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Chicago vacation rentals

Book unique condos, 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.

Private room in River North
Artist Loft, Private Room
Beautiful shared artist loft space with private room. Located on the top floor of a building built in the early 1900s, enjoy a unique experience in the heart of River North/downtown Chicago. Our One-of-a-kind rooftop garden is a must-see during Summer/early Fall. This space is ideal for socializing. NOTE: Includes 4.5-story walkup, NO ELEVATOR. No exterior window in bedroom, interior window only. ALREADY BOOKED??? If room is unavailable, check out my profile to see our other listings!
$120 per night
Private room in River North
Chicago Speakeasy-Style Loft Space (Room 3A)
Welcome to our Chicago Speakeasy-style loft space. Built in the early 1900s, our two-floor loft provides a unique experience in the heart of River North/downtown Chicago. Centrally located River North Chicago is a go-to district with lively night scene, and a wide variety of restaurants, bars and clubs. There are many public transit stations within walking distance. ALREADY BOOKED??? If this room is unavailable, check out my profile to see our other listings! Feel free to message me!
$114 per night
Private room in Lake View
Bright Room with a Garden View
This room is bright, cozy and offers a view of the garden and off the main street in Boystown, Chicago. The room has a queen bed, tv and small closet. This is a shared bathroom with two other rooms, there is a shared refrigerator on the floor and coffee just outside the room. On the main floor is a shared kitchen, living room and dining room. Wifi all throughout the house. Complimentary continental breakfast is provided in the morning. Parking info below
$80 per night

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
O'Hare International Airport122 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile598 locals recommend

Chicago fishing vacation rentals

Condo in Lake View
Urban Comfort in the Heart of Chicago
$156 per night
Private room in Gold Coast
MAG MILE Private Bed/Bath in a LUX 2BR/2BA Apt
$130 per night
Apartment in Gold Coast
The Magnificent Milestone (2BR)
$196 per night
Apartment in Magnificent Mile
☀️Amazing Gold Coast Apt w/ Rooftop Pool & Gym☀️
$175 per night

Chicago apartment rentals

Apartment in Magnificent Mile
Chic Mag Mile Studio with City View by Zencity
$154 per night
Private room in West Loop
West Loop Loft - Private Loft Room
$100 per night
Apartment in Near North Side
50th Floor Mag Mile Studio
$132 per night
Apartment in Uptown
Stylish studio at Uptown by Red Line
$85 per night

Chicago condo rentals

Condo in West Town
Cabin 207 at 747 Lofts
$59 per night
Condo in West Town
Great location. Free parking.
$100 per night
Condo in Uptown
Vibrant studio at Uptown close to RedLine
$76 per night
Condo in Near South Side
McCormick Place Studio/parking/sleeps up to 4
$224 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.

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