Chicago vacation rentals
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Top-rated vacation rentals in Chicago
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Popular amenities for Chicago vacation rentals
Chicago fishing vacation rentals
Apartment in Chicago
4.85 out of 5 average rating, 159 reviewsYour brand new Chicago suite (unit 1F)
Jun 13 – 20
Apartment in Uptown
4.96 out of 5 average rating, 264 reviewsCozy loft in Chicago's Uptown
Oct 1 – 8
Guest suite in Evanston
4.97 out of 5 average rating, 213 reviewsA guest suite centrally located, but so quiet...
Aug 13 – 20
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Mar 28 – Apr 4
Condo in East Rogers Park
4.93 out of 5 average rating, 183 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Dec 11 – 18
Guest suite in Carol Stream
4.94 out of 5 average rating, 282 reviewsHot Tub, Pool Table, Bar, fishing & Kayak on Lake!
Apartment in Chicago
4.83 out of 5 average rating, 392 reviewsLakeview Charmer -with parking!
Mar 18 – 25
Apartment in Chicago
4.96 out of 5 average rating, 121 reviewsCozy 2 bdrm near McCormick Place & Wintrust Arena
Jun 9 – 16
Chicago apartment rentals
Apartment in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
Mar 30 – Apr 6
Apartment in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
Sep 10 – 17
Apartment in Humboldt Park
4.98 out of 5 average rating, 105 reviewsHumboldt Park Loft
Sep 4 – 11
Apartment in Chicago
4.98 out of 5 average rating, 296 reviewsRedesigned Lower Level Studio in Historic Building
Sep 23 – 30
Apartment in Chicago
4.95 out of 5 average rating, 103 reviewsComfortable, modern apartment 20 Min from Downtown
Feb 3 – 10
Apartment in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
Feb 4 – 11
Apartment in Chicago
4.82 out of 5 average rating, 434 reviewsLovely Andersonville Apt with Ideal Location
Jan 1 – 8
Apartment in Logan Square
4.9 out of 5 average rating, 282 reviewsModern Logan Square Apartment, steps from train!
Jan 6 – 13
Chicago house rentals
Home in West Town
4.95 out of 5 average rating, 169 reviewsParadise on the Park
Nov 26 – Dec 3
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
Sep 4 – 11
Home in Chicago
4.97 out of 5 average rating, 318 reviewsCozy garden apartment historic Jackson Bvld.
Oct 20 – 25
Home in Chicago
4.95 out of 5 average rating, 117 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Mar 22 – 29
Home in Chicago
4.96 out of 5 average rating, 313 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Jan 19 – 26
Home in Chicago
4.98 out of 5 average rating, 203 reviewsWrigleyville Southport Studio
Dec 28 – Jan 4
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Dec 20 – 27
Home in Whiting
4.8 out of 5 average rating, 225 reviewsWhiting Getaway
Apr 22 – 29
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 5,870 apartment rentals, over 1,100 condo rentals to over 1,830 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 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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