Apartment holiday rentals in Chicago
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Top-rated apartment rentals in Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Flat in Chicago
4.99 out of 5 average rating, 231 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
Flat in Irving Park
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Flat in Chicago
4.93 out of 5 average rating, 208 reviewsCozy Private Coach House
Flat in Chicago
4.93 out of 5 average rating, 382 reviewsRavenswood Guest House Annex
Flat in Oak Park
4.86 out of 5 average rating, 248 reviewsCosmopolitan Nest in Oak Park North Side
Flat in Chicago
4.87 out of 5 average rating, 104 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Flat in Oak Park
4.85 out of 5 average rating, 532 reviewsLong stays welcome@warm&cute vintage 2BR
Flat in Chicago
4.86 out of 5 average rating, 236 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Private apartment rentals
Flat in Chicago
4.95 out of 5 average rating, 110 reviewsComfortable, modern apartment 20 Min from Downtown
Flat in Chicago
4.97 out of 5 average rating, 330 reviewsCharming, Spacious 3BR Lakeview Apt Near Transit
Flat in Andersonville
4.98 out of 5 average rating, 252 reviewsAndersonville Cozy 1 bedroom basement suite
Flat in Des Plaines
4.83 out of 5 average rating, 99 reviewsNewly Renovated, Safe, 1 Bdrm, Self Check-in
Flat in Logan Square
4.91 out of 5 average rating, 373 reviewsThe Grotto of Logan Square
Flat in Chicago
4.89 out of 5 average rating, 209 reviewsNewly Rehabbed! 2br with Vintage Charm
Flat in Chicago
4.86 out of 5 average rating, 202 reviewsPrivate Queen Bedroom and En Suite Bath
Flat in Chicago
4.98 out of 5 average rating, 132 reviewsModern Apt with style & comfort in Pilsen Chicago
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Berwyn
4.91 out of 5 average rating, 204 reviews“Dream slice of urban homesteading.”
Flat in Chicago
4.87 out of 5 average rating, 157 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Chicago
4.91 out of 5 average rating, 33 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
4.81 out of 5 average rating, 26 reviewsThe Professional's Playground
Flat in Chicago
4.86 out of 5 average rating, 21 reviewsSpacious Beautiful Condo
Flat in Magnificent Mile
4.87 out of 5 average rating, 75 reviews4Br Gold Coast Duplex w Jacuzzi in the Bedroom!
Quick stats about flat rentals in Chicago
Total rentals
5.9K properties
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2K properties allow pets
Family-friendly rentals
2.7K properties are a good fit for families
Total number of reviews
253K reviews
Destinations to explore
- Downtown Chicago Holiday rentals
- 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
- Flat rentals United States
- Serviced apartment rentals United States
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an EV charger Chicago
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- Hotel rentals Chicago
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- Flat rentals Downtown Chicago
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- Yurt Rentals United States
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