Apartment holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop apartment rentals
Weekly apartment rentals
Flat in Chicago
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
15–22 Feb
Flat in Chicago
4.87 out of 5 average rating, 331 reviewsCozy Garden Apartment in Heart of Pilsen
11–18 Mar
Flat in Chicago
4.97 out of 5 average rating, 455 reviewsFully Furnished Apartment Wicker Park Free Parking
Flat in Bridgeport
4.98 out of 5 average rating, 170 reviewsBridgeport Garden Apartment
3–10 Oct
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
25 Sep – 2 Oct
Flat in Lake View
4.99 out of 5 average rating, 229 reviewsA Whimsical Fairy-tale Loft in Ravenswood Chicago
24–31 Jan
Flat in Little Italy
4.98 out of 5 average rating, 198 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
24–31 Dec
Flat in Irving Park
4.92 out of 5 average rating, 591 reviewsExplore Chicago from an Urban Sanctuary with Free Parking
25 Jun – 2 Jul
Private apartment rentals
Flat in Chicago
4.99 out of 5 average rating, 194 reviewsExplore Lincoln Park from a Polished Apartment
11–18 Apr
Flat in Logan Square
4.91 out of 5 average rating, 371 reviewsThe Grotto of Logan Square
1–6 Oct
Flat in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
4–11 Oct
Flat in The Loop
4.9 out of 5 average rating, 110 reviewsBright 2BR-2BA steps from The Bean & Michigan Ave
19–26 Dec
Flat in Irving Park
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
4–11 Apr
Flat in Pilsen Historic District
4.82 out of 5 average rating, 429 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
1–8 Oct
Flat in Logan Square
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
2–9 Oct
Flat in Logan Square
4.81 out of 5 average rating, 105 reviewsWelcome Chez Moi
19–26 Aug
Apartment rentals with a hot tub
Flat in West Town
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
9–16 Oct
Flat in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
20–27 Apr
Flat in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
2–9 Oct
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
1–8 Mar
Flat in Logan Square
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
11–18 Mar
Flat in The Loop
5.0 out of 5 average rating, 6 reviewsThe Downtown Oasis (2BD / 2BA)
14–21 Jan
Flat in Streeterville
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
9–16 Jul
Flat in West Rogers Park
5.0 out of 5 average rating, 17 reviewsSpacious Beautiful Condo
14–21 Oct
Quick stats about flat 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
11T reviews
Nightly prices starting at
₹834 before taxes and fees
Destinations to explore
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