhome with Parking

Chicago, IL, United States

8.0
₹ 35,039
View Deal
No. 3 most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.1
₹ 24,019
View Deal
Hyde Park
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Best value

Hyde Park Shared Apartments

Chicago, IL, United States

4.8
₹ 11,579
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Cozy Studio in Hyde Park-Walk to Lake & University Photo
No. 1 most popular

Cozy Studio in Hyde Park-Walk to Lake & University

Chicago, IL, United States

8.2
₹ 13,179
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No. 2 most popular

Lively 1br - Kenwood 408

Chicago, IL, United States

₹ 20,765
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No. 3 most popular

Cozy Studio in Hyde Park - BS 226 rep

Chicago, IL, United States

5.0
₹ 21,340
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Near South Side
Search rentals in Near South Side
Best value

Perfect for Couple Studio South Loop Stay Near McCormick, Aquarium & Lake Michigan

Chicago, IL, United States

7.3
₹ 14,496
View Deal
No. 1 most popular

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

Chicago, IL, United States

8.8
₹ 38,469
View Deal
South Loop Chicago 2BR Retreat with Skyline View and Optional Parking for 8 guests Near McCormick Place and Soldier Field Photo
No. 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
₹ 19,358
View Deal
Mccormick Place Modern And Cosy 420 Frie Photo
No. 3 most popular

Mccormick Place Modern And Cosy 420 Frie

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

6.9
₹ 44,402
View Deal
South Loop 2br Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College Photo
No. 4 most popular

South Loop 2br Retreat Near Grant Park, Soldier Field, Adler Planetarium & Columbia College

Chicago, IL, United States

9.4
₹ 16,588
View Deal
North Center
Search rentals in North Center
Best value

The Lyons' Den

Chicago, IL, United States

9.6
₹ 14,449
View Deal
No. 1 most popular

Lyons' Suite

Chicago, IL, United States

9.5
₹ 45,677
View Deal
The Lyons' Lair Photo
No. 2 most popular

The Lyons' Lair

Chicago, IL, United States

9.6
₹ 18,947
View Deal
No. 3 most popular

3BR Comfy & Bright Apt in North Center

Chicago, IL, United States

7.7
₹ 48,421
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

₹ 3,158
View Deal
1071913881

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

₹ 4,402
View Deal
1070239888

Homestay - Chicago, Home of Presidents!

Chicago, IL, United States

₹ 3,349
View Deal
10379428

Homestay - Friendly Homestay

Chicago, IL, United States

₹ 4,402
View Deal
10379883

Homestay - The Lake House

Chicago, IL, United States

₹ 4,402
View Deal
1070239309

Homestay - Close to lake and transportation

Chicago, IL, United States

₹ 4,689
View Deal
11179024

Get the best value holiday rental in Chicago

These Chicago holiday 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
₹ 15,876
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
₹ 9,783
View Deal
11343816
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.2
₹ 17,430
View Deal
7682996
Kasa Lake Shore Chicago Photo

Kasa Lake Shore Chicago

446 East Ontario Street, Chicago, IL, United States

7.9
₹ 15,780
View Deal
10781990
Sonder The Burnham Photo

Sonder The Burnham

555 West Jackson Boulevard, Chicago, IL, United States

7.9
₹ 12,344
View Deal
10190685
Relaxing Chicago Studio Photo

Relaxing Chicago Studio

Chicago, IL, United States

9.8
₹ 12,209
View Deal
11261579

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago

Homestay - Chicago, Home of Presidents!

Chicago, IL, United States

₹ 3,349
Livn Millennium Park Downtown Chicago Studio Photo

Livn Millennium Park Downtown Chicago Studio

Chicago, IL, United States

8.6
₹ 24,330

Homestay - Fun family that loves the outdoors.

Chicago, IL, United States

₹ 6,986

Indoor Pool Gym Rooftop-215-by Cloud9

215 West Lake Street, Chicago, IL, United States

8.3
₹ 41,531
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

8.0
₹ 14,758
Relaxing Chicago Studio Photo

Relaxing Chicago Studio

Chicago, IL, United States

9.8
₹ 12,209
Iconic Downtown Penthouses Getaway + City Views Photo

Iconic Downtown Penthouses Getaway + City Views

Chicago, IL, United States

9.0
₹ 295,787

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

Chicago, IL, United States

8.8
₹ 38,469

Homestay - The Lake House

Chicago, IL, United States

₹ 4,402
Livn West Loop Chicago 2 Br City View Photo

Livn West Loop Chicago 2 Br City View

Chicago, IL, United States

9.1
₹ 28,234

Afrique Francaise de Woodlawn 1

Chicago, IL, United States

8.1
₹ 9,037

Entire Modern 2 Bedroom Apartment

Chicago, IL, United States

7.8
₹ 18,340

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

₹ 4,402
Cozy Spacious Garden Unit Photo

Cozy Spacious Garden Unit

Chicago, IL, United States

₹ 13,772
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

₹ 9,761
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
₹ 19,358
Fulbrix Bright Designer Apartments with West Loop Views Photo

Fulbrix Bright Designer Apartments with West Loop Views

Chicago, IL, United States

9.2
₹ 55,443

Chic 2br Escape - Buckingham 1

Chicago, IL, United States

7.2
₹ 29,952
Regal Stylish Uptown Loft Beachfront Rooftopwfhgym Photo

Regal Stylish Uptown Loft Beachfront Rooftopwfhgym

Chicago, IL, United States

9.3
₹ 10,909
Mccormick Place Modern And Cosy 420 Frie Photo

Mccormick Place Modern And Cosy 420 Frie

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

6.9
₹ 44,402

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 ₹ 26,150.

When to book a holiday rental in Chicago

Check out the information below to find the best deal on a holiday rental in Chicago
Cheapest day of weekMondayis the cheapest day of the week to book
Highest day of weekSaturdayis the most expensive day of the week to book
₹ 16,645is the average per night cost for a holiday rental on this day
₹ 33,894is the average per night cost for a holiday rental on this day

Best neighbourhoods to book a holiday rental in Chicago

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

Price

₹ 24,577 - ₹ 29,720

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side12% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just ₹ 24,577 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGOLoop6% more expensiveLoop has the highest priced holiday rentals in Chicago with properties averaging ₹ 29,720 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGOLoop30% more users visitedMore momondo users search for holiday 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 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 ₹ 29,522 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 Grand Boulevard, Lake View, and Edgewater.

How many operators does momondo search for hotels in Chicago?

As of October 2026, there are 2,635 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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