Holiday rentals in Downtown Chicago
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Top-rated holiday rentals in Downtown Chicago
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago
Guest favourite
Guest suite in Lincoln Square
4.91 out of 5 average rating, 420 reviewsCozy, Quiet, Garden Getaway!
23–30 Mar
€ 112 per night
Guest favourite
Loft in Lake View
4.96 out of 5 average rating, 418 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
11–18 Nov
€ 183 per night
Guest favourite
Flat in Humboldt Park
4.98 out of 5 average rating, 107 reviewsHumboldt Park Loft
15–22 Oct
€ 154 per night
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 172 reviewsBike the Lakefront from a Sleek Urban Retreat
11–18 Feb
€ 145 per night
Guest favourite
Flat in Logan Square
4.9 out of 5 average rating, 257 reviewsBright & Lofty Bucktown 1br
8–15 Jan
€ 163 per night
Superhost
Flat in Chicago
4.81 out of 5 average rating, 86 reviewsMcCormick Pl 420 friendly 1br/1ba parking/sleeps 4
21–28 Jan
€ 103 per night
Superhost
Flat in Chicago
4.79 out of 5 average rating, 67 reviewsMcCormick Place Studio/parking/sleeps up to 4
17–24 Jan
€ 103 per night
Guest favourite
Flat in Portage Park
4.96 out of 5 average rating, 52 reviewsComfy & Private Chicago Studio
3–10 Apr
€ 110 per night
Destinations to explore
- Milwaukee Holiday rentals
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- Chicago Holiday rentals
- Rentals with pools Downtown Chicago
- Rentals with a patio Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Loft rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
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- Boutique hotel rentals Downtown Chicago
- Monthly Rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Beachfront rentals Downtown Chicago
- House rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
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