Skip to content

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 in Humboldt Park
Fashionable Room w/ full bathroom - FREE PARKING!
Secluded, beautifully designed private room with key code access and full private bathroom. The spacious 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, as well as a SmartTV with complimentary Netflix. Convenient location close to the famous 606 Trail, and Humboldt Park, itself. Comes with a free parking spot in the building's garage!
$58 per night
SUPERHOST
Rental unit in West Town
Great location! Spacious & private! Free parking
Tough to beat this location (River West), accessible to everything via public transportation, great spots walkable from your door & free street parking nearby! Spacious open floor plan provides you a quiet escape from the excitement of the city! It's very comfortable & well designed for a perfect visit! Steps to local dining, great coffee, brewery, cocktails & so much more. Get to almost all popular spots in Chicago in 5-10 minutes! 3 minute walk to the Chicago blue line, 56 & 66 bus lines.
$170 per night
SUPERHOST
Private room in Englewood
Comfy Bedroom unit 2 | room # 1 – 25min Downtown
A place you can come to and make memories. Hop on the CTA for a quick ride downtown, 20 minutes, to enjoy shopping and family friendly activities. You can also stay in to relax and enjoy coffee, tea, or hot chocolate at the self serve coffee bar. For a little more in house excitement, hang out in the photo / game room and have fun playing 2,000+ arcade games. You can also enjoy the Smart Tv to binge-watch all your favorite shows on Netflix. The perfect Airbnb for your next Chicago getaway.
$45 per night
SUPERHOST

Stay near Chicago's top sights

Photo of Navy Pier
Navy Pier933 locals recommend
Photo of Wrigley Field
Wrigley Field1,004 locals recommend
Photo of Lincoln Park
Lincoln Park175 locals recommend
Photo of O'Hare International Airport
O'Hare International Airport122 locals recommend
Photo of Shedd Aquarium
Shedd Aquarium673 locals recommend
Photo of Magnificent Mile
Magnificent Mile598 locals recommend

Chicago summer vacation rentals

Private room in Hyde Park
Fresh and Sunny Bed & Bath by UofC
$81 per night
SUPERHOST
Rental unit in Uptown
Vibrant studio at Uptown by Red Line (02)
$112 per night
SUPERHOST
Private room in Irving Park
West Wing at the Kilbourn House
$64 per night
SUPERHOST
Private room in Irving Park
Remote Workers Dream - Private Bath and Workspace
$66 per night
SUPERHOST
Private room in Roscoe Village
NEW,Roscoe Village,Cubs, Pvt Bath, Pvt Entrance
$85 per night
SUPERHOST
Private room in Humboldt Park
Spacious PRVT Room w/ Full Bathroom - Logan Square
$51 per night
SUPERHOST
Condo in Wicker Park
Modern Izakaya Studio in Wicker Park
$194 per night
SUPERHOST
Rental unit in West Town
Cute Designer Touch Loft, Skylights, Blue Line
$141 per night
Private room in Pilsen Historic District
BOHEMIAN LODGE #1 (clean & affordable travel)
$66 per night
SUPERHOST
Private room in Irving Park
East Wing at the Kilbourn House
$69 per night
SUPERHOST
Rental unit in Logan Square
Remodeled Boho 1 Bedroom in Hip Logan Square
$133 per night
SUPERHOST
Rental unit in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
$174 per night
SUPERHOST

Downtown Chicago vacation rentals

Rental unit in Andersonville
Lovely Andersonville Apt with Ideal Location
$140 per night
SUPERHOST
Rental unit in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$98 per night
PLUS
Private room in Englewood
Living in a dream (unit 2 room #5)
$49 per night
SUPERHOST
Private room in Humboldt Park
Chic PRVT Room w/ Full Bathroom | Logan Square
$51 per night
SUPERHOST
Condo in Uptown
Vibrant studio at Uptown close to RedLine
$125 per night
SUPERHOST
Private room in Pilsen Historic District
BOHEMIAN LODGE #2 (clean & affordable travel)
$65 per night
SUPERHOST
Private room in Lake View
Great Location / Private Room in Lakeview
$60 per night
SUPERHOST
Private room in Lake View
Contemporary, private suite w fireplace
$64 per night
SUPERHOST
Rental unit in Wicker Park
Stylish First Flr. Studio. Best Location Division+Hermitage.
$153 per night
PLUS
Private room in Edgewater
Spacious & Relaxing Loft in Awesome Andersonville!
$90 per night
SUPERHOST
Private room in East Garfield Park
Large bedroom near medical district and UIC
$37 per night
Private room in Norwood Park
Private Room By O’hare And Public Transport
$35 per night
SUPERHOST

Chicago holiday vacation rentals

Private room in Pilsen Historic District
Sunny full floor (Sleeps 4+ guests)
$66 per night
SUPERHOST
Rental unit in Lincoln Square
Warm|Cozy|Lovely|1BR|Lincoln Sq.|
$140 per night
SUPERHOST
Rental unit in Little Italy
UIC / Little Italy - Lovely 1 Bed 1 Bath Apt.
$130 per night
SUPERHOST
Private room in West Town
🌟 Cozy Bedroom by Downtown & Train; Rooftop Deck!🌟
$55 per night
SUPERHOST
Rental unit in Lincoln Park
Elegant Depaul Apt on Jonquil Park
$122 per night
SUPERHOST
Rental unit in Bridgeport
Bright Spacious Retreat in Trendy Bridgeport
$90 per night
SUPERHOST
Rental unit in Uptown
Charming Uptown Studio - Clean & Close to Train!
$87 per night
SUPERHOST
Condo in Lake View
Urban Comfort in the Heart of Chicago
$169 per night
SUPERHOST
Rental unit in Lincoln Park
Lincoln Park Studio, Great Value!
$112 per night
SUPERHOST
Rental unit in Uptown
Stylish studio at Uptown by Red Line
$109 per night
SUPERHOST
Private room in Englewood
Work from home beauty (unit 2 room #4)
$41 per night
SUPERHOST
Private room in Humboldt Park
Trendy PRVT Room w/ Full Bathroom | Logan Square
$51 per night
SUPERHOST

Stays in Downtown Chicago

Rental unit in Near North Side
Kasa | Explore the Neighborhood-Mag Mile | Chicago
$247 per night
Rental unit in Near North Side
51st Floor MagMile Penthouse Views Balcony Pool
$368 per night
SUPERHOST
Rental unit in Near North Side
50th Floor Mag Mile VIEWS, Balcony, Pool, Gym
$274 per night
SUPERHOST
Private room in River North
Chicago Speakeasy-Style Loft Space (Room 3A)
$110 per night
SUPERHOST

Stays in Lincoln Park

Rental unit in Lincoln Park
Sophisticated Flat in Historic Building
$262 per night
PLUS
Condo in Lincoln Park
Unique Lincoln Park Duplex Apt
$156 per night
SUPERHOST
Rental unit in Lincoln Park
Lincoln Pk-parking-wifi-King bd-crib-kid friendly
$254 per night
SUPERHOST
Rental unit in Lincoln Park
Rare, Updated 1 BR Condo in Lincoln Park!
$161 per night

Stays in Wrigleyville

Rental unit in Wrigleyville
Fabulous Wrigleyville/Boystown Oasis + Parking
$204 per night
SUPERHOST
Rental unit in Wrigleyville
'Secret Garden' Apartment in Wrigleyville
$171 per night
SUPERHOST
Rental unit in Wrigleyville
Stylish, posh, and very private flat
$111 per night
SUPERHOST
Rental unit in Lake View
Stylish|Cozy Getaway in Lakeview|1BR|3min~Wrigley
$207 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.

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago