
Holiday rentals in Downtown Chicago
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Top-rated holiday rentals in Downtown Chicago
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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
Guest favourite

Private room in Chicago
4.95 out of 5 average rating, 42 reviewsPrivate Room in Rogers Park

Private room in Chicago
4.73 out of 5 average rating, 40 reviewsBees Knees - Room 3

Private room in Chicago
4.86 out of 5 average rating, 7 reviewsChicagoChinatownCenterB

Private room in Chicago
4.84 out of 5 average rating, 49 reviewsYellow Room - South Shore Bungalow
Superhost

Private room in Chicago
4.78 out of 5 average rating, 188 reviewsCozy, Quiet, Private bathroom in private room

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

Private room in Chicago
4.94 out of 5 average rating, 34 reviewsStylish Condo BR w/Skyline Views – Walk Score 95

Private room in Chicago
5 out of 5 average rating, 4 reviewsUp-scale co-living near UChicago | Unit 101 Room 5
Destinations to explore
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Holland Holiday rentals
- Saugatuck Holiday rentals
- South Side Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- Chicago Holiday rentals
- Smoking-friendly rentals Downtown Chicago
- Rentals with a hot tub Downtown Chicago
- Apartment rentals Downtown Chicago
- Rentals with an EV charger Downtown Chicago
- Waterfront rentals Downtown Chicago
- Rentals with beach access Downtown Chicago
- Rentals with breakfast Downtown Chicago
- Hotel rentals Downtown Chicago
- Fitness-friendly rentals Downtown Chicago
- Rentals with a washing machine and dryer Downtown Chicago
- Loft rentals Downtown Chicago
- Rentals with a cinema Downtown Chicago
- Rentals with a fireplace Downtown Chicago
- Townhouse rentals Downtown Chicago
- Rentals with lake access Downtown Chicago
- Rentals with a patio Downtown Chicago
- Rentals with a sauna Downtown Chicago
- House rentals Downtown Chicago
- Rentals with outdoor seating Downtown Chicago
- Family-friendly rentals Downtown Chicago
- Flat rentals Downtown Chicago
- Rentals with a firepit Downtown Chicago
- Pet-friendly rentals Downtown Chicago
- Rentals with pools Downtown Chicago
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club
- Things to do Downtown Chicago
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