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
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
Jul 12 – 19
G$25,425 GYD per night
5.0 out of 5 average rating, 287 reviews
Guest favorite
Apartment in Humboldt Park
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.
Jul 12 – 19
G$18,681 GYD per night
4.98 out of 5 average rating, 102 reviews
Guest favorite
Tiny home in Burr Ridge
Less is more! Pet friendly Tiny Home near Chicago!
Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome
Apr 7 – 14
G$24,845 GYD per night
4.92 out of 5 average rating, 216 reviews

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
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Chicago house rentals

Guest favorite
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
Nov 27 – Dec 2
G$32,854 GYD per night
4.97 out of 5 average rating, 315 reviews
Guest favorite
Home in Chicago
Wrigleyville Southport Studio
Oct 22 – 29
G$28,788 GYD per night
4.98 out of 5 average rating, 200 reviews
Guest favorite
Home in Chicago
Chicago Riverhouse private chill patio comfy beds
Sep 16 – 23
G$55,233 GYD per night
4.96 out of 5 average rating, 122 reviews
Guest favorite
Home in West Town
Paradise on the Park
Aug 7 – 14
G$30,821 GYD per night
4.94 out of 5 average rating, 163 reviews
Superhost
Home in Chicago
Lincoln Park - DePaul House w/Patio Free Parking
Mar 3 – 10
G$30,495 GYD per night
4.82 out of 5 average rating, 125 reviews
Guest favorite
Home in Berwyn
Private apartment with retro vibe
Jul 25 – Aug 1
G$19,318 GYD per night
4.92 out of 5 average rating, 226 reviews
Guest favorite
Home in Chicago
The Avondale Guesthouse
Feb 6 – 13
G$14,327 GYD per night
4.86 out of 5 average rating, 212 reviews
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
May 23 – 30
G$25,219 GYD per night
4.9 out of 5 average rating, 216 reviews
Guest favorite
Home in Uptown
Private 3rd Floor Apartment
Apr 28 – May 5
G$26,815 GYD per night
4.89 out of 5 average rating, 330 reviews
Guest favorite
Home in Chicago
Division St Designer Home In Heart of Wicker Park
May 2 – 9
G$66,216 GYD per night
4.96 out of 5 average rating, 193 reviews
Guest favorite
Home in Chicago
Spacious Two Story Luxurious Home w/Outdoor Deck!
Jan 28 – Feb 4
G$62,966 GYD per night
4.92 out of 5 average rating, 108 reviews
Guest favorite
Home in Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
Oct 19 – 26
G$25,748 GYD per night
4.95 out of 5 average rating, 303 reviews

Chicago condo rentals

Superhost
Condo in Chicago
-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Mar 29 – Apr 5
G$14,509 GYD per night
4.81 out of 5 average rating, 124 reviews
Superhost
Condo in Chicago
Humboldt Park Traveler's Lodge
Mar 17 – 24
G$16,768 GYD per night
4.87 out of 5 average rating, 431 reviews
Guest favorite
Condo in Chicago
Pvt 1bdr Rogers Park, Loyola, Northwestern.
Dec 24 – 31
G$21,754 GYD per night
4.94 out of 5 average rating, 176 reviews
Superhost
Condo in Chicago
Spacious Duplex in Great Location
Apr 18 – 25
G$18,529 GYD per night
4.87 out of 5 average rating, 101 reviews
Guest favorite
Condo in Chicago
Great location. Free parking.
Apr 7 – 12
G$20,926 GYD per night
4.97 out of 5 average rating, 690 reviews
Guest favorite
Condo in Chicago
Unique Lincoln Park Duplex Apt
May 2 – 9
G$33,482 GYD per night
4.95 out of 5 average rating, 429 reviews
Guest favorite
Condo in Chicago
Lincoln Square Gem!
May 6 – 13
G$29,905 GYD per night
4.98 out of 5 average rating, 325 reviews
Guest favorite
Condo in Chicago
Near Lake Michigan & Wrigley Field
Jun 25 – Jul 2
G$51,792 GYD per night
4.98 out of 5 average rating, 187 reviews
Guest favorite
Condo in Chicago
Updated Designer Duplex In Fulton Market W/parking
Dec 11 – 18
G$138,112 GYD per night
4.95 out of 5 average rating, 165 reviews
Guest favorite
Condo in Chicago
Private hot tub - King bed suite - Free parking
Jul 6 – 13
G$65,594 GYD per night
4.96 out of 5 average rating, 108 reviews
Guest favorite
Condo in Chicago
Urban Comfort in the Heart of Chicago
Jun 5 – 12
G$46,037 GYD per night
4.99 out of 5 average rating, 550 reviews
Guest favorite
Condo in Chicago
Susie's Space. 2BR easy parking & pet friendly
May 19 – 24
G$26,451 GYD per night
4.9 out of 5 average rating, 293 reviews

Chicago apartment rentals

Guest favorite
Apartment in Chicago
The Grotto of Logan Square
Apr 14 – 19
G$17,787 GYD per night
4.9 out of 5 average rating, 366 reviews
Superhost
Apartment in Chicago
LAKESIDE PIED `A TERRE STEPS TO BEACH
Apr 16 – 23
G$21,500 GYD per night
4.89 out of 5 average rating, 101 reviews
Guest favorite
Apartment in Chicago
Charming Edgewater/Andersonville Garden 1 bdrm.
Jan 13 – 20
G$18,346 GYD per night
4.93 out of 5 average rating, 194 reviews
Guest favorite
Apartment in Chicago
Logan Square Studio
Oct 27 – Nov 3
G$18,091 GYD per night
4.87 out of 5 average rating, 477 reviews
Guest favorite
Apartment in Chicago
Modern Apt with style & comfort in Pilsen Chicago
G$17,549 GYD per night
4.98 out of 5 average rating, 117 reviews
Guest favorite
Apartment in Skokie
Cozy Garden Unit in Quiet Neighborhood
Dec 21 – 28
G$22,750 GYD per night
4.91 out of 5 average rating, 520 reviews
Guest favorite
Apartment in Lincoln Square
Bright family-friendly Lincoln Square 2-bed 1-bath
Oct 17 – 24
G$24,089 GYD per night
4.96 out of 5 average rating, 312 reviews
Guest favorite
Apartment in Chicago
Amazing Location | Stunning Views | Free Parking
Dec 12 – 19
G$73,839 GYD per night
4.86 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Chicago
Spacious 2BR on Quiet St - Free Park/Late Checkout
Oct 19 – 26
G$32,250 GYD per night
4.98 out of 5 average rating, 190 reviews
Guest favorite
Apartment in Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
Oct 30 – Nov 6
G$18,886 GYD per night
4.96 out of 5 average rating, 232 reviews
Guest favorite
Apartment in Chicago
Cozy loft in Chicago's Uptown
May 6 – 13
G$21,907 GYD per night
4.96 out of 5 average rating, 257 reviews
Guest favorite
Apartment in Chicago
Urban Chic Apartment by the Magnificent Mile
Nov 1 – 8
G$46,037 GYD per night
4.94 out of 5 average rating, 210 reviews

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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