Chicago vacation rentals

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Top-rated vacation rentals in Chicago

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

Superhost
Guest suite in Chicago
Bike the Lakefront from a Sleek Urban Retreat
Cook in a stainless-steel kitchen with granite countertops, gleaming utensils, and a well-stocked fridge. Black and gray accents and dark woods offset a muted palette at this open-concept home. Thoughtful details include 800-thread-count linens. A retreat designed to evoke relaxation through luxury and elements of the earth. Lush bath linens & robes, luxury body and hair care products, coupled with sleek design creates a spa bathroom retreat you're sure to enjoy. Full granite and stainless steel kitchen, with wine fridge, stocked with morning essentials and Bronzeville BNB staples to ease you into the day's adventure. Relax or be social in the open space living and dining area equipped with Amazon entertainment system and Wi-Fi providing up-to-date weather, sports, news, the latest movies and yes...sometimes...work. Retreat to one of three sleeping accommodations, each drept in 800 thread count, 100% cotton linens. You'll find Bronzeville BNB thoughtful touches around every corner. Enjoy! You'll have access to the full suite including open floor plan living room/dining room/kitchen, spa bathroom, bedroom with walk in closet, hall closet, rear mud room containing washer/dryer, mop/broom, garbage tray, and fire extinguisher. There is concrete patios at the front and the rear entrances also. The backyard, main property deck and garage are restricted areas. The suite is nestled in the historic Bronzeville-Hyde Park neighborhood. Rent a Divvy bike to explore the 18-mile lakefront recreation trail close by. Chicago’s main attractions are a short drive away. The most efficient way to get around the city is UBER offering door-to-door service to all of Chicago's top attractions. Claim your FREE Uber ride (up to $5) gift from the host by signing up using this link: https://www.uber.com/invite/zkyf4 Divvy bike rentals are an awesome way to explore Chicago's 18 mile lakefront trail. The Divvy Explorer Pass includes 24 hours of bike access, with unlimited trips up to 3 hours each for $15/day. Pick up and return bikes at the 575+ Chicago & Evanston Divvy stations. Download the Divvy app for station locations and ride pass purchases. Your safety is important. Please be safe and aware of your surroundings. In any huge city, things can happen. It is suggested to not walk at night, avoid public transportation outside of downtown, and use rideshare transportation apps to avoid exchanging currency.
Dec 20 – 27
$100 per night
4.93 out of 5 average rating, 168 reviews
Guest favorite
Guest suite in Chicago
Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
Sep 2 – 9
$122 per night
5.0 out of 5 average rating, 290 reviews
Guest favorite
Apartment in Chicago
Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.
Sep 6 – 13
$99 per night
4.97 out of 5 average rating, 260 reviews

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Chicago homes

Guest favorite
Home in Chicago
Wrigleyville Southport Studio
Oct 27 – Nov 3
$138 per night
4.98 out of 5 average rating, 201 reviews
Guest favorite
Home in Chicago
Cozy garden apartment historic Jackson Bvld.
Nov 28 – Dec 3
$157 per night
4.97 out of 5 average rating, 315 reviews
Guest favorite
Home in Chicago
Cozy & Modern Chic Full House in Trendy Bridgeport
Dec 4 – 11
$104 per night
4.95 out of 5 average rating, 110 reviews
Guest favorite
Home in Chicago
Paradise on the Park
Oct 30 – Nov 6
$132 per night
4.95 out of 5 average rating, 164 reviews
Guest favorite
Home in Chicago
The Avondale Guesthouse
Dec 20 – 27
$98 per night
4.86 out of 5 average rating, 214 reviews
Guest favorite
Home in Chicago
Private 3rd Floor Apartment
Oct 22 – 29
$109 per night
4.89 out of 5 average rating, 331 reviews
Guest favorite
Home in Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
Dec 5 – 12
$122 per night
4.95 out of 5 average rating, 306 reviews
Guest favorite
Home in Berwyn
Private apartment with retro vibe
Aug 6 – 13
$83 per night
4.92 out of 5 average rating, 232 reviews
Guest favorite
Home in Blue Island
Warm and comfortable inviting Suburban home !
May 13 – 20
$97 per night
4.81 out of 5 average rating, 168 reviews
Guest favorite
Home in Chicago
Division St Designer Home In Heart of Wicker Park
Aug 25 – Sep 1
$462 per night
4.96 out of 5 average rating, 194 reviews
Guest favorite
Home in Forest Park
Charming dog friendly 2-Bath Bungalow Near Chicago
Jun 12 – 19
$124 per night
4.9 out of 5 average rating, 217 reviews
Guest favorite
Home in Chicago
The Evergreen House
May 10 – 17
$117 per night
4.98 out of 5 average rating, 175 reviews

Chicago condo rentals

Superhost
Condo in Chicago
Spacious Duplex in Great Location
May 10 – 17
$95 per night
4.87 out of 5 average rating, 102 reviews
Guest favorite
Condo in Chicago
Lincoln Square Gem!
Sep 1 – 8
$127 per night
4.98 out of 5 average rating, 325 reviews
Superhost
Condo in Chicago
Humboldt Park Traveler's Lodge
Apr 20 – 27
$107 per night
4.87 out of 5 average rating, 431 reviews
Superhost
Condo in Chicago
Private studio with free garage parking
Mar 26 – Apr 2
$103 per night
4.83 out of 5 average rating, 280 reviews
Superhost
Condo in Chicago
Near McCormick Place and Minutes from Downtown!
Jul 4 – 11
$133 per night
4.86 out of 5 average rating, 335 reviews
Guest favorite
Condo in Chicago
Pvt 1bdr Rogers Park, Loyola, Northwestern.
Sep 22 – 29
$107 per night
4.94 out of 5 average rating, 178 reviews
Superhost
Condo in Chicago
Cozy Apartment with Free On-Site Parking
Aug 29 – Sep 5
$109 per night
4.82 out of 5 average rating, 434 reviews
Superhost
Condo in Chicago
-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Apr 1 – 8
$67 per night
4.81 out of 5 average rating, 124 reviews
Guest favorite
Condo in Chicago
Spacious & Modern Family Friendly North Center Apt
Jan 18 – 25
$133 per night
4.91 out of 5 average rating, 116 reviews
Guest favorite
Condo in Evanston
2 bedroom apartment with patio and parking
Nov 24 – Dec 1
$119 per night
4.82 out of 5 average rating, 104 reviews
Guest favorite
Condo in Chicago
Modern/Spacious 2BR/2BA West Town
Dec 21 – 28
$146 per night
4.91 out of 5 average rating, 232 reviews
Guest favorite
Condo in Chicago
3D Tour! Designer Condo near Logan Square
Jul 18 – 25
$122 per night
4.87 out of 5 average rating, 115 reviews

Chicago apartment rentals

Guest favorite
Apartment in Chicago
Modern Apt with style & comfort in Pilsen Chicago
$75 per night
4.98 out of 5 average rating, 118 reviews
Guest favorite
Apartment in Chicago
A Novel Situation at Wrigley
Jan 19 – 26
$109 per night
4.9 out of 5 average rating, 162 reviews
Guest favorite
Apartment in Chicago
Logan Square 2nd Floor Chicago Victorian
Dec 31 – Jan 7
$97 per night
4.96 out of 5 average rating, 252 reviews
Guest favorite
Apartment in Chicago
Roscoe Village One Bed Lux Apartment Near Wrigley
Sep 11 – 18
$98 per night
4.96 out of 5 average rating, 236 reviews
Guest favorite
Apartment in Chicago
Cozy Private Coach House
Apr 10 – 17
$112 per night
4.93 out of 5 average rating, 206 reviews
Guest favorite
Apartment in Chicago
Andersonville Cozy 1 bedroom basement suite
Nov 6 – 13
$109 per night
4.98 out of 5 average rating, 246 reviews
Guest favorite
Apartment in Chicago
Fully Furnished Apartment Wicker Park Free Parking
$105 per night
4.97 out of 5 average rating, 444 reviews
Guest favorite
Apartment in Chicago
Designer Avondale Attic
May 23 – 30
$100 per night
4.97 out of 5 average rating, 115 reviews
Guest favorite
Apartment in Chicago
Turquoise Wonder - Clean, Cozy & Stylish Apt
Aug 1 – 8
$96 per night
4.96 out of 5 average rating, 258 reviews
Guest favorite
Apartment in Evanston
Charming, Sunny Apartment with Backyard Garden
Jan 12 – 19
$112 per night
4.96 out of 5 average rating, 394 reviews
Guest favorite
Apartment in Skokie
Cozy Garden Unit in Quiet Neighborhood
Sep 30 – Oct 7
$110 per night
4.91 out of 5 average rating, 523 reviews
Guest favorite
Apartment in Chicago
Logan Square Studio
Dec 26 – Jan 2
$88 per night
4.87 out of 5 average rating, 481 reviews

Quick stats about vacation rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K 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 1,180 condo rentals, over 1,850 house rentals to over 6,030 apartment 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 6,650 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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