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Chicago vacation rentals

Book unique condos, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Chicago

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

Private room · McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
You will enjoy a private bedroom in our home located in a family friendly neighborhood 8 min from Downtown Chicago. We are conveniently located 1 block away from the bus stop and 5 blocks away from the CTA (subway).
Mar 31 – Apr 7
$36 per night
Superhost
Private room · Humboldt Park
Spacious PRVT Room w/ Full Bathroom - Logan Square
Beautiful and spacious private room with full bathroom, and a queen-sized bed. The elegant and meticulously maintained interior is complemented by stylish furniture, charming brick wall and tasteful art. Enjoy your own workspace to catch up on e-mails or relax in the comfort of a queen-sized bed. Watch all your favorite shows on the SmartTV with complimentary Netflix. Convenient location close to the famous 606 Trail, and Humboldt Park, itself.
May 1 – 8
$79 per night
Superhost
Private room · Bridgeport
Private Room A5 by Chinatown
Recently renovated, perfect location for this place. Walking distance to Chinatown, minutes drive to Downtown. Main entrance is on the apartment first floor of Canal Street. Room A5 is all yours. It has mattress, comforter, sheets, towels and other basic needs. The internet is 800 mbps high speed internet. It is super fast and stable so you can do you online work easily or play some games. Check my other listings for more information. You will definitely find a room that works for you.
Nov 11 – 18
$31 per night

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park475 locals recommend
Photo of Navy Pier
Navy Pier307 locals recommend
Photo of Willis Tower
Willis Tower154 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago440 locals recommend
Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago191 locals recommend

Downtown Chicago vacation rentals

Private room · South Lawndale
Stylish, Shared Apartment for the Perfect Get Away
Jun 8 – 15
$30 per night
Superhost
Private room · Humboldt Park
Chic PRVT Room w/ Full Bathroom | Logan Square
Jul 13 – 20
$79 per night
Superhost
Private room · Chicago
City View near Downtown Chicago Sox Chinatown
Apr 22 – 29
$42 per night
Private room · Little Italy
Great Location Private Room-5 min to the City
Jun 4 – 11
$60 per night
Private room · Norwood Park
Private Bedroom By O’hare & Public Transport
Nov 1 – 8
$39 per night
Superhost
Private room · McKinley Park
Downtown Chicago 8 minutes away New Queen Bed
Feb 16 – 23
$41 per night
Superhost
Private room · Pilsen Historic District
BOHEMIAN LODGE #4 ( clean & affordable travel)
Dec 30 – Jan 6
$48 per night
Superhost
Private room · Woodlawn
Quiet Room #5
Feb 19 – 26
$35 per night
Superhost
Home · South Lawndale
2nd fl clean spacious ntflix 2bdr No pets no party
Mar 18 – 25
$56 per night
Private room · Bridgeport
Self Check-in 8 min Downtown Chicago
Jun 29 – Jul 6
$39 per night
Private room · Chicago
Egyptian Room - Free Parking, 1 block to CTA
Jan 2 – 9
$34 per night
Apartment · Pilsen Historic District
Teeny Tiny Bohemian Lodge - Clean & Affordable
Dec 2 – 9
$47 per night
Superhost

Chicago summer vacation rentals

Private room · Pilsen Historic District
In the heart of Pilsen, Self Check In
Dec 6 – 13
$50 per night
Superhost
Private room · Lake View
Queen Bed with Private Bathroom in Boystown
Nov 27 – Dec 4
$53 per night
Superhost
Private room · McKinley Park
SELF CHECK IN Downtown Chicago in 8 minutes
May 26 – Jun 2
$32 per night
Superhost
Private room · Norwood Park
Private Room By O’hare And Public Transport
Oct 25 – Nov 1
$39 per night
Superhost
Private room · Woodlawn
Quiet Room #3
Jan 7 – 14
$35 per night
Superhost
Private room · Chicago
New Queen bed near Chinatown Downtown Chicago
Feb 1 – 8
$46 per night
Private room · Lake View
Cute room in downtown Boystown
Nov 13 – 20
$45 per night
Superhost
Private room · Bridgeport
Luxury Stay near Downtown Chicago New Queen bed
Jun 3 – 10
$38 per night
Guesthouse · Oak Park
1 Bdrm Coach House - Frank Lloyd Wright District
Jan 29 – Feb 5
$86 per night
Apartment · Logan Square
Lovely Studio, 3min walk to train for Downtown/ORD
Feb 27 – Mar 6
$66 per night
Private room · Chicago
Mark Twain's Room
Mar 31 – Apr 7
$47 per night
Apartment · West Town
Cabin #208 at 747 Lofts
Jan 25 – Feb 1
$99 per night
Superhost

Chicago holiday vacation rentals

Apartment · Woodlawn
BEST In Chicago. Entire condo w/FREE Gated parking
Sep 18 – 25
$89 per night
Superhost
Private room · Lincoln Square
Basic accomodation equipped for short terms stays.
Jan 24 – 31
$54 per night
Superhost
Private room · McKinley Park
New Queen Bed near Downtown Chicago
Nov 29 – Dec 6
$43 per night
Superhost
Private room · Chicago
City View near Downtown Chicago Sox & Chinatown
Aug 22 – 29
$42 per night
Private room · Englewood
Cozy Chicago bedroom unit # 2 room # 3
Nov 3 – 10
$59 per night
Superhost
Apartment · Hyde Park
Historic Studio Near UChicago & DT by Zen Rentals
Feb 23 – Mar 2
$86 per night
Private room · Hyde Park
HydePark002, UC, NavyPier, Chinatown, freeparking
May 26 – Jun 2
$69 per night
Superhost
Private room · Woodlawn
Quiet Room #1
Aug 6 – 13
$35 per night
Superhost
Private room · Kenwood
Hyde Park/UC Newly Renovated Private Room #3
Mar 12 – 19
$44 per night
Superhost
Private room · Logan Square
Location, Location, Location, Private Bedroom
Sep 22 – 29
$47 per night
Private room · Forest Park
7C3eih1 Cozy Night's Stay - Small Cozy Room
Jul 15 – 22
$50 per night
Private room · Lincoln Square
Cozy Clean Large Private Room in Lincoln Square
Aug 1 – 8
$53 per night
Superhost

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.


When is 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.


What are the 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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