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 Forest Park
4.93 out of 5 average rating, 584 reviewsPeaceful oasis in Forest Park
24–31 Aug
Flat in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
10–17 Dec
Flat in Chicago
4.92 out of 5 average rating, 186 reviewsTaj Ma-small at Wrigley
1–8 Mar
Flat in Oak Park
4.85 out of 5 average rating, 527 reviewsLong stays welcome@warm&cute vintage 2BR
15–22 Oct
Flat in Logan Square
4.93 out of 5 average rating, 207 reviewsCozy Private Coach House
25 Jul – 1 Aug
Flat in Irving Park
4.89 out of 5 average rating, 176 reviewsHistoric Chicago neighborhood flat
10–17 Nov
Flat in Logan Square
4.87 out of 5 average rating, 484 reviewsLogan Square Studio
2–9 Jan
Flat in Lake View
4.86 out of 5 average rating, 201 reviewsPrivate Queen Bedroom and En Suite Bath
3–10 Jul
Private apartment rentals
Flat in Chicago
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
13–20 Apr
Flat in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
3–10 Oct
Flat in Andersonville
4.98 out of 5 average rating, 249 reviewsAndersonville Cozy 1 bedroom basement suite
26 Nov – 3 Dec
Flat in Logan Square
4.9 out of 5 average rating, 283 reviewsModern Logan Square Apartment, steps from train!
1–8 Jan
Flat in Chicago
4.84 out of 5 average rating, 130 reviewsPerfect Private Getaway in Perfect Pilsen
6–13 Aug
Flat in Wicker Park
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
14–21 Oct
Flat in Chicago
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
5–12 Mar
Flat in Chicago
4.79 out of 5 average rating, 172 reviewsPerfect 1br In Lincoln Park - Steps to Depaul!
4–11 Jan
Apartment rentals with a hot tub
Flat in Berwyn
4.91 out of 5 average rating, 202 reviews“Dream slice of urban homesteading.”
9–16 Feb
Flat in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
16–23 Jul
Flat in Chicago
4.86 out of 5 average rating, 155 reviewsStunning Panoramic Chicago Views & Free Parking
2–9 Nov
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
15–22 May
Flat in Chicago
4.93 out of 5 average rating, 28 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
10–17 Mar
Flat in Chicago
5.0 out of 5 average rating, 16 reviewsSpacious Beautiful Condo
10–17 Sep
Flat in Streeterville
5.0 out of 5 average rating, 9 reviewsLake, City, & River View Condo
6–13 May
Flat in Chicago
4.79 out of 5 average rating, 24 reviewsThe Professional's Playground
2–9 Jan
Quick stats about flat rentals in Chicago
Total rentals
5.9T properties
Rentals with dedicated workspaces
3.8T properties have a dedicated workspace
Rentals with a pool
750 properties have a pool
Pet-friendly rentals
2T properties allow pets
Family-friendly rentals
2.7T properties are a good fit for families
Total number of reviews
2.5L 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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- Monthly Rentals Chicago
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- Rentals with a washing machine and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with a firepit Chicago
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- Waterfront rentals Chicago
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- Mansion rentals Chicago
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- Villa rentals Chicago
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- Smoking-friendly rentals Chicago
- Rentals with a balcony Chicago
- Flat rentals Downtown Chicago
- Flat rentals Milwaukee
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- Flat rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
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- Condo Rentals United States
- Holiday Apartments Australia
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