
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
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Popular amenities for Downtown Chicago holiday rentals
Other great holiday rentals in Downtown Chicago

Private room in Chicago
4.73 out of 5 average rating, 41 reviewsBees Knees - Room 3
Superhost

Flat in Chicago
4.77 out of 5 average rating, 43 reviewsLoop City Views: 2BR Apt, Near Riverwalk

Hotel room in Chicago
4.83 out of 5 average rating, 6 reviewsCity Escape! Pets Allowed, Parking!

Hotel room in Chicago
4.72 out of 5 average rating, 39 reviewsIndoor pool & 24/7 snacks

Hotel room in Chicago
5 out of 5 average rating, 3 reviewsNewly reno’d king room with sweet city views
Guest favourite

Private room in Chicago
5 out of 5 average rating, 15 reviewsThe Champlain Suite
Guest favourite

Private room in Chicago
5 out of 5 average rating, 8 reviewsChicagoland Guest Room

Hotel room in Chicago
4.55 out of 5 average rating, 495 reviewsPlayful spirit and sustainable practices
Destinations to explore
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- Apartment rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Loft rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Townhouse rentals Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with pools Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- House rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Hotel rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Rentals with beach access Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Rentals with a patio Downtown Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Humboldt Park
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
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