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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
£35
£539
Review Score
0+
6+
7+
8+
9+

Holiday rentals in popular neighbourhoods in Chicago

Below are the most popular neighbourhoods in Chicago to stay in, as well as some of the best holiday rentals in each area
Lincoln Park
Search rentals in Lincoln Park
Best value

Walker's Paradise 1br Apartment In Lincoln Park - Lincoln 2501

Chicago, IL, United States

6.0
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
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
No. 3 most popular

Lincoln Park 3 Br Penthouse

Chicago, IL, United States

9.1
Hyde Park
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Best value

Hyde Park Shared Apartments

Chicago, IL, United States

7.7
No. 1 most popular

Lively & Fully Furnished 1br Apartment - Kenwood 408

Chicago, IL, United States

9.0
No. 2 most popular

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

Chicago, IL, United States

8.6
Bright & Cozy 1br Near Uchicago Photo
No. 3 most popular

Bright & Cozy 1br Near Uchicago

Chicago, IL, United States

9.0
Near South Side
Search rentals in Near South Side
Best value

Mccormick 2b 2ba for Up to 6 Guests With

Chicago, IL, United States

No. 1 most popular

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

Chicago, IL, United States

8.7
Mccormick Place Modern And Cosy 420 Frie Photo
No. 2 most popular

Mccormick Place Modern And Cosy 420 Frie

Chicago, IL, United States

7.0
Mccormick Place Skyline View 2br-2ba Wit Photo
No. 3 most popular

Mccormick Place Skyline View 2br-2ba Wit

Chicago, IL, United States

7.0
O'Hare
Search rentals in O'Hare
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
No. 1 most popular

Luxurious New Remodeled

Chicago, IL, United States

8.8
No. 2 most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0

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

Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

Homestay - The Lake House

Chicago, IL, United States

Homestay - Close to lake and transportation

Chicago, IL, United States

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

Homestay - Family close to transportation

Chicago, IL, United States

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

8.7
Condo Apartment Near Midway Airport Photo

Condo Apartment Near Midway Airport

Chicago, IL, United States

9.1
Level Chicago - River North Photo

Level Chicago - River North

369 West Grand Avenue, Chicago, IL, United States

8.8
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.9
Peaceful place Great location food markets transportation downtown lake Michigan Photo

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago, IL, United States

8.6
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago

Close to Downtown - Free Parking

Chicago, IL, United States

7.5
£50

Hyde Park Shared Apartments

Chicago, IL, United States

7.7
£90

Homestay - Close to lake and transportation

Chicago, IL, United States

£36

Homestay - Friendly Family in Chicago

Chicago, IL, United States

£42

Indoor Pool Gym Rooftop-215-by Cloud9

215 West Lake Street, Chicago, IL, United States

8.3
£323

Homestay - Resting Good in Englewood

Chicago, IL, United States

£29

Afrique Francaise de Woodlawn 2

Chicago, IL, United States

7.4
£74
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

9.2
£688
Artistic Loft Rooftop Uptown Montrose Beach Gymwfh Photo

Artistic Loft Rooftop Uptown Montrose Beach Gymwfh

Chicago, IL, United States

9.9
£134
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
£97
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.5
£126

Wonderful Room Close to Downtown Chicago

Chicago, IL, United States

6.8
£146
Mccormick Place Modern And Cosy 420 Frie Photo

Mccormick Place Modern And Cosy 420 Frie

Chicago, IL, United States

7.0
£198

Indulging 2BR Apartment in Festive Boystown - Buckingham 1

Chicago, IL, United States

9.5
£152
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

8.7
£204

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
£157

Beautiful 4 bedroom 2 bathroom apartment near everything

Chicago, IL, United States

7.3
£263

1 Bedroom with Rooftop and Wrigley Views

Chicago, IL, United States

9.3
£219

Entire Modern 2 Bedroom Apartment

Chicago, IL, United States

7.3
£175

Splendid & Fully Furnished 1br Apartment - Broadway 204 Rep

Chicago, IL, United States

9.0
£162

Useful insights on Chicago holiday rentals

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

Average Length of Stay

5 days
On average, people stay for 5 days when lodging at holiday rentals in Chicago. The average accommodation price for 5 days in Chicago in the past week is £650.

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 weekSundayis the cheapest day of the week to book
Highest day of weekFridayis the most expensive day of the week to book
£187is the average per night cost for a holiday rental on this day
£274is 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 holiday rental in Chicago

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

On average, people book holiday rentals in Chicago for stays of around 5 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 £220 per night.

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

Holiday apartments in Chicago are often cheapest in January - rental prices can be around 48% lower than the average during this period.

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

Downtown, Near North Side, and Uptown are typically the most popular places to rent holiday apartments in Chicago.

How many operators does momondo search for hotels in Chicago?

The number of operators available for hotels in Chicago is 2,686 as of June 2026.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago are updated daily.

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