Apartment vacation rentals in Chicago Loop
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Top-rated apartment rentals in Chicago Loop
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chicago Loop apartment rentals
Weekly apartment rentals
Apartment in Near West Side
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Apartment in Chicago
4.99 out of 5 average rating, 194 reviewsExplore Lincoln Park from a Polished Apartment
Dec 30 – Jan 6
Apartment in Lake View
4.99 out of 5 average rating, 229 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
Feb 1 – 8
Apartment in The Loop
4.9 out of 5 average rating, 111 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
Apr 2 – 9
Apartment in Chicago
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Dec 2 – 9
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Sep 12 – 19
Apartment in Irving Park
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
Sep 30 – Oct 7
Apartment in East Rogers Park
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Sep 29 – Oct 6
Private apartment rentals
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Jan 4 – 11
Apartment in Logan Square
4.96 out of 5 average rating, 257 reviewsLogan Square 2nd Floor Chicago Victorian
Dec 28 – Jan 4
Apartment in Wicker Park
4.95 out of 5 average rating, 172 reviewsWicker Park/Bucktown Location
Apartment in Irving Park
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 4 – 11
Apartment in Irving Park
4.92 out of 5 average rating, 592 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
Dec 1 – 8
Apartment in Logan Square
4.89 out of 5 average rating, 339 reviewsSunny Logan Square Artists' home
Feb 8 – 15
Apartment in Pilsen Historic District
4.82 out of 5 average rating, 429 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
Sep 29 – Oct 6
Apartment in Near West Side
4.82 out of 5 average rating, 271 reviews*Entire City Apartment 1 block to Train Park Free
Nov 4 – 11
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 29 – Dec 6
Apartment in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Jun 27 – Jul 4
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Sep 12 – 19
Apartment in Logan Square
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 19 – 26
Apartment in The Loop
4.78 out of 5 average rating, 9 reviewsThe Areal Oasis
Sep 21 – 28
Apartment in Streeterville
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 19 – 26
Apartment in The Loop
5.0 out of 5 average rating, 20 reviewsRiver View Cityscape Condo
May 6 – 13
Apartment in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
Aug 18 – 25
Quick stats about apartment rentals in Chicago Loop
Total rentals
540 properties
Rentals with a pool
350 properties have a pool
Pet-friendly rentals
330 properties allow pets
Family-friendly rentals
180 properties are a good fit for families
Total number of reviews
11K reviews
Nightly prices starting at
ﺩ.ﺇ37 before taxes and fees
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