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Holiday rental apartments in Chicago

Book unique holiday rentals, apartments, and more on Airbnb

Top-rated apartments in Chicago

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

Entire rental unit · Chicago
Floor to Ceiling Windows 1 Bedroom Corner Unit
Keep it simple at this peaceful and centrally-located place. Just come with your bags and enjoy a beautiful stay with expanding views of the city. Walking distance from multiple fan favorites and close to public transport.
Entire rental unit · Old Town
Cozy Gold Coast Studio #413
This is a perfect apartment and location for a short-term stay. The apartment has a queen size bed and can accommodate 1 or 2 people. The building is located in a residential neighborhood, but is a short walk or commute to downtown Chicago. It's steps to several grocery stores, countless restaurants and shops. Walk to Michigan Avenue or the lakefront.
Entire rental unit · West Loop
1BR West Loop Apt, In-Unit Laundry, Public Parking
Welcome to Chicago West Loop-Fulton! Our 1BR apartment is a perfect place to stay on any Chicago getaway, whether business or vacation. It is professionally designed with everything you need to live. There's public parking 2 blocks away on the corner of N Clinton St. and W Lake St. Along this stretch, you'll find varieties of shops, restaurants, and convenience stores. The building is across from the train station. Clinton Subway is 3 mins walk. Going downtown only takes approximately 15 mins.

Holiday 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 Millennium Park
Millennium Park474 locals recommend
Photo of Navy Pier
Navy Pier307 locals recommend
Photo of Willis Tower
Willis Tower154 locals recommend
Photo of Cloud Gate
Cloud Gate166 locals recommend
Photo of The Art Institute of Chicago
The Art Institute of Chicago439 locals recommend
Photo of Museum of Science and Industry, Chicago
Museum of Science and Industry, Chicago191 locals recommend

Houses in Chicago

Private room · Near West Side
Room T6
Entire home · North Park
Rare Find! See the leaves change color this Oct!
Private room · South Chicago
Room H6
Private room · Near West Side
Room T2
Private room · McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
Private room · McKinley Park
Cleanest & Newest place near Downtown Chicago
Private room · Austin
Little Farm in the City Back Bedroom
Private room · Oak Park
warm comfortable home with lots to offer
Private room · Chinatown
Hotel quality room near Downtown,CTA, McCormick
Private room · Des Plaines
R1 Delightful room overlooking the wild forest
Private room · Little Italy
Great Location Private Room-5 min to the City
Private room · East Rogers Park
#4 Historic Chicago Home - Private Single Bedroom

Pet-friendly apartments

Entire rental unit · West Town
Great location. Free parking.
Entire rental unit · Lincoln Park
Rare, Updated 1 BR Condo in Lincoln Park!
Entire rental unit · Lincoln Square
Charming Bowmanville 1BR Apt w/ Roomy Living Room
Entire rental unit · West Loop
Adorable 1BR Apt in Famed West Loop
Entire rental unit · Logan Square
Modern 2BR Apt with Cozy Interior at Logan Square
Entire rental unit · Park Ridge
Modern Garden apartment (WHOLE UNIT)
Entire rental unit · Woodlawn
Luxury 3 bedroom unit in Historical Neighborhood.
Entire rental unit · Berwyn
Lovely 1-bedroom condominium with free designated parking on premises
Private room · Ukrainian Village
Charming 1-bedroom in shared 420-F penthouse loft.
Entire rental unit · Chicago
Newly Renovated 420 Friendly unit
Entire rental unit · Ukrainian Village
Ukrainian Village Garden Retreat
Entire rental unit · Uptown
Uptown Minimalist Design Studio Apt near Dining

Apartments with kitchens

Private room · Pilsen Historic District
In the heart of Pilsen, Self Check In
Private room · Logan Square
P8. Next to Downtown! Best location! Small bedroom
Private room · West Town
Stylish & Bright 1PBR TWO Miles From Downtown
Private room · Englewood
Living in a dream (unit 2 room #5)
Entire rental unit · West Town
Cabin #207 at 747 Lofts
Private room · Chicago
City View near Downtown Chicago Sox & Chinatown
Entire rental unit · Uptown
Stylish studio at Uptown by Red Line
Private room · Near South Side
Stunning downtown High Rise apartment amazing view
Private room · West Town
Stylish & Ample 1PBR TWO Miles From Downtown
Private room · Chicago
Private Bedroom near Downtown Chicago Chinatown
Entire rental unit · West Town
Cabin #103 at 747 Lofts
Private room · Wicker Park
Spacious & Bright Private Room in Wicker Park
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