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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
€34
€593
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
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Lincoln Park Living - 3 Queen Beds - Sleeps 6 Photo
Best value

Lincoln Park Living - 3 Queen Beds - Sleeps 6

Chicago, IL, United States

9.1
€136
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No. 1 most popular

Entire Apartment In Heart Of Lincoln Park & Lake Sea And Beach

Chicago, IL, United States

7.7
€209
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No. 2 most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.2
€198
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No. 3 most popular

1BR Apt in Lincoln Park - Lincoln 3E

Chicago, IL, United States

5.0
€190
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Hyde Park
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Best value

Hyde Park Shared Apartments

Chicago, IL, United States

6.0
€106
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No. 1 most popular

Lively 1br - Kenwood 408

Chicago, IL, United States

€190
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No. 2 most popular

Cozy Studio in Hyde Park - BS 226 rep

Chicago, IL, United States

5.0
€196
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No. 3 most popular

1br Cozy Apt - Harper 404

Chicago, IL, United States

€279
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Near South Side
Search rentals in Near South Side
Best value

Mccormick 2b 2ba for Up to 6 Guests With

Chicago, IL, United States

€157
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No. 1 most popular

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

Chicago, IL, United States

8.7
€270
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No. 2 most popular

Mccormick Place Skyline View 2br-2ba Wit

Chicago, IL, United States

7.1
€236
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No. 3 most popular

Mccormick Place Modern And Cosy 420 Frie

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

6.9
€407
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No. 4 most popular

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

Chicago, IL, United States

9.3
€204
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North Center
Search rentals in North Center
Best value

The Lyons' Den

Chicago, IL, United States

9.8
€143
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No. 1 most popular

Lyons' Suite

Chicago, IL, United States

8.3
€307
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The Lyons' Lair Photo
No. 2 most popular

The Lyons' Lair

Chicago, IL, United States

9.5
€284
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No. 3 most popular

3BR Comfy & Bright Apt in North Center

Chicago, IL, United States

7.7
€444
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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

1070240045

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

1070239888

Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

1070240035

Homestay - Close to lake and transportation

Chicago, IL, United States

11179024

Homestay - The Lake House

Chicago, IL, United States

1070239309

Homestay - Family close to transportation

Chicago, IL, United States

1070240020

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
€195
View Deal
1071986668
Level Chicago - Fulton Market Photo

Level Chicago - Fulton Market

354 North Union Avenue, Chicago, IL, United States

7.3
€192
View Deal
9474213
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
€251
View Deal
7682996
Condo Apartment Near Midway Airport Photo

Condo Apartment Near Midway Airport

Chicago, IL, United States

9.0
€117
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1071795854
Lower level luxury Photo

Lower level luxury

Chicago, IL, United States

9.5
11226950
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
€147
View Deal
8002184

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago
Livn West Loop Chicago Classic Queen Studio Photo

Livn West Loop Chicago Classic Queen Studio

Chicago, IL, United States

9.0
€176
Iconic Downtown Penthouses Getaway + City Views Photo

Iconic Downtown Penthouses Getaway + City Views

Chicago, IL, United States

9.1
€1,209
Livn West Loop Chicago Queen Superior Studio Photo

Livn West Loop Chicago Queen Superior Studio

Chicago, IL, United States

9.3
€189
747 Lofts by RedAwning - River West, Second Floor Chicago Photo

747 Lofts by RedAwning - River West, Second Floor Chicago

Chicago, IL, United States

8.2
€177
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
€114

Beautiful 4 bedroom 2 bathroom apartment near everything

Chicago, IL, United States

6.4
€261
Livn Millennium Park Downtown Chicago 1 Br Photo

Livn Millennium Park Downtown Chicago 1 Br

Chicago, IL, United States

9.2
€184

Mccormick Place Skyline View 2br-2ba Wit

Chicago, IL, United States

7.1
€236
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.9
€190

Chic 2br Escape - Buckingham 1

Chicago, IL, United States

7.2
€275

Homestay - The Lake House

Chicago, IL, United States

€40

Mccormick Place Modern And Cosy 420 Frie

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

6.9
€407
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
€251
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
€147

La Villita - Gateway to Chicago

Chicago, IL, United States

6.6
€200
Livn Millennium Park Downtown Chicago Studio Photo

Livn Millennium Park Downtown Chicago Studio

Chicago, IL, United States

8.6
€195

Beautiful Big 3 bedroom Quiet Apt near downtown

Chicago, IL, United States

8.4
€262

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
€185

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

€40
Cozy apartment with AC and WiFi in awesome Chicago Photo

Cozy apartment with AC and WiFi in awesome Chicago

Chicago, IL, United States

7.6
€252

Useful insights on Chicago holiday 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 holiday rentals in Chicago. The average accommodation price for 3 days in Chicago in the past week is €234.

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 weekFridayis the cheapest day of the week to book
Highest day of weekSaturdayis the most expensive day of the week to book
€189is the average per night cost for a holiday rental on this day
€399is the average per night cost for a holiday rental on this day

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?

Those choosing holiday rental apartments in Chicago typically book for at least 3 nights.

How much does a holiday rental apartment in Chicago cost?

Renting a holiday apartment in Chicago will see a range in pricing typically determined by the season, location of the apartment and the number of rooms required. Recently, a typical search for apartment rentals in Chicago suggests an average of €301 per night.

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

January is typically when Chicago holiday apartment and rental property prices are at their lowest, with prices around 47% lower than the Chicago peak 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, Near West Side, and Near North Side.

How many operators does momondo search for hotels in Chicago?

There are 2,560 operators available for hotels in Chicago as of July 2026.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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