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Chicago vacation rentals

Book unique homes, 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.

Superhost
Apartment in Wicker Park
Newly remodeled 1BR! Only 5 MIN walk to BLUE LINE!
Located in the heart of Wicker Park, just a 5 min walk to the Damen blue line stop. This phenomenal location allows you to access EVERYTHING Chicago has to offer without having to rent a car. Experience the best of Chicago, all within a short walk from your stay. World class bars, restaurants, and shopping all within walking distance. Want to explore downtown or catch a Cubs game at Wrigley? Hop on the "L" train and use the CTA to go anywhere in the city. This cozy garden apartment has it all.
$118 per night
Superhost
Loft in Lake View
Lakeview Loft-Vintage Chicago, Modern Amenities
The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.
$126 per night
Superhost
Home in Chicago
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
$99 per night

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
Wrigley Field1,004 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Magnificent Mile597 locals recommend

Chicago fishing vacation rentals

Superhost
Apartment in Chicago
Spectacular Penthouse Corner 2BR in Streeterville
$154 per night
Superhost
Apartment in Chicago
Beautiful 2BR Apt in Old Town! Great Location!
$94 per night
Superhost
Condo in Chicago
❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
$157 per night
Superhost
Apartment in Chicago
Lincoln Pk-parking-wifi-King bd-crib-kid friendly
$169 per night
Superhost
Condo in Chicago
The Bright Retreat in Andersonville
$98 per night
Superhost
Apartment in East Rogers Park
LAKESIDE PIED `A TERRE STEPS TO BEACH
$125 per night
Superhost
Loft in Lake View
Urban Chicago Loft, 1 blk to train w/ 2 pkg spots
$166 per night
Superhost
Apartment in Uptown
Cozy loft in Chicago's Uptown near CTA/Red Line
$121 per night
Superhost
Apartment in Chicago
Archways at the Lincoln Park Zoo 2bed/2ba
$205 per night
Superhost
Condo in Gold Coast
MAG MILE 2/2 w/ Lake VIEWS! (+Rooftop)
$185 per night
Superhost
Guest suite in Andersonville
Cozy Andersonville Cabin
$125 per night
Superhost
Townhouse in Chicago
Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
$179 per night

Chicago apartment rentals

Superhost
Apartment in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
$119 per night
Superhost
Apartment in Wicker Park
Private Studio Apt in the Heart of Wicker Park!
$99 per night
Superhost
Apartment in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$38 per night
Superhost
Apartment in Lincoln Park
Lincoln Pk-Kingbd-fast WiFi-parking-crib/Highchair
$169 per night
Superhost
Apartment in Lincoln Park
Sophisticated Flat in Historic Building
$160 per night
Superhost
Apartment in Oak Park
Cosmopolitan Nest in Oak Park North Side
$70 per night
Superhost
Apartment in Andersonville
Lovely Andersonville Apt with Ideal Location
$93 per night
Superhost
Apartment in West Town
Explore the City from an Elegant, Urban Retreat
$123 per night
Superhost
Apartment in West Town
Ukrainian Village Garden Retreat
$125 per night
Superhost
Apartment in Chicago
Lincoln Paradise– Steps to Park & Zoo!
$108 per night
Superhost
Apartment in Chicago
Cozy Small Private Garden Apt in Chicago Logan Sq
$92 per night
Superhost
Apartment in Chicago
Cozy and Comfy 1BR Apartment in Logan Square!
$75 per night

Chicago homes

Superhost
Home in West Loop
Pro Cleaned & Isolated West Loop Coach House
$76 per night
Superhost
Home in West Town
Paradise on the Park
$123 per night
Superhost
Home in Chicago
Modern Home RoscoeVillage/Wrigley Free St Parking
$77 per night
Superhost
Home in Chicago
Cool Quiet Coach House W/ Private Access and Outdoor Space
$204 per night
Superhost
Home in Chicago
City Oasis Private Home HD Projector
$214 per night
Superhost
Home in Lake View
Wrigleyville Garden Studio
$139 per night
Superhost
Home in Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
$80 per night
Superhost
Home in West Loop
Cozy garden apartment historic Jackson Bvld.
$154 per night
Superhost
Home in Lincoln Park
Lincoln Park - DePaul House w/Patio Free Parking
$181 per night
Superhost
Home in Chicago
Private 3rd Floor Apartment
$140 per night
Superhost
Home in Portage Park
The Evergreen House
$95 per night
Superhost
Home in Blue Island
Warm and comfortable inviting Suburban home !
$89 per night

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.

Frequently Asked Questions

  • How is the weather in Chicago?

    Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.

  • What are some of the best things to do in Chicago?

    In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.

  • What is the best time of year to visit Chicago?

    Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.

  • What are the best places to stay in Chicago?

    Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.

  • What are the best places to visit in Chicago?

    Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.

  • What are some hiking trails in Chicago?

    While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.

  • What are some family activities to do in Chicago?

    Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.

  • What are some of the best day trip ideas in Chicago?

    For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.

  • What types of vacation rentals are available in Chicago?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 1,170 condo rentals, over 5,740 apartment rentals to over 1,800 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation home rentals with a dedicated workspace in Chicago?

    Yes! Work meets play with ease at over 10 vacation home rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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