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Chicago vacation rentals

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Top-rated vacation rentals in Chicago

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Apartment in Chicago
Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
Jul 25 – Aug 1
$100 per night
Guest favorite
Apartment in Chicago
Designer Avondale Attic
Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.
May 5 – 12
$90 per night
Guest favorite
Apartment in Chicago
Humboldt Park Loft
Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.
Aug 12 – 19
$89 per night

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Magnificent Mile597 locals recommend
Shedd Aquarium673 locals recommend

Chicago house rentals

Guest favorite
Home in Berwyn
Private apartment with retro vibe
Apr 30 – May 7
$86 per night
Guest favorite
Home in Uptown
Private 3rd Floor Apartment
Feb 10 – 17
$98 per night
Guest favorite
Home in Avondale
The Avondale Guesthouse
Jan 12 – 19
$67 per night
Guest favorite
Home in Chicago
Paradise on the Park
Mar 9 – 16
$133 per night
Guest favorite
Home in Chicago
Wrigleyville Southport Studio
Jul 26 – Aug 2
$139 per night
Guest favorite
Home in Chicago
Greystone Haven in Logan Square
Apr 13 – 20
$157 per night
Guest favorite
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
Dec 8 – 13
$145 per night
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
May 5 – 12
$119 per night
Guest favorite
Home in Chicago
Division St Designer Home In Heart of Wicker Park
Mar 25 – Apr 1
$200 per night
Guest favorite
Home in Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
Nov 30 – Dec 7
$124 per night
Guest favorite
Home in Chicago
Chicago Riverhouse comfy beds nestled in nature
Jul 17 – 24
$292 per night
Guest favorite
Home in Chicago
Cozy & Modern Chic Full House in Trendy Bridgeport
Dec 18 – 25
$106 per night

Chicago condo rentals

Guest favorite
Condo in Chicago
Great location. Free parking.
Mar 3 – 8
$94 per night
Superhost
Condo in Chicago
Humboldt Park Traveler's Lodge
Mar 17 – 24
$87 per night
Superhost
Condo in Chicago
-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Mar 29 – Apr 5
$69 per night
Guest favorite
Condo in Chicago
Unique Lincoln Park Duplex Apt
Sep 9 – 16
$160 per night
Guest favorite
Condo in Chicago
Near Lake Michigan & Wrigley Field
Mar 3 – 10
$178 per night
Guest favorite
Condo in Chicago
Lincoln Square Gem!
May 5 – 12
$141 per night
Superhost
Condo in Chicago
Private studio with free garage parking
$83 per night
Guest favorite
Condo in Chicago
Private hot tub - King bed suite - Free parking
Jun 29 – Jul 6
$317 per night
Guest favorite
Condo in East Rogers Park
Pvt 1bdr Rogers Park, Loyola, Northwestern.
Jan 29 – Feb 5
$101 per night
Guest favorite
Condo in Chicago
Sunny Tri Level
May 12 – 19
$273 per night
Guest favorite
Condo in Chicago
Urban Comfort in the Heart of Chicago
Jun 10 – 17
$201 per night
Guest favorite
Condo in Chicago
East Lakeview Designer Condo with 2 Bd, 2 Bath
Feb 17 – 24
$279 per night

Chicago apartment rentals

Guest favorite
Apartment in Chicago
Charming Edgewater/Andersonville Garden 1 bdrm.
Oct 21 – 28
$88 per night
Guest favorite
Apartment in Chicago
Gorgeous Studio 15 Minutes From Ohare!
Jan 21 – 28
$74 per night
Guest favorite
Apartment in Chicago
Charming Gold Coast One-Bedroom Near Downtown!
Feb 5 – 12
$90 per night
Guest favorite
Apartment in Chicago
Amazing Location | Stunning Views | Free Parking
Feb 4 – 11
$353 per night
Guest favorite
Apartment in Lincoln Square
Bright family-friendly Lincoln Square 2-bed 1-bath
Oct 13 – 20
$115 per night
Guest favorite
Apartment in Chicago
Bright, Modern Apartment in a Vintage Greystone
Jan 17 – 24
$122 per night
Guest favorite
Apartment in Berwyn
Berwyn Betty Apartment
Jul 25 – Aug 1
$115 per night
Guest favorite
Apartment in Chicago
Modern Apt with style & comfort in Pilsen Chicago
$65 per night
Superhost
Apartment in Chicago
The Cottage
$74 per night
Guest favorite
Apartment in Oak Park
Cosmopolitan Nest in Oak Park North Side
Aug 7 – 14
$63 per night
Guest favorite
Apartment in Chicago
Renovated Designer Apartment in Heart of Lincoln Square
Apr 23 – 30
$105 per night
Guest favorite
Apartment in Chicago
Charming renovated Victorian apartment in Old Town
Mar 1 – 8
$119 per night

Quick stats about vacation rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K reviews

Your guide to Chicago

All About Chicago

Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.

You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.


The best time to stay in a vacation rental in Chicago

Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.


Top things to do in Chicago

The Art Institute of Chicago

The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.

Willis Tower

The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.

Millennium Park

Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.

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