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
4.95 out of 5 average rating, 240 reviewsGreat location, private entry and patio!
14–21 Nov
€ 127 per night
Guest favourite
Flat in Lincoln Square
4.95 out of 5 average rating, 22 reviewsLincoln Square Oasis - Bright, clean studio
5–12 Jan
€ 113 per night
Guest favourite
Flat in Chicago
4.97 out of 5 average rating, 30 reviewsSerene Escape with King Sleep Number Bed, No Fees!
2–9 Dec
€ 120 per night
Superhost
Flat in Chicago
4.81 out of 5 average rating, 16 reviewsCozy Condo near Downtown Chicago
10–17 Dec
€ 171 per night
Superhost
Flat in Portage Park
4.96 out of 5 average rating, 50 reviewsComfy & Private Chicago Studio
13–20 Nov
€ 111 per night
Superhost
Flat in Chicago
5.0 out of 5 average rating, 4 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
24–31 Jan
€ 132 per night
Guest favourite
Guest suite in Chicago
4.91 out of 5 average rating, 79 reviewsCozy one-bedroom suite in the heart of West Loop
30 Dec – 6 Jan
€ 165 per night
Guest favourite
Flat in Uptown
5.0 out of 5 average rating, 7 reviewsMajestic Modern Style Loft Montrose Beach WFH Gym
6–13 Feb
€ 132 per night
Destinations to explore
- Milwaukee Holiday rentals
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- Rentals with a patio Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Beachfront rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with lake access Downtown Chicago
- Boutique hotel rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Pet-friendly rentals Downtown Chicago
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- Family-friendly rentals Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Loft rentals Downtown Chicago
- Waterfront rentals Downtown Chicago
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- Monthly Rentals Downtown Chicago
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