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Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on 3,490 holiday rentals in Chicago, IL

Chicago, IL, United States
23 Sep — 24 Sep2

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Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
Price
€45
€343
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
Downtown
Search rentals in Downtown
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown Photo
Best value

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago, IL, United States

10.0
€290
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O'Hare
Search rentals in O'Hare
Luxurious New Remodeled Photo
Best value

Luxurious New Remodeled

Chicago, IL, United States

9.0
Personal Gym Luxury Balcony Condo Photo
No. 1 most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
€101
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No. 2 most popular

Luxurious Condo in Top Rated Neighborhood

Chicago, IL, United States

1.0
€140
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No. 3 most popular

Luxury King Bed in Family Friendly Location

Chicago, IL, United States

10.0
€117
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Rogers Park
Search rentals in Rogers Park
Best value

Homestay - Clean Modern Loyola/Northwestern

Chicago, IL, United States

Urban Chicago Vacation Rental Condo Near Beach! Photo
No. 1 most popular

Urban Chicago Vacation Rental Condo Near Beach!

Chicago, IL, United States

9.1
€155
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Sunlit Studio with City Charm Photo
No. 2 most popular

Sunlit Studio with City Charm

Chicago, IL, United States

5.0
€118
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Urban Chicago Escape ~ 1 Mi to Local Beaches! Photo
No. 3 most popular

Urban Chicago Escape ~ 1 Mi to Local Beaches!

Chicago, IL, United States

9.1
€180
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Elegant and Chic 2Bed 2Bath steps from the lake! Photo
No. 4 most popular

Elegant and Chic 2Bed 2Bath steps from the lake!

Chicago, IL, United States

10.0
€237
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Near North Side
Search rentals in Near North Side
Best value

Chicago Downtown River North

Chicago, IL, United States

6.0
€112
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Sonder by Marriott Bonvoy Onterie Apartments Magnificent Mile Photo
No. 1 most popular

Sonder by Marriott Bonvoy Onterie Apartments Magnificent Mile

Chicago, IL, United States

8.2
€126
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Sonder by Marriott Bonvoy The Opal Apartments River North Photo
No. 2 most popular

Sonder by Marriott Bonvoy The Opal Apartments River North

Chicago, IL, United States

8.7
€137
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Kasa River North Chicago Photo
No. 3 most popular

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
€167
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Lincoln Park
Search rentals in Lincoln Park
Historic Old Town One Bedroom Suite Photo
Best value

Historic Old Town One Bedroom Suite

Chicago, IL, United States

Chicago Condo Near Lincoln Park and DePaul! Photo
No. 1 most popular

Chicago Condo Near Lincoln Park and DePaul!

Chicago, IL, United States

9.5
€245
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Lincoln Park Living - Suite 2 Photo
No. 2 most popular

Lincoln Park Living - Suite 2

1147 West Diversey Parkway, Chicago, IL, United States

9.1
€167
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Walk to Lincoln Park, North Avenue Beach, and Second City! Lovely Old Town Charm! by AllSet Turnover Photo
No. 3 most popular

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

Chicago, IL, United States

9.4
€175
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Entire Building-Walk To Lincoln Park Or Photo
No. 4 most popular

Entire Building-Walk To Lincoln Park Or

1147 West Diversey Parkway, Chicago, IL, United States

9.4
€540
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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 - Cozy & Pretty Monthly Females

Chicago, IL, United States

Homestay - Charming home in quite neighborhood

Chicago, IL, United States

Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

Homestay - Family close to transportation

Chicago, IL, United States

Homestay - The Lake House

Chicago, IL, United States

Homestay - Convenient Room w/Private Bathroom

Chicago, IL, United States

Get the best value holiday rental in Chicago

These Chicago holiday rentals have the best prices for their ratings
Cozy 1 Bedroom Close To Downtown Chicago Photo

Cozy 1 Bedroom Close To Downtown Chicago

1335 North Greenview Avenue Apt 1F, Chicago, IL, United States

8.7
€226
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Luxurious New Remodeled Photo

Luxurious New Remodeled

Chicago, IL, United States

9.0
Kasa River North Chicago Photo

Kasa River North Chicago

808 North Wells Street, Chicago, IL, United States

9.1
€167
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River West, Third Floor Chicago by 747 Lofts Photo

River West, Third Floor Chicago by 747 Lofts

747 N May St., Chicago, IL, United States

8.1
€110
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Dorothy's Photo

Dorothy's

3445 North Halsted Street, Chicago, IL, United States

7.6
Personal Gym Luxury Balcony Condo Photo

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
€101
View Deal

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago
The Neighborhood Hotel Little Italy Photo

The Neighborhood Hotel Little Italy

Chicago, IL, United States

9.1
€237
Cozy Garden studio Apartment Photo

Cozy Garden studio Apartment

Chicago, IL, United States

€64
Nice 2bedroom apartment steps away from UofChicago Photo

Nice 2bedroom apartment steps away from UofChicago

Chicago, IL, United States

€92
The Double Play- Wrigley Flats Located Right next to Wrigley - Cubs! Photo

The Double Play- Wrigley Flats Located Right next to Wrigley - Cubs!

Chicago, IL, United States

7.8
€192

Chicago Downtown River North

Chicago, IL, United States

6.0
€112
Pulaski Point Properties Photo

Pulaski Point Properties

Chicago, IL, United States

9.7
€136

Homestay - Family close to transportation

Chicago, IL, United States

€41

Penthouse Level, Stunning Wrigley Stay

820 West Newport Avenue Unit 3, Chicago, IL, United States

8.6
€406
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.4
€163
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

8.4
€302

Homestay - The Lake House

Chicago, IL, United States

€39

Beautiful Home Near Downtwon - Free Parking!

Chicago, IL, United States

10.0
€48

Homestay - Here's a clean and peaceful room.

Chicago, IL, United States

€37
Roscoe Village Guesthouse Photo

Roscoe Village Guesthouse

Chicago, IL, United States

8.0
€194

Homestay - Friendly Family in Chicago

Chicago, IL, United States

€47
Chic Chicago Retreat home Photo

Chic Chicago Retreat home

Chicago, IL, United States

8.0
€162
Level Chicago - Fulton Market Photo

Level Chicago - Fulton Market

354 North Union Avenue, Chicago, IL, United States

7.4
€208

Hyde Park Modern Private Room - Near Univ of Chicago

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

7.4
€89

A Hidden Gem, approx 15 mins to downtown Chicago!

Chicago, IL, United States

7.9
€83

Super Amazing Place To Stay Near Downtown! Free Parking

Chicago, IL, United States

10.0
€46

Useful insights on Chicago holiday rentals

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

Lowest Holiday Rental Price

€37
The cheapest price for a room in Chicago found in the last 7 days is €37/night. This rate is available with Homestay - Here's a clean and peaceful room..

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 seasonDecembercheapest month to stay
High seasonMarchmost expensive time to stay
30%expected price decrease
50%expected price increase

Price

€155 - €441

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
€180
€302

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

€229 - €291

CHEAPEST NEIGHBOURHOOD IN CHICAGONear North Side15% cheaperHoliday rentals in Near North Side are the cheapest in Chicago at just €229 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGOLoop7% more expensiveLoop has the highest priced holiday rentals in Chicago with properties averaging €291 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side47% more users visitedMore momondo users search for holiday rentals in Near North Side 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?

Those choosing holiday rental apartments in Chicago typically book for at least 5 nights.

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

December is typically when Chicago holiday apartment and rental property prices are at their lowest, with prices around 30% 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 Grand Boulevard, Lincoln Park, and Logan Square.

How many operators does momondo search for hotels in Chicago?

There are 4,019 operators available for hotels in Chicago as of September 2025.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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