Chicago Vacation Rentals

Find the best deals on 1,372 vacation rentals in Chicago

Top rentals in Chicago

Find the perfect Chicago vacation rental for your needs

Pittsfield Apartments + Suites

6.6

$91

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May street Apartel

$72

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Loop Suites

6.8

$80

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Right Downtown near Millennium Park

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The Penthouse at Grand Plaza

9.4

$389

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Oakwood 200 Squared

10.0

$116

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Private Room #2, near O'Hare airport,

$44

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The place - Amazing apt - Ukrainian village

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Stay Alfred At The Seneca

$145

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Beautiful 2 bedroom in Bucktown , Chicago

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Room in Condo near Univ of Chicago

5.5

$57

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Beautiful Bronzeville Penthouse

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Your Perfect Accommodation At Dch 215 West Lake Street

7.5

$92

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Sonder Roosevelt Suites Lovely 1br + Laundry

$139

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Downtown Lincoln Park Abode With Private Entrance

$145

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Stay Alfred at The Ace on Ashland

$114

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River West 2 Bed / Near Downtown

$99

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River North Waterside Condos

$144

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Pilsen Roadhouse

8.0

$119

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Highly Rated Private One Bedroom Apartment: A+ Bucktown/Wicker Park Location

$114

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Amazing 3-Bedroom Garden Condo Near U Of C

9.4

$161

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Two-Bedroom On N Milwaukee Avenue Apt 3w (Chi - N - Milw1574)

$182

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Comfortable studio in Chicago

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Homan Square

5.2

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A Duplex for your Grouplex

$135

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A Short Walk From From Wrigley Field - 2 Brm

$294

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Millennium Park River King Bed

$139

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2 Bed 2 Bath Condo In River West

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Wrigleyville Private Guesthouse

10.0

$359

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Lasalle Lodge

5.7

$18

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Loop / Grant Park -2 and 3 Bedrooms / 2 bathrooms

$138

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Peaceful Accommodations

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Newly Renovated 1200 Sq/Ft Apartment. Sleeps 5

9.2

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Awesome Artsy 1 Bdr Loft Near Park & Train

7.3

$106

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The Mozart - Contemporary Logan Square 3bdr

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Furnished Suites in South Loop Chicago

$155

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Celeste Celebrity Suites

$163

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Cute place, convenient to everything in the city

8.4

$62

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Ginosi 747 Apartel

$75

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Apartment In River North With Balcony

$159

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Stay in hot Wicker Park Area!

$147

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Loft-Style 2BR in South Loop by Sonder

$221

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Bucktown, Urban Luxury And Convenience. 2 Minutes To L Train Stop At Western

9.2

$280

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4 bedroom 2 bath perfect for Mccormick place and museum visitors

$301

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A Beautiful Terraced Artist Duplex Loft Chic Space

$140

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Location Location Location 2br/2ba In the Heart of the City

$284

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New listing Spacious in Humboldt Heights Close to night life and bus

8.0

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Pet Friendly W Parking! 15 Min To Loop, Mccormick & Midway! Sleeps 6

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Suite w/ balcony, pool, fitness center, & skyline views at Grand Plaza! Dogs ok!

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Vibrant 2BR/2.5BA Apt near Museum Campus by Domio

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Walk To Everything Downtown Great 2bd/2ba Family Condo

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Stay Alfred at Park Michigan

$137

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Best Deal 2br Apt Near Restaurants, Starbucks

7.6

$152

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Beautiful Room in Chicago

7.1

$66

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Premier Luxury at the Coast

$100

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Corporate Suites Network - 845 N State

$136

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Sonder - Lincoln Park Zoo

9.2

$173

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Sonder - Six Points - Stunning 2br

9.9

$131

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Corporate Suites in the Heart of Magnificent Mile

$136

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Two-Bedroom on N Southport Avenue Apt 3

$144

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Sonder Roosevelt Suites Cozy 1br + Laundry

$158

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Convenience Is Key Just 2 Blocks To The Brown Line 'L'

$274

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Recently Gut Rehabbed Unit In One Of Chicago's Trendiest Neighborhoods!

9.0

$172

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Andersonvillevr

9.9

$279

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Roscoe Village Inn Guesthouse Walk To Chicago's Wrigley Field

10.0

$256

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Stunning Logan Square Area Bungalow! A Rare Single Family Home In Chicago

$330

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Sonder - The Western

9.0

$141

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Luxury Apartments at McCormick Place by Cloud9

$294

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Chic Horner Park Sandstone

8.0

$170

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6min To The Bean + Netflix

$137

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Quaint & Cozy Southside Guest Rm; Near Transit, U. Chicago, Historic Bronzeville

$165

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New 2-Level Home Near Wrigley

$149

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Scandinavian Designer Condo Near Train & Food

$102

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Elegant Designer Home Walk to Train & Restaurants! E2

$100

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Bright And Beautiful, 1 bdrm, 1alcove, 2 qwn beds, I bath, hip Logan square!

9.6

$136

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King Bed, Full Kitchen & Netflix

$216

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Modern 1br Apt In Loop By Domio

$174

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Large Garfield Park Apartment

$105

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Handsome Mccormick 3bd-2ba Loft

9.0

$184

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2 bedroom city pad in the heart of Pilsen

$194

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New! Stylish & Cozy 3bdrm, 10min/Ord, 20min/Dt

$157

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Close To Blue Line Train 15m Downtown 40 M O'hare Airport , Restaurants, Trail

$176

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Wrigleyville Unit - 1/2 block from Wrigley Field - sleeps 5

9.7

$249

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Lux 2B/1B Panoramic Views

$291

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Near Wrigley W/ 2 Balcony And Lake-View

$82

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343 West Wolf Point Plaza

$106

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1911 North Whipple Street apt. 2R

$72

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Old Town junior one bedroom #1R

$102

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Modern Condo Close to Cubs at Wrigley | Cubs | Netflix K2

$81

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Walk to Train and Beach| Minimalist-Style | Wrigley K6

$76

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Chic & Pristine 1BR for Couple, Great Location

8.8

$121

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New Super Host - Adorable Studio-Walk to Food

$73

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Music, Nightlife, Food & Train 7min to Wrigley M1

$68

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Comfy Apt,15min Uber To Cubs Convention, Wrigley M7

9.0

$71

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Convenient Studio | Fun, Food, Coffee, & Wrigley M9

$74

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Chicago - Living Large in Lincoln Square .02 to EL

$128

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Hyde Park Getaway

$116

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New ️ Pristine & Homey! Near Shopping District

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Vintage & Cozy Park view apartment- Free parking

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The Irving on Oakley

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When to book a vacation apartment in Chicago

Check out the tips below to find the best deal on a Chicago vacation rental property

Low Season	January
High Season	March

cheapest month to stay

40%

expected price decrease

most expensive time to stay

44%

expected price increase

Price

$146 - $431

Highest day of week	Friday
Cheapest day of week	Sunday

av. price over the last two weeks

Average price (weeknight)

$281

av. price over the last two weeks

Average price (weekend night)

$219

av. price over the last two weeks

Cheapest vacation rentals in Chicago

Our lowest priced vacation apartments and property rentals for a cheaper way to stay in Chicago

Ginosi 747 Apartel

$75

Oakwood 200 Squared

10.0

$116

Loop Suites

6.8

$80

Pilsen Roadhouse

8.0

$119

Pittsfield Apartments + Suites

6.6

$91

A Duplex for your Grouplex

$135

Chicago vacation apartments & rental properties FAQ

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

About 2 nights is the most common choice for those booking vacation apartment rentals in Chicago.

How much does a vacation rental apartment in Chicago cost?

The price of a vacation apartment in Chicago depends on the number of guests, locations and required amenities - for a standard apartment in Chicago you can expect to pay around $168 per night.

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

Chicago vacation rentals are at their cheapest in January. Rental prices can be around 40% lower per night than in the high season.

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

When looking for vacation apartments in Chicago, recent bookings have shown Hyde Park and Lincoln Park to be the most popular places to stay, with Logan Square also being increasingly considered.