
Vacation rentals in Chicago Loop
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Top-rated vacation rentals in Chicago Loop
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Vacation rentals for every style
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Popular amenities for Chicago Loop vacation rentals
Other great vacation rentals in Chicago Loop
Guest favorite

Apartment in Chicago
5 out of 5 average rating, 7 reviewsSunny Penthouse - Oakwood Beach
Superhost

Private room in River North
4.88 out of 5 average rating, 217 reviewsChicago Speakeasy-Style Loft (Room 2B)
Superhost

Apartment in The Loop
4.92 out of 5 average rating, 50 reviewsThe Areal Oasis
Guest favorite

Apartment in The Loop
5 out of 5 average rating, 17 reviewsThe Parkside Pavilion
Top guest favorite

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

Apartment in The Loop
5 out of 5 average rating, 15 reviewsPanoramic 2BR Penthouse in the Sky | Roof Deck
Superhost

Apartment in The Loop
4.69 out of 5 average rating, 49 reviewsSentral 1 Bedroom Apt in South Loop Chicago
Superhost

Hotel room in The Loop
5 out of 5 average rating, 3 reviewsNewly reno’d king room with sweet city views
Quick stats about vacation rentals in Chicago Loop
Total rentals
1.1K properties
Total number of reviews
28K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
610 properties allow pets
Rentals with a pool
540 properties have a pool
Rentals with dedicated workspaces
550 properties have a dedicated workspace
Destinations to explore
- Loft rentals Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with beach access Chicago Loop
- Kid-friendly rentals Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with a home theater Chicago Loop
- Rentals with a hot tub Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with lake access Chicago Loop
- Pet-friendly rentals Chicago Loop
- Waterfront rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with outdoor seating Chicago Loop
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- 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
- Illinois Beach State Park
- Brookfield Zoo
- Wicker Park
- Washington Park Zoo
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago Loop
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- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes