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Hotels in Chicago

Vacation rentals in Chicago, IL

Find deals on 3,688 vacation rentals in Chicago, IL

Chicago, IL, United States
21 Jul — 22 Jul2

momondo compares 3M+ hotel and accommodation options.

Top rentals in Chicago

Find the perfect vacation rental for your stay in Chicago
Price
C$ 53
C$ 613
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

C$ 465
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4 #1S - 4 Bedroom / 1.5 Bath Condo near McCormick Place, Wintrust Arena Photo
#1 Most popular

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

Chicago, IL, United States

C$ 663
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O'Hare
Search rentals in O'Hare
Luxurious New Remodeled Photo
Best value

Luxurious New Remodeled

Chicago, IL, United States

10.0
C$ 166
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Personal Gym Luxury Balcony Condo Photo
#1 Most popular

Personal Gym Luxury Balcony Condo

Chicago, IL, United States

10.0
C$ 209
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#2 Most popular

Luxurious Condo in Top Rated Neighborhood

Chicago, IL, United States

1.0
C$ 190
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#3 Most popular

Luxury King Bed in Family Friendly Location

Chicago, IL, United States

10.0
C$ 187
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Rogers Park
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Chicago Getaway Photo
Best value

Chicago Getaway

Chicago, IL, United States

2.0
C$ 78
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Urban Chicago Escape about 1 Mi to Local Beaches! Photo
#1 Most popular

Urban Chicago Escape about 1 Mi to Local Beaches!

Chicago, IL, United States

9.0
C$ 284
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Apartment by the lake Photo
#2 Most popular

Apartment by the lake

Chicago, IL, United States

8.8
C$ 367
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#3 Most popular

Walking distance to Lake Michigan, shops and restaurants.

Chicago, IL, United States

C$ 193
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#4 Most popular

Lovely 2br Rogers Park Home With Equippe

Chicago, IL, United States

C$ 248
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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

C$ 162
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Chicago Condo Near Lincoln Park and DePaul! Photo
#1 Most popular

Chicago Condo Near Lincoln Park and DePaul!

Chicago, IL, United States

9.5
C$ 424
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Entire Building-Walk To Lincoln Park Or The Beach Photo
#2 Most popular

Entire Building-Walk To Lincoln Park Or The Beach

Chicago, IL, United States

10.0
C$ 1,263
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Lincoln Park Living - Suite 2 Photo
#3 Most popular

Lincoln Park Living - Suite 2

Chicago, IL, United States

9.3
C$ 359
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#4 Most popular

Cozy Condo Sleeps 4

Chicago, IL, United States

7.0
C$ 296
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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
C$ 181
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Sonder by Marriott Bonvoy The Opal Apartments River North Photo
#1 Most popular

Sonder by Marriott Bonvoy The Opal Apartments River North

Chicago, IL, United States

8.7
C$ 303
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Chic River North Retreat Photo
#2 Most popular

Chic River North Retreat

Chicago, IL, United States

8.6
C$ 484
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Aurelien Spacious Apartments in the Heart of Gold Coast Photo
#3 Most popular

Aurelien Spacious Apartments in the Heart of Gold Coast

Chicago, IL, United States

8.5
C$ 767
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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
C$ 49
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5430 Happy Home

Chicago, IL, United States

8.1
C$ 61
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Homestay - Cozy & Pretty Monthly Females

Chicago, IL, United States

C$ 49
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Homestay - The Lake House

Chicago, IL, United States

C$ 63
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Close to Downtown - Free Parking

Chicago, IL, United States

10.0
C$ 53
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Homestay - Classic Chicago Bungalow

Chicago, IL, United States

C$ 63
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Get the best value vacation rental in Chicago

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

Kayak Starved Rock Campground

Ottawa, IL, United States

9.3
C$ 49
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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

8.0
C$ 198
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Fully furnished bedroom near medical district and UIC Photo

Fully furnished bedroom near medical district and UIC

Chicago, IL, United States

8.7
C$ 86
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Pulaski Point Properties Photo

Pulaski Point Properties

Chicago, IL, United States

9.8
C$ 217
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Luxurious New Remodeled Photo

Luxurious New Remodeled

Chicago, IL, United States

10.0
C$ 166
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The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.6
C$ 190
View Deal

momondo's favourite vacation rentals in Chicago

Learn more about these user-preferred vacation rentals in Chicago
Roscoe Village Guesthouse Photo

Roscoe Village Guesthouse

Chicago, IL, United States

8.0
C$ 312

STUDIO in vivid South Loop close to the Grant Park

Chicago, IL, United States

7.6
C$ 215
The Avondale Attic Photo

The Avondale Attic

Chicago, IL, United States

9.6
C$ 190

Wrigleyville Suites

Chicago, IL, United States

6.6
C$ 246
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
C$ 633

Homestay - The Lake House

Chicago, IL, United States

C$ 63
Chic Chicago Retreat home Photo

Chic Chicago Retreat home

Chicago, IL, United States

8.0
C$ 277
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
C$ 216
Apartment in Historic Lakeview Mansion - Best Location for Vacationers! Photo

Apartment in Historic Lakeview Mansion - Best Location for Vacationers!

Chicago, IL, United States

C$ 185

Cozy Studio near Wrigley field and Boystown

Chicago, IL, United States

8.6
C$ 170

Afrique Francaise de Woodlawn 1

Chicago, IL, United States

9.3
C$ 114

Hyde Park Modern Private Room - Near Univ of Chicago

Chicago, IL, United States

8.7
C$ 137

Chicago Condo with Balcony Walk to CTA Stations!

Chicago, IL, United States

9.6
C$ 375
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
C$ 485

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

Chicago, IL, United States

8.3
C$ 385
Sonder Jewelers Row | One-Bedroom Apartment Photo

Sonder Jewelers Row | One-Bedroom Apartment

Chicago, IL, United States

C$ 219

Cozy 2 Br 1 Ba Flat Just 10 Mins From Downtown

Chicago, IL, United States

6.0
C$ 238
Wrigleyville Inn Allstar Unit Photo

Wrigleyville Inn Allstar Unit

Chicago, IL, United States

9.7
C$ 902

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

Chicago, IL, United States

8.7
C$ 183

15 min Ohare/Rivers Casino/Downtown & Parking2

Chicago, IL, United States

6.6
C$ 186

Useful insights on Chicago vacation rentals

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

Lowest Vacation Rental Price

C$ 53
The cheapest price for a room in Chicago found in the last 7 days is C$ 53/night. This rate is available with Close to Downtown - Free Parking.

When to book a vacation rental in Chicago

Check out the information below to find the best deal on a vacation rental in Chicago
Low seasonFebruarycheapest month to stay
High seasonNovembermost expensive time to stay
71%expected price decrease
72%expected price increase

Price

C$ 202 - C$ 2,551

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
C$ 303
C$ 614

Best neighbourhoods to book a vacation rental in Chicago

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

Price

C$ 532 - C$ 633

CHEAPEST NEIGHBOURHOOD IN CHICAGOLoop6% cheaperVacation rentals in Loop are the cheapest in Chicago at just C$ 532 per night on average
MOST EXPENSIVE NEIGHBOURHOOD IN CHICAGONear North Side11% more expensiveNear North Side has the highest priced vacation rentals in Chicago with properties averaging C$ 633 per night
MOST POPULAR NEIGHBOURHOOD IN CHICAGONear North Side39% more users visitedMore momondo users search for vacation 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 vacation apartments for in Chicago?

On average, people book vacation rentals in Chicago for stays of around 2 nights.

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

Vacation apartments in Chicago are often cheapest in February - rental prices can be around 72% lower than the average during this period.

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

Downtown is the most popular area of Chicago to book a rental apartment in. Near West Side and Near North Side are also sought-after places to stay.

How many operators does momondo search for hotels in Chicago?

There are 4,128 operators available for hotels in Chicago as of July 2025.

When did momondo last update prices for hotels in Chicago?

Prices for hotels in Chicago were last updated today.

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