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
Apartment in Uptown
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Apartment in Portage Park
4.96 out of 5 average rating, 114 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Irving Park
4.86 out of 5 average rating, 106 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apartment in Chicago
4.96 out of 5 average rating, 382 reviewsKing Bed, Huge Spa Shower, Dining Destination
Apartment in Wicker Park
4.95 out of 5 average rating, 259 reviewsHeart of Bucktown
Apartment in Logan Square
4.89 out of 5 average rating, 347 reviewsSunny Logan Square Artists' home
Apartment in Chicago
4.99 out of 5 average rating, 198 reviewsExplore Lincoln Park from a Polished Apartment
Apartment in Chicago
4.82 out of 5 average rating, 442 reviewsLovely Andersonville Apt with Ideal Location
Private apartment rentals
Apartment in Pilsen Historic District
4.87 out of 5 average rating, 339 reviewsCozy Garden Apartment in Heart of Pilsen
Apartment in Logan Square
4.87 out of 5 average rating, 488 reviewsLogan Square Studio
Apartment in Lincoln Square
4.94 out of 5 average rating, 193 reviewsSpacious, light-drenched studio-private entrance!
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 240 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Wicker Park
4.78 out of 5 average rating, 222 reviewsPrivate Studio Apt in the Heart of Wicker Park!
Apartment in Wicker Park
4.83 out of 5 average rating, 483 reviewsRelaxed Bucktown/Wicker Park 1B Apt
Apartment in Chicago
4.78 out of 5 average rating, 130 reviewsChic & Fully Furnished Studio Apt with Laundry
Apartment in Wicker Park
4.97 out of 5 average rating, 237 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
4.88 out of 5 average rating, 399 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Apartment in West Loop
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Chicago
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Apartment in Streeterville
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Apartment in West Loop
5.0 out of 5 average rating, 11 reviewsSkyline Oasis: City & Lake Views
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
- Serviced apartment rentals United States
- Apartment rentals United States
- Apartment rentals Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a home theatre Downtown Chicago
- Rentals with a fire pit Downtown Chicago
- Loft rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Condo rentals Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with pools Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
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- Monthly Rentals Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Kid-friendly rentals Downtown Chicago
- Apartment rentals Milwaukee
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- Apartment rentals Illinois
- Apartment rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
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- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
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