Apartment holiday rentals in Downtown Chicago
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Top-rated apartment rentals in Downtown Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals
Flat in Irving Park
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Flat in Pilsen Historic District
4.89 out of 5 average rating, 247 reviewsModern
Flat in Chicago
4.95 out of 5 average rating, 243 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Flat in Chicago
4.96 out of 5 average rating, 380 reviewsKing Bed, Huge Spa Shower, Dining Destination
Flat in Chicago
4.84 out of 5 average rating, 132 reviewsPerfect Private Getaway in Perfect Pilsen
Flat in Logan Square
4.9 out of 5 average rating, 345 reviewsSunny Logan Square Artists' home
Flat in Lake View
4.93 out of 5 average rating, 171 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
Private apartment rentals
Flat in Wicker Park
4.95 out of 5 average rating, 175 reviewsWicker Park/Bucktown Location
Flat in Pilsen Historic District
4.85 out of 5 average rating, 237 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Flat in Portage Park
4.96 out of 5 average rating, 113 reviewsComfortable, modern apartment 20 Min from Downtown
Flat in Near West Side
4.82 out of 5 average rating, 277 reviews*Entire City Apartment 1 block to Train Park Free
Flat in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Flat in Wicker Park
4.83 out of 5 average rating, 482 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Flat in Logan Square
4.8 out of 5 average rating, 111 reviewsWelcome Chez Moi
Flat in Lake View
4.85 out of 5 average rating, 445 reviewsSleek and cool garden loft in East Lakeview
Apartment rentals with a hot tub
Flat in Near South Side
4.87 out of 5 average rating, 159 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Town
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Berwyn
4.91 out of 5 average rating, 206 reviews“Dream slice of urban homesteading.”
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Logan Square
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Flat in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Flat in West Rogers Park
4.78 out of 5 average rating, 23 reviewsSpacious Beautiful Condo
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Flat rentals United States
- Serviced apartment rentals United States
- Flat rentals Chicago
- Loft rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a firepit Downtown Chicago
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- Pet-friendly rentals Downtown Chicago
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- Apartment rentals Downtown Chicago
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- House rentals Downtown Chicago
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- Flat rentals Milwaukee
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- Yurt Rentals United States
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