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
Get the amount of space that is right for you
Popular amenities for Chicago Loop apartment rentals
Weekly apartment rentals
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 5 – 12
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 243 reviewsModern
Oct 24 – 31
Apartment in Roscoe Village
4.96 out of 5 average rating, 238 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Nov 19 – 26
Apartment in Chicago
4.98 out of 5 average rating, 131 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 26 – Aug 2
Apartment in Lincoln Square
4.96 out of 5 average rating, 323 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
Dec 18 – 25
Apartment in Uptown
4.96 out of 5 average rating, 266 reviewsCozy loft in Chicago's Uptown
Oct 16 – 23
Apartment in Pilsen Historic District
4.85 out of 5 average rating, 234 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Oct 2 – 9
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Oct 1 – 8
Private apartment rentals
Apartment in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
Oct 15 – 22
Apartment in West Town
4.9 out of 5 average rating, 125 reviewsSpacious & New Modern-Chic Condo Close to Downtown
Feb 9 – 16
Apartment in Chicago
4.99 out of 5 average rating, 104 reviewsNewly Renovated, Spacious 2BR in Andersonville
Dec 7 – 14
Apartment in East Rogers Park
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Mar 18 – 25
Apartment in Irving Park
4.86 out of 5 average rating, 102 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
Apr 4 – 11
Apartment in Pilsen Historic District
4.82 out of 5 average rating, 431 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
Oct 21 – 28
Apartment in Lincoln Square
4.81 out of 5 average rating, 124 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 8 – 15
Apartment in Lake View
4.99 out of 5 average rating, 230 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
Jan 31 – Feb 7
Apartment rentals with a hot tub
Apartment in Near South Side
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 15 – 22
Apartment in West Town
4.88 out of 5 average rating, 394 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 24 – 31
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Oct 3 – 10
Apartment in The Loop
5.0 out of 5 average rating, 6 reviewsThe Downtown Oasis (2BD / 2BA)
Feb 10 – 17
Apartment in Logan Square
4.91 out of 5 average rating, 32 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Nov 25 – Dec 2
Apartment in West Loop
5.0 out of 5 average rating, 10 reviewsSkyline Oasis: City & Lake Views
Sep 20 – 27
Apartment in West Town
4.88 out of 5 average rating, 42 reviewsCloud 9 | Presidential Penthouse Suite | The Iris
Feb 24 – Mar 3
Apartment in West Rogers Park
4.95 out of 5 average rating, 19 reviewsSpacious Beautiful Condo
Oct 23 – 30
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
$10 before taxes and fees
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