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

Hotel room in Chicago
4.54 out of 5 average rating, 139 reviewsOnsite spa and indoor/outdoor rooftop bar

Private room in Chicago
4.68 out of 5 average rating, 355 reviewsB1 - Next to Downtown Chicago - Private Room
Superhost

Private room in Chicago
5 out of 5 average rating, 3 reviewsA8- 6 min Walk to Pink Line
Guest favourite

Private room in Chicago
4.76 out of 5 average rating, 530 reviews"Wine" Room - 1 block from train, Victorian Charm
Guest favourite

Private room in Chicago
4.93 out of 5 average rating, 15 reviewsChicagoChinatownCenterB
Top guest favourite

Private room in Chicago
4.95 out of 5 average rating, 41 reviewsStylish Condo BR w/Skyline Views – Walk Score 95

Hotel room in Chicago
4.81 out of 5 average rating, 26 reviewsAdventure Awaits! Close to 360 Chicago! Parking!
Guest favourite

Private room in Chicago
4.89 out of 5 average rating, 18 reviewsQuiet and relaxing kind bed
Destinations to explore
- Chicago Holiday rentals
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- Rentals with beach access Downtown Chicago
- House rentals Downtown Chicago
- Rentals with pools Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with a sauna Downtown Chicago
- Townhouse rentals Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Rentals with lake access Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Waterfront rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Smoking-friendly rentals Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Illinois Beach State Park
- Wicker Park
- Lincoln Park Zoo
- Museum of Science and Industry
- Washington Park Zoo
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Downtown Chicago
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- Tours Downtown Chicago
- Sports activities Downtown Chicago
- Food and drink Downtown Chicago
- Art and culture Downtown Chicago
- Nature and outdoors Downtown Chicago
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