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Hotels in Chicago

Holiday rentals in Chicago, IL

Find deals on 3,689 holiday rentals in Chicago, IL

Chicago, IL, United States
22 Jul — 23 Jul2

momondo compares 3M+ hotel and accommodation options.

Top rentals in Chicago

Find the perfect holiday rental for your stay in Chicago
Price
$59
$684
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

4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena Photo
No. 1 most popular

4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena

Chicago, IL, United States

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

Luxurious New Remodeled

Chicago, IL, United States

10.0
Personal Gym Luxury Balcony Condo Photo
No. 1 most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
No. 2 most popular

Luxurious Condo in Top Rated Neighborhood

Chicago, IL, United States

1.0
No. 3 most popular

Luxury King Bed in Family Friendly Location

Chicago, IL, United States

10.0
Rogers Park
Search rentals in Rogers Park
Chicago Getaway Photo
Best value

Chicago Getaway

Chicago, IL, United States

2.0
Urban Chicago Escape about 1 Mi to Local Beaches! Photo
No. 1 most popular

Urban Chicago Escape about 1 Mi to Local Beaches!

Chicago, IL, United States

9.0
Apartment by the lake Photo
No. 2 most popular

Apartment by the lake

Chicago, IL, United States

8.8
No. 3 most popular

Walking distance to Lake Michigan, shops and restaurants.

Chicago, IL, United States

No. 4 most popular

Lovely 2br Rogers Park Home With Equippe

Chicago, IL, United States

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
Entire Building-Walk To Lincoln Park Or The Beach Photo
No. 2 most popular

Entire Building-Walk To Lincoln Park Or The Beach

Chicago, IL, United States

10.0
$1,406
View Deal
Lincoln Park Living - Suite 2 Photo
No. 3 most popular

Lincoln Park Living - Suite 2

Chicago, IL, United States

9.3
No. 4 most popular

Cozy Condo Sleeps 4

Chicago, IL, United States

7.0
Near North Side
Search rentals in Near North Side
Best value

Chicago Downtown River North

Chicago, IL, United States

6.0
Sonder by Marriott Bonvoy The Opal Apartments River North Photo
No. 1 most popular

Sonder by Marriott Bonvoy The Opal Apartments River North

Chicago, IL, United States

8.7
Chic River North Retreat Photo
No. 2 most popular

Chic River North Retreat

Chicago, IL, United States

8.6
Aurelien Spacious Apartments in the Heart of Gold Coast Photo
No. 3 most popular

Aurelien Spacious Apartments in the Heart of Gold Coast

Chicago, IL, United States

8.5

Hostels and cheap hotels in Chicago

These hotels and hostels usually make for a cheap way to stay in Chicago
Kayak Starved Rock Campground Photo

Kayak Starved Rock Campground

Ottawa, IL, United States

9.3

5430 Happy Home

Chicago, IL, United States

8.1

Homestay - Cozy & Pretty Monthly Females

Chicago, IL, United States

Homestay - The Lake House

Chicago, IL, United States

Close to Downtown - Free Parking

Chicago, IL, United States

10.0

Homestay - Classic Chicago Bungalow

Chicago, IL, United States

Get the best value holiday rental in Chicago

These Chicago holiday rentals have the best prices for their ratings
Kayak Starved Rock Campground Photo

Kayak Starved Rock Campground

Ottawa, IL, United States

9.3
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

8.0
Fully furnished bedroom near medical district and UIC Photo

Fully furnished bedroom near medical district and UIC

Chicago, IL, United States

8.7
Pulaski Point Properties Photo

Pulaski Point Properties

Chicago, IL, United States

9.8
Luxurious New Remodeled Photo

Luxurious New Remodeled

Chicago, IL, United States

10.0
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.6

momondo's favourite holiday rentals in Chicago

Learn more about these user-preferred holiday rentals in Chicago
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.6
$213

Wrigleyville Suites

Chicago, IL, United States

6.6
$273
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
$704

Homestay - The Lake House

Chicago, IL, United States

$70
Chic Chicago Retreat home Photo

Chic Chicago Retreat home

Chicago, IL, United States

8.0
$308
Lovely 2 Bed 3 Miles from DT w Free Parking Photo

Lovely 2 Bed 3 Miles from DT w Free Parking

Chicago, IL, United States

7.7
$249
Apartment in Historic Lakeview Mansion - Best Location for Vacationers! Photo

Apartment in Historic Lakeview Mansion - Best Location for Vacationers!

Chicago, IL, United States

$206

Cozy Studio near Wrigley field and Boystown

Chicago, IL, United States

8.6
$189

Afrique Francaise de Woodlawn 1

Chicago, IL, United States

9.3
$127

Hyde Park Modern Private Room - Near Univ of Chicago

Chicago, IL, United States

8.7
$153

Chicago Condo with Balcony Walk to CTA Stations!

Chicago, IL, United States

9.6
$419
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square Photo

Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

Chicago, IL, United States

9.0
$543

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

Chicago, IL, United States

8.3
$429
Sonder Jewelers Row | One-Bedroom Apartment Photo

Sonder Jewelers Row | One-Bedroom Apartment

Chicago, IL, United States

$245

Cozy 2 Br 1 Ba Flat Just 10 Mins From Downtown

Chicago, IL, United States

6.0
$266
Wrigleyville Inn Allstar Unit Photo

Wrigleyville Inn Allstar Unit

Chicago, IL, United States

9.7
$1,008

Modern 1BR Apartment Laundry Included- Brompton 55-57 rep

Chicago, IL, United States

8.7
$205

15 min Ohare/Rivers Casino/Downtown & Parking2

Chicago, IL, United States

6.6
$208
Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking Photo

Cozy 1 bedroom, 1 min from Irving Park Blue line, free parking

Chicago, IL, United States

9.0
$257
The Roscoe Village Guesthouse Photo

The Roscoe Village Guesthouse

Chicago, IL, United States

9.9
$349

Useful insights on Chicago holiday rentals

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

Lowest Holiday Rental Price

$60
The cheapest price for a room in Chicago found in the last 7 days is $60/night. This rate is available with Close to Downtown - Free Parking.

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 seasonFebruarycheapest month to stay
High seasonNovembermost expensive time to stay
71%expected price decrease
72%expected price increase

Price

$226 - $2,850

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
$338
$686

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

$594 - $707

CHEAPEST NEIGHBOURHOOD IN CHICAGOLoop6% cheaperHoliday rentals in Loop are the cheapest in Chicago at just $594 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear North Side11% more expensiveNear North Side has the highest priced holiday rentals in Chicago with properties averaging $707 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side39% 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?

5 nights is the typical length of a Chicago holiday rental booking.

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

February is often the cheapest month to rent a holiday apartment in Chicago. Prices per night can be around 72% below average at this time.

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

Near North Side and West Town are classic choices for holiday rentals in Chicago. Recently, many users have found good rental properties in Edgewater too.

How many operators does momondo search for hotels in Chicago?

As of July 2025, there are 4,127 operators available to choose from for hotels in Chicago.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago are updated daily.

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Free cancellation

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