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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 Irving Park
Modern Chicago Loft with a Complimentary Garage Spot
Dine by the natural wood breakfast bar or on the rooftop deck. This classy loft boasts open-plan living, exposed brickwork and stunning artwork. Check out our other available listings within the same building by clicking below on our host profile. Welcome to a brand new industrial chic retreat. This unit was designed and remodeled to perfection features exposed brick entertaining area with a smart TV and complimentary Netflix, fully equipped kitchen with stainless steel appliances and a natural wood bar perfect for a couple. Also you will find an extremely comfortable Queen size bed with memory foam mattress and clean sheets. The brand new bathroom has everything you will need for your stay including clean towels, toiletry and a hair dryer. One garaged parking spot provided free of charge. Entire unit and deck, one garage spot provided free of charge. In the heart of Avondale, near six corners with many shops and restaurants. Wicker Park is also nearby, where there are a lot of restaurants, cafes, clubs and bars. Uber and/or Lyft are the best options for getting around the Chicago area, with very reasonable pricing, especially if you use Uber Pool. If you are a public transportation person there is the Milwaukee CTA bus outside of the building and the Blue line is less than a mile away from the unit. If you have a vehicle the 90/94 HWY is very close by and can get you anywhere in the city.
$60 per night
PLUS
Condo in Little Italy
Private hot tub and king bed suite
Welcome to this historic yet chic retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best entertainment, museums, shopping, food and nightlife the city has to offer. At the end of your day, enjoy a relaxing soak in your private outdoor patio hot tub before sinking in to your Tempur-Pedic king bed for a restful night's sleep.
$122 per night
SUPERHOST
Condo in Logan Square
Bucktown high-end condo w/outdoor patio /APT 1
This freshly remodeled condo decorated in the Japandi style is set in the trendy yet peaceful neighborhood of Bucktown - a perfect base for exploring Chicago. A short walking distance to 2 Blue line CTA stops (Western and Damen), it is surrounded by quaint neighborhood bars, restaurants, and coffee shops as well as grocery stores and trendy shopping.
$104 per night
SUPERHOST

Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park1,244 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 United Center
United Center199 locals recommend
Photo of Grant Park
Grant Park332 locals recommend

Downtown Chicago vacation rentals

Rental unit in Irving Park
Cozy and Stylish Studio with Free Parking in Irving Park
$52 per night
PLUS
Rental unit in Lake View
Uplifting Studio Apartment in Belmont
$52 per night
Private room in Lake View
Queen Bed with Private Bathroom in Boystown
$48 per night
SUPERHOST
Hotel room in Near North Side
Hotel Perks - Private Bedroom | Private Bathroom
$97 per night
Private room in West Town
Stylish & Ample 1PBR TWO Miles From Downtown
$46 per night
SUPERHOST
Rental unit in Uptown
Vibrant studio close to Andersonville and train
$47 per night
SUPERHOST
Rental unit in Logan Square
Lofted 2nd Floor Apartment with Spiral Staircase
$70 per night
Rental unit in Lake View
Beautiful Belmont 1BR Apt w/ In-Unit Washer/Dryer
$67 per night
Rental unit in Lake View
Lux 1BR/1BA Apartment in Belmont
$62 per night
Rental unit in Lake View
Best Studio Apt Near Boystown!
$47 per night
Rental unit in Near North Side
52nd Floor MagMile Penthouse Views Fireplace Pool
$159 per night
SUPERHOST
Private room in McKinley Park
Downtown Chicago 8 minutes away New Queen Bed
$29 per night

Chicago summer vacation rentals

Rental unit in Lake View
Splendid 1BR Apt in Lakeview
$46 per night
Rental unit in Wicker Park
1-Bedroom Unit with Free Garage Parking
$86 per night
Rental unit in Irving Park
Explore Chicago from an Urban Sanctuary with Free Parking
$60 per night
PLUS
Private room in West Town
Stylish & Bright 1PBR 2 Miles From Downtown
$46 per night
SUPERHOST
Rental unit in Uptown
Modern studio at Uptown by Red Line,Aragon,Riviera
$49 per night
SUPERHOST
Rental unit in Lake View
10% Winter Promo! Delightful 1BR Apt in Belmont
$59 per night
Rental unit in Lake View
10% Winter Promo! Comfy Studio Close to Boystown
$45 per night
Rental unit in Lake View
10% Winter Promo! Lakeview 1BR Apt Near Shops
$41 per night
Rental unit in Lake View
Adorable Studio Apartment in Lakeview
$47 per night
Private room in Englewood
Work from home beauty (unit 2 room #4)
$24 per night
SUPERHOST
Private room in Chicago
New Queen bed near Downtown Chicago Chinatown
$29 per night
Private room in Bridgeport
5 min to Chinatown 10min to Downtown Chicago
$28 per night

Chicago holiday vacation rentals

Private room in Bridgeport
The Modern Bedroom in Bridgeport Chicago
$30 per night
Private room in Chicago
City View near Downtown Chicago Sox & Chinatown
$30 per night
Rental unit in Lake View
1BR Attractive Rental Unit in Chicago
$46 per night
Rental unit in Lake View
Remodeled Studio Apt in East Lakeview
$46 per night
Private room in West Town
Stylish & Ample 1PBR 2 Miles From Downtown
$38 per night
SUPERHOST
Private room in Lake View
Bright Room with a Garden View
$41 per night
SUPERHOST
Private room in Englewood
Living in a dream (unit 2 room #5)
$23 per night
SUPERHOST
Private room in Bridgeport
The Couple Room in Bridgeport Chicago
$28 per night
Rental unit in Uptown
Vibrant studio at Uptown by Red Line (02)
$49 per night
SUPERHOST
Rental unit in Lake View
Stylish & Fully Furnished Studio Apt in Lakeview
$47 per night
Guesthouse in Wicker Park
Unwind in the Bath at a Hip, Historic Coach House
$95 per night
PLUS
Rental unit in Irving Park
Private Entrance|Free Parking Space|2BR|Lincoln Sq
$78 per night
SUPERHOST

Stays in Downtown Chicago

Rental unit in The Loop
Theater District Hideaway
$126 per night
Rental unit in Chicago
McCormick Place Studio/parking/sleeps up to 4
$100 per night
SUPERHOST
Condo in Chicago
McCormick Place Studio/parking/sleeps up to 4
$102 per night
SUPERHOST
Rental unit in Chicago
McCormick 420 friendly 2br/2ba
$128 per night
SUPERHOST

Stays in Lincoln Park

Rental unit in Lincoln Park
Rare, Updated 1 BR Condo in Lincoln Park!
$100 per night
Rental unit in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
$121 per night
SUPERHOST
Condo in Lincoln Park
Exclusive Condo Steps from Old Town + Lincoln Park
$102 per night
SUPERHOST
Condo in Lincoln Park
Centrally Located Old Town Gem
$103 per night
SUPERHOST

Stays in Wrigleyville

Condo in Wrigleyville
Sunny Apartment Just 2 Blocks from Wrigley and Boystown
$120 per night
PLUS
Rental unit in Wrigleyville
Peculiar but posh ground floor flat
$76 per night
SUPERHOST
Rental unit in Lake View
Stylish|Cozy Getaway in Lakeview|1BR|3min~Wrigley
$62 per night
SUPERHOST
Private room in Lake View
Cute room in downtown Boystown
$42 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.

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