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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 · The Loop
Cozy Studio With Beautiful Lake View
Enjoy a stylish experience at this centrally-located place. Studio close to Adler Planetarium, Field Museum, Shedd Aquarium, and Soldier Field. Navy Pier just minutes away. Enjoy a nice walk down Michigan Ave to Grant State Park. Studio fully equipped with: WiFi Tv Netflix, Hulu Travel size shower amenities Toothbrush Feminine hygiene products Hair Dryer Hair Straightener Clothes steamer Keurig Sofa bed Parking available in public paid parking garage across the street
Private room · Pilsen Historic District
In the heart of Pilsen, Self Check In
Host has been fully vaccinated. I clean all rooms to CDC guidelines. TV just added in bedroom, with Roku streaming stick. Close to UIC and medical district. My place is very close to downtown and the Lakefront. Uber and Lyft cab service arrives within 5 minutes, Divvy bikes 1 block away. My neighborhood is the new hot spot. Great food, bars, and art galleries. You’ll love my place because of the coziness, the kitchen And nice people.

Holiday rentals for every style

Get the amount of space that is right for you.

  • Guest suites
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Stay near Chicago's top sights

Photo of Millennium Park
Millennium Park475 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 Chicago440 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
Private room · Oak Park
warm comfortable home with lots to offer
Private room · McKinley Park
Downtown Chicago 8 minutes away SELF CHECK IN
Private room · Chicago
Little Farm in the City Back Bedroom
Private room · Des Plaines
R1 Delightful room overlooking the wild forest
Private room · Little Italy
Great Location Private Room-5 min to the City
Entire home · North Park
Rare Find! See the leaves change color this Oct!
Private room · McKinley Park
Downtown Chicago 8 minutes away New Queen Bed
Private room · East Rogers Park
#4 Historic Chicago Home - Private Single Bedroom
Private room · Pilsen Historic District
Sunny full floor (4+) & gym!
Private room · Pilsen Historic District
Spacious & serene in hip spot. Sleeps 4.
Entire home · West Town
Paradise on the Park

Pet-friendly apartments

Entire rental unit · West Town
Great location. Free parking.
Entire rental unit · West Town
New Spot in West Town
Entire rental unit · Pilsen Historic District
Walk to it all in Pilsen
Entire rental unit · West Loop
1BR Perfect Home in the City, Close to Everything
Entire rental unit · Park Ridge
Modern Garden apartment (WHOLE UNIT)
Entire rental unit · Berwyn
Lovely 1-bedroom condominium with free designated parking on premises
Entire rental unit · Ukrainian Village
Ukrainian Village Garden Retreat
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 · Logan Square
Comfy and Clean 3 bedroom in Logan Square
Entire rental unit · Lincoln Park
Rare, Updated 1 BR Condo in Lincoln Park!
Entire rental unit · Irving Park
⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️

Apartments with kitchens

Entire rental unit · West Town
Cabin #207 at 747 Lofts
Private room · West Town
Stylish & Bright 1PBR TWO Miles From Downtown
Private room · Near South Side
Spectacular Downtown High Rise Extraordinary view
Private room · Chicago
City View near Downtown Chicago Sox & Chinatown
Private room · Englewood
Living in a dream (unit 2 room #5)
Entire rental unit · Old Town
Cozy Gold Coast Studio #413
Entire rental unit · Oak Park
Sunny Jumbo Studio in the Heart of Oak Park
Private room · Wicker Park
Spacious & Bright Private Room in Wicker Park
Entire rental unit · Uptown
Stylish studio at Uptown by Red Line
Private room · Humboldt Park
Fashionable Room w/ full bathroom - FREE PARKING!
Private room · Humboldt Park
Spacious PRVT Room w/ Full Bathroom - Logan Square
Private room · Logan Square
P3. Next to Downtown! Best location
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