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Vacation rental apartments in Chicago

Book downtown vacation rental apartments, houses, and more on Airbnb

Top-rated apartments in Chicago

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

Rental unit in Chicago
Sonder South Wabash | Superior One-Bedroom Apartment w/ Balcony
Welcome to South Wabash — your modern South Loop sanctuary. Where each sophisticated space includes a fully equipped kitchen, in-suite laundry, and stunning Chicago views. Colorful art pieces complement the industrial exposed concrete ceilings. And floor-to-ceiling windows burst with natural night. There’s always something to do in the Windy City. Field Museum hosts fascinating exhibitions, Grant Park is perfect for a stroll, and South Michigan Avenue has the best restaurants. Victory Tap is around the corner and “Mama’s Meatballs” will leave your tasetbuds watering. Whether you like jazz, opera, or dive bar karaoke, the South Loop has entertainment for everyone. At South Wabash, the best of the city is on your doorstep.
Private room in West Town
Stylish & Ample 1PBR TWO Miles From Downtown
The apartment is wonderfully spacious, bright, and airy with soaring seven-foot windows that have an amazing view of downtown. The place is kept clean, tidy, and organized. All the amenities for a comfortable stay are provided (see list). This “Shared Listing” is a value option where you save costs by sharing common area space with other guests staying in separate lockable bedrooms. Also, the building is conveniently located near the train station giving easy access to other areas of Chicagoland
Individual Host
SUPERHOST
Rental unit in Logan Square
Hip Chicago Apartment - FREE Parking Spot Included
You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run
Individual Host

Vacation rentals for every style

Get the amount of space that is right for you

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Stay near Chicago's top sights

Photo of Museum of Science and Industry
Museum of Science and Industry483 locals recommend
Photo of Cloud Gate
Cloud Gate473 locals recommend
Photo of Millennium Park
Millennium Park1,244 locals recommend
Photo of Navy Pier
Navy Pier927 locals recommend
Photo of Buckingham Fountain
Buckingham Fountain219 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago1,159 locals recommend

Houses in Chicago

Home in Pilsen Historic District
Exclusive and Spacious Pilsen Guest House
Professional Host
SUPERHOST
Private room in Little Italy
Private Room in Great Location to City
Individual Host
Private room in Chicago
Little Farm in the City Back Bedroom
Professional Host
SUPERHOST
Private room in Woodlawn
Luxury BR w/private bath 4mins to Univ & Hospital
Individual Host
Private room in Near West Side
Room T6
Individual Host
Private room in East Rogers Park
#1 Historic Chicago Home - Private Queen Bedroom
Individual Host
SUPERHOST
Private room in Near West Side
Room T5
Individual Host
Private room in McKinley Park
Self Check in 9 min Downtown Chicago Queen Bed
Private room in Bridgeport
Luxury Stay near Downtown Chicago New Queen Bed
Professional Host
Private room in Oak Park
warm comfortable home with lots to offer
Individual Host
SUPERHOST
Private room in Evanston
A place for scholars & solo adventurers w/parking
Individual Host
SUPERHOST
Private room in Woodlawn
Modern Oasis 4min to University & Hospital
Individual Host

Pet-friendly apartments

Rental unit in West Town
New Spot in West Town pt.2!
Individual Host
Rental unit in West Town
Great location. Free parking.
Individual Host
SUPERHOST
Rental unit in West Loop
1BR Perfect Home in the City, Close to Everything
Professional Host
Rental unit in Streeterville
Guest Room with 1 King Bed at Aloft Chicago Mag Mile
Individual Host
SUPERHOST
Rental unit in West Loop
1BR West Loop Apt, In-Unit Laundry, Public Parking
Professional Host
Rental unit in Uptown
Elegant Uptown Studio near Red Line Pets welocme!
Professional Host
SUPERHOST
Rental unit in Near North Side
10% Winter Promo! Goose Island Well-Decorated 1BR
Rental unit in West Town
New Spot in West Town
Individual Host
Rental unit in West Loop
Adorable 1BR Apt in Famed West Loop
Rental unit in The Loop
Sentral Studio Apt in South Loop Chicago
Professional Host
Rental unit in Lincoln Park
Lincoln Park / Old Town, Roomy Nook
SUPERHOST
Rental unit in Logan Square
Massive Deck, Sauna & Dog Friendly - NEWLY UPDATED
Individual Host
SUPERHOST

Apartments with WiFi

Rental unit in Pilsen Historic District
Pilsen 2F *In-Unit Laundry* 2bed/1bath !Location!
Individual Host
SUPERHOST
Rental unit in Edgewater
Loyola University | Cosy Apartment
Individual Host
Rental unit in Bridgeport
!3R Location! 2bed/2bath StepstoSouthLoop +Laundry
Individual Host
SUPERHOST
Rental unit in East Rogers Park
Short-Term Sublet Near Lake Michigan
Individual Host
SUPERHOST
Rental unit in Bridgeport
Bridgeport_cp 3R 2bed/1bath + Free Laundry
Individual Host
SUPERHOST
Rental unit in Bridgeport
!1F Location! 2bed/1bath StepstoSouthLoop +Laundry
Individual Host
SUPERHOST
Rental unit in Chicago
Pilsen HofC Boutique *In-Unit Laundry* 2bed/1bath
Individual Host
SUPERHOST
Rental unit in Irving Park
Modern Chicago Loft with a Complimentary Garage Spot
Individual Host
PLUS
Rental unit in Logan Square
Clean & Bright Chicago Condo - FREE Parking Spot
Individual Host
Private room in West Town
Stylish & Bright 1PBR 2 Miles From Downtown
Individual Host
SUPERHOST
Rental unit in Pilsen Historic District
Pilsen 3R 1bed/1bath + Free Laundry +GreatLocation
Individual Host
SUPERHOST
Rental unit in Lake View
10% Winter Promo! Comfy 1BR Spacious Chicago Apt

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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