Apartment holiday rentals in Downtown Chicago
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Top-rated apartment rentals in Downtown Chicago
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Downtown Chicago apartment rentals
Weekly apartment rentals
Flat in Irving Park
4.86 out of 5 average rating, 101 reviews⭐️⭐️Entire Unite 2-Bdr. HORNER PARK⭐️⭐️
4–11 Apr
Flat in Chicago
4.93 out of 5 average rating, 187 reviewsTaj Ma-small at Wrigley
15–22 Feb
Flat in Chicago
4.96 out of 5 average rating, 237 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
3–10 Nov
Flat in Chicago
4.97 out of 5 average rating, 455 reviewsFully Furnished Apartment Wicker Park Free Parking
Flat in Wicker Park
4.95 out of 5 average rating, 255 reviewsHeart of Bucktown
20–27 Jul
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
Flat in Logan Square
4.91 out of 5 average rating, 372 reviewsThe Grotto of Logan Square
1–6 Oct
Flat in Wicker Park
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
19–26 Feb
Private apartment rentals
Flat in Chicago
4.82 out of 5 average rating, 436 reviewsLovely Andersonville Apt with Ideal Location
18–25 Dec
Flat in Logan Square
4.84 out of 5 average rating, 479 reviewsRelaxed Bucktown/Wicker Park 1B Apt
2–9 Oct
Flat in Chicago
4.85 out of 5 average rating, 162 reviewsYour brand new Chicago suite (unit 1F)
Flat in Near West Side
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Flat in Chicago
4.79 out of 5 average rating, 113 reviewsChic Furnished Studio w/ Laundry
21–28 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 Irving Park
4.97 out of 5 average rating, 251 reviewsSpacious 1BR apartment in a central location
23–30 Sep
Flat in Portage Park
4.95 out of 5 average rating, 106 reviewsComfortable, modern apartment 20 Min from Downtown
24–31 Jan
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 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
Flat in Chicago
5.0 out of 5 average rating, 6 reviewsThe Downtown Oasis (2BD / 2BA)
14–21 Jan
Destinations to explore
- 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
- Chicago Holiday rentals
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Boutique hotel rentals Downtown Chicago
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- Rentals with a washing machine and dryer Downtown Chicago
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- Rentals with an EV charger Downtown Chicago
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- Monthly Rentals Downtown Chicago
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- Flat rentals Milwaukee
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- Yurt Rentals United States
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