Skip to content

Chicago vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chicago

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

Rental unit in Lake View
Beautiful|Cozy 1BR 1BA in Lakeview - BelmontHarbor
Experience Chicago at its best by staying at this spacious and cozy apartment. This place gives a peaceful and modern feel making it a place you'll never want to leave. We are located in a quiet and friendly neighborhood which is close to various restaurants, cafes, and shopping centers. Enjoy being close to Lincoln Park Zoo, Millenium Park and other historic museums nearby. Getting around is easy with accessible public transport and only 3 minutes away from multiple train stations.
$96 per night
SUPERHOST
Rental unit in The Loop
*CHI-City Getaway- Expanding Views!*
Enjoy a comfortable experience at this centrally-located place. Walking distance from Millennium Park & Solider Field. Close to McCormick for all your conference and events to attend! Apartment is filled with everything you may need! Just come with your bags and enjoy a beautiful stay with views of the Willis Tower. Hungry? Say no more, restaurants are right outside of your stay. Close drive or public transportation to West Loop, River North, Wicker Park, and more!
$188 per night
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
Freehand Hotel is great for couples, solo adventurers, and business travelers. Experience the comfortable and casual vibe designed by Roman & Williams in River North Chicago, just two blocks from the Magnificent Mile. Walking distance to public transportation, Navy Pier, and more. $10 nightly resort fee plus tax paid at the property For long-term stays, guests must move rooms about every 30 days.
$109 per night

Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park1,243 locals recommend
Photo of Navy Pier
Navy Pier927 locals recommend
Photo of Wrigley Field
Wrigley Field1,004 locals recommend
Photo of Lincoln Park
Lincoln Park175 locals recommend
Photo of Grant Park
Grant Park332 locals recommend
Photo of United Center
United Center199 locals recommend

Downtown Chicago vacation rentals

Condo in Logan Square
Wicker Park/Bucktown condo w/outdoor patio /APT 1
$129 per night
SUPERHOST
Condo in Wicker Park
Modern Izakaya Studio in Wicker Park
$141 per night
SUPERHOST
Rental unit in Lake View
Stylish|Cozy Getaway in Lakeview|1BR|3min~Wrigley
$84 per night
SUPERHOST
Private room in River North
Chicago Speakeasy-Style Loft Suite (Room 1B)
$121 per night
SUPERHOST
Rental unit in Chicago
McCormick Place Studio/parking/sleeps up to 4
$141 per night
SUPERHOST
Rental unit in Chicago
Sonder South Wabash | Studio Apt w/ City View
$146 per night
Hotel room in The Loop
Charming King Bedroom in Loop
$127 per night
SUPERHOST
Condo in Little Italy
Private hot tub - King bed suite - Free parking
$182 per night
SUPERHOST
Rental unit in Lincoln Square
Warm|Cozy|Lovely|1BR|Lincoln Sq.|
$76 per night
SUPERHOST
Private room in Lake View
Private room with private entrance in Boystown
$64 per night
SUPERHOST
Rental unit in Irving Park
Private Entrance|Free Parking Space|2BR|Lincoln Sq
$116 per night
SUPERHOST
Rental unit in Gold Coast
MAG MILE Luxe Designer Apartment - Steps to Lake!
$79 per night
SUPERHOST

Chicago summer vacation rentals

Rental unit in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
$130 per night
SUPERHOST
Rental unit in Lincoln Square
✨Hidden Gem|Trendy|1BR|Vibrant Lincoln Sq. ✨
$117 per night
SUPERHOST
Rental unit in Uptown
Modern studio at Uptown by Red Line,Aragon,Riviera
$72 per night
SUPERHOST
Rental unit in Lake View
Beautiful Belmont 1BR Apt w/ In-Unit Washer/Dryer
$66 per night
Hotel room in The Loop
Spacious Hotel Room in The Loop
$127 per night
SUPERHOST
Rental unit in Chicago
Sonder South Wabash | Superior 1BR Apt w/ Balcony
$240 per night
Condo in Chicago
McCormick Place Studio/parking/sleeps up to 4
$146 per night
SUPERHOST
Rental unit in Wicker Park
COZY Bright*BOLD*FUN* Eclectic Wicker Park Home
$125 per night
SUPERHOST
Rental unit in Near North Side
Kasa | Explore the Neighborhood-Mag Mile | Chicago
$130 per night
Private room in Lake View
Bright Room with a Garden View
$41 per night
SUPERHOST
Rental unit in Lake View
*Chic|Cozy|Entire 2Bd Short walk to Wrigley Field*
$111 per night
SUPERHOST
Rental unit in Chicago
McCormick Place Studio/parking/sleeps up to 4
$141 per night
SUPERHOST

Chicago holiday vacation rentals

Rental unit in River North
1BR Luxury Apartment With Private Office, Terrace,
$237 per night
Rental unit in Lake View
Alluring & Secure Studio, Wi-Fi & NO Cleaning Fee!
$67 per night
Hotel room in The Loop
Private King Room in Theatre District
$127 per night
SUPERHOST
Rental unit in Chicago
McCormick 420 friendly 2br/2ba parking/sleeps 6
$186 per night
SUPERHOST
Rental unit in Lincoln Square
Spacious, light-drenched studio-private entrance!
$109 per night
SUPERHOST
Rental unit in Lombard
Modern 1-Bedroom *Comfy Queen Bed*
$117 per night
Rental unit in Wicker Park
Pierce Place
$87 per night
Rental unit in Lincoln Park
NEW 1-bedroom rental with fire place
$99 per night
Rental unit in Uptown
Cozy 1 bdr in Ravenswood,close to Wrigley|Downtown
$85 per night
SUPERHOST
Rental unit in Uptown
Vibrant studio at Uptown by Red Line (02)
$68 per night
SUPERHOST
Rental unit in Lake View
Lux 1BR/1BA Apartment in Belmont
$76 per night
Rental unit in Magnificent Mile
☀️Amazing Gold Coast Apt w/ Rooftop Pool & Gym☀️
$168 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