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
Get the amount of space that is right for you
Popular amenities for Chicago apartment rentals
Weekly apartment rentals
Flat in Chicago
4.98 out of 5 average rating, 128 reviewsModern Apt with style & comfort in Pilsen Chicago
9–16 Jul
Flat in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
13–20 Dec
Flat in West Town
4.98 out of 5 average rating, 218 reviewsUkrainian Village Garden Retreat
20–27 Nov
Flat in Chicago
4.82 out of 5 average rating, 435 reviewsLovely Andersonville Apt with Ideal Location
21–28 Dec
Flat in Chicago
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
17–24 Nov
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsLa Cottage
12–19 Sep
Flat in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
19–26 Apr
Flat in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
27 Feb – 6 Mar
Private apartment rentals
Flat in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
4–11 Jan
Flat in Oak Park
4.86 out of 5 average rating, 247 reviewsCosmopolitan Nest in Oak Park North Side
3–10 Oct
Flat in Chicago
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
6–13 Mar
Flat in Oak Park
4.84 out of 5 average rating, 494 reviewsSunny Jumbo Studio NO cleaning fee!
10–17 Mar
Flat in Oak Park
4.88 out of 5 average rating, 128 reviewsA Little Slice of Heaven in Oak Park, IL
13–20 Feb
Flat in Oak Park
4.92 out of 5 average rating, 196 reviewsClean & Cozy Oak Park Vintage 1BR: Tv NFL PASS
3–10 Jan
Flat in Oak Park
4.97 out of 5 average rating, 163 reviewsChic Retreat in Historic Victorian House-Park Free
28 Jan – 4 Feb
Flat in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
14–21 Oct
Apartment rentals with a hot tub
Flat in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
18–25 Sep
Flat in Berwyn
4.91 out of 5 average rating, 201 reviews“Dream slice of urban homesteading.”
5–12 Mar
Flat in Chicago
4.86 out of 5 average rating, 154 reviewsStunning Panoramic Chicago Views & Free Parking
2–9 Oct
Flat in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
12–19 Jan
Flat in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
5–12 Sep
Flat in Chicago
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
13–20 Jul
Flat in The Loop
4.75 out of 5 average rating, 8 reviewsThe Areal Oasis
9–16 Jun
Flat in Belmont Cragin
5.0 out of 5 average rating, 23 reviewsBelmont Pleasures - hot tub / arcade gaming room
3–10 Mar
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
- Rentals with a hot tub Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Apartment rentals Chicago
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- Family-friendly rentals Chicago
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- Smoking-friendly rentals Chicago
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- Flat rentals Downtown Chicago
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- Flat rentals Cook County
- Yurt Rentals United States
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