Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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Other great vacation rentals in Chicago
Apartment in Chicago
4.85 out of 5 average rating, 160 reviewsYour brand new Chicago suite (unit 1F)
Home in Chicago
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 9 – 16
Condo in East Rogers Park
4.93 out of 5 average rating, 186 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Jan 7 – 14
Apartment in Evanston
4.97 out of 5 average rating, 406 reviewsCharming, Sunny Apartment with Backyard Garden
Feb 12 – 19
Apartment in Chicago
4.92 out of 5 average rating, 396 reviewsAndersonville Living
Oct 3 – 10
Condo in Chicago
4.99 out of 5 average rating, 561 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Apartment in Bronzeville
4.95 out of 5 average rating, 123 reviewsCozy 2 bdrm near McCormick Place & Wintrust Arena
Jul 9 – 16
Townhouse in Chicago
4.98 out of 5 average rating, 228 reviewsBeautiful Lincoln Park/ De Paul Complimentary Parking Permit
Feb 11 – 18
Vacation rentals with pools in Chicago
Guest suite in Bartlett
4.96 out of 5 average rating, 185 reviewsCozy & Spacious Suite in Quiet Neighborhood
Dec 5 – 12
Apartment in Chicago
4.86 out of 5 average rating, 154 reviewsStunning Panoramic Chicago Views & Free Parking
Jan 16 – 23
Apartment in Chicago
4.89 out of 5 average rating, 462 reviewsWhole Flat in Private Club. Walk to L, Dining & Shows
Nov 30 – Dec 7
Apartment in The Loop
4.78 out of 5 average rating, 156 reviewsBeautiful Corner 2 Bedroom in the Loop | Roof Deck
Feb 5 – 12
Apartment in Chicago
4.87 out of 5 average rating, 110 reviewsLevel ◆ Two Bedroom Deluxe Corner Suite + Balcony
Jan 16 – 23
Condo in The Loop
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 10 – 17
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Sep 30 – Oct 7
Apartment in Itasca
4.77 out of 5 average rating, 181 reviewsKing Bed at Chicago Northwest + PET Friendly
Sep 27 – Oct 4
Chicago apartment rentals
Apartment in Chicago
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
Oct 23 – 30
Apartment in Chicago
4.93 out of 5 average rating, 191 reviewsQuirky Designer Apartment - Steps from Wrigley!
Jan 14 – 21
Apartment in Chicago
4.96 out of 5 average rating, 321 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Sep 30 – Oct 7
Apartment in Lincoln Square
4.78 out of 5 average rating, 269 reviewsCozy Garden-Subterranean Apartment
Sep 26 – Oct 3
Apartment in Chicago
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Sep 23 – 30
Apartment in Logan Square
4.91 out of 5 average rating, 370 reviewsThe Grotto of Logan Square
Sep 3 – 8
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Nov 7 – 14
Apartment in Chicago
4.98 out of 5 average rating, 128 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 9 – 16
Quick stats about vacation rentals in Chicago
Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K 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.
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 1,830 house rentals, over 5,870 apartment rentals to over 1,100 condo 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 rentals with a dedicated workspace in Chicago?
Yes! Work meets play with ease at over 6,560 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.
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