
Vacation rentals in Chicago Loop
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness, and more.
0 of 0 items showing
1 of 3 pages
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago Loop vacation rentals
Other great vacation rentals in Chicago Loop
Superhost

Apartment in The Loop
4.83 out of 5 average rating, 178 reviewsStunning Corner 2BR in the Loop | City & Lake View
Top guest favorite

Apartment in Chicago
5 out of 5 average rating, 17 reviewsSunny Penthouse - Oakwood Beach
Superhost

Hotel room in The Loop
4.83 out of 5 average rating, 72 reviewsSouth Loop Studio Hotel (305)
Guest favorite

Private room in River North
4.88 out of 5 average rating, 225 reviewsChicago Speakeasy-Style Loft (Room 2B)

Apartment in The Loop
4.7 out of 5 average rating, 138 reviewsCozy 1BR in South Loop | Convenience in the City
Top guest favorite

Private room in East Pilsen
5 out of 5 average rating, 128 reviewsUrban Oasis Pilsen - guest room in townhouse
Superhost

Apartment in The Loop
4.75 out of 5 average rating, 267 reviewsStunning 3BR Penthouse in the Loop | Roof Deck
Top guest favorite

Private room in West Town
4.95 out of 5 average rating, 39 reviewsStylish Condo BR w/Skyline Views – Walk Score 95
Quick stats about vacation rentals in Chicago Loop
Total rentals
1.1K properties
Nightly prices starting at
$40 before taxes and fees
Total number of reviews
28K reviews
Family-friendly rentals
300 properties are a good fit for families
Pet-friendly rentals
620 properties allow pets
Rentals with a pool
540 properties have a pool
Destinations to explore
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Boutique hotel rentals Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Condo rentals Chicago Loop
- Rentals with a home theater Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a washer and dryer Chicago Loop
- Rentals with a patio Chicago Loop
- Rentals with a hot tub Chicago Loop
- Waterfront rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Serviced apartment rentals Chicago Loop
- Rentals with beach access Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with a fire pit Chicago Loop
- Rentals with a sauna Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with outdoor seating Chicago Loop
- 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
- Illinois Beach State Park
- Washington Park Zoo
- Garfield Park Conservatory
- Wicker Park
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club
- Things to do Chicago Loop
- Things to do Chicago
- Sports activities Chicago
- Food and drink Chicago
- Tours Chicago
- Nature and outdoors Chicago
- Sightseeing Chicago
- Art and culture Chicago
- Things to do Cook County
- Sports activities Cook County
- Tours Cook County
- Sightseeing Cook County
- Art and culture Cook County
- Food and drink Cook County
- Things to do Illinois
- Sports activities Illinois
- Food and drink Illinois
- Sightseeing Illinois
- Nature and outdoors Illinois
- Art and culture Illinois
- Tours Illinois
- Things to do United States
- Tours United States
- Sports activities United States
- Food and drink United States
- Entertainment United States
- Sightseeing United States
- Wellness United States
- Nature and outdoors United States
- Art and culture United States
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- 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