
Holiday rentals in Chicago Loop
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Top-rated holiday rentals in Chicago Loop
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Chicago Loop holiday rentals
Other great holiday rentals in Chicago Loop
Superhost

Home in West Lawn
4.95 out of 5 average rating, 37 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
AshleyRating, 5 stars3 weeks ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favourite

Home in Elmhurst
4.86 out of 5 average rating, 22 reviewsEnamored in Elmhurst
YvonneRating, 5 stars2 weeks ago
This home is in a beautiful neighborhood. It was very clean and the decor was simple yet stunning. There was plenty of linen and the kitchen was stocked well enough to cook an entire meal Mark was very responsive and provided clear instructions for check in and out. I would stay here again
Guest favourite

Flat in West Town
4.85 out of 5 average rating, 128 reviewsCondo with private terrace, free WIFI and parking
OlegRating, 5 stars1 month ago
We have traveled to Chicago with a party of 5 - 3 adults and 2 kids in February 2025. We stayed for 3 nights and really liked Mark's place. It is really bigger than it shows on the pictures, so it really accomodates 6-8 people easily. Host was responsive and provided helpful and timely instructions. Would stay again.
Guest favourite

Flat in Albany Park
4.86 out of 5 average rating, 42 reviewsElegant 4Bedroom with Free Parking in Albany Park
MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost

Flat in Jefferson Park
4.65 out of 5 average rating, 23 reviewsCity Gem: Stylish 3BR for Urban Explorers
AnnikaRating, 5 stars2 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost

Apartment in East Rogers Park
4.79 out of 5 average rating, 29 reviewsSpacious condo with open floor plan and fireplace
TatianaRating, 5 stars3 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Superhost

Home in Cicero
4.79 out of 5 average rating, 177 reviewsSpacious whole apt near shopping and city
AdedolapoRating, 5 stars1 week ago
Beautiful and excellent place host was very helpful
Top guest favourite

Home in Lombard
5 out of 5 average rating, 24 reviewsSpacious Home in Chicago Suburbs
KimberlyRating, 5 stars3 weeks ago
Great place! It was easy to get in and out of. The host was very responsive! We would definitely stay again.
Quick stats about holiday rentals in Chicago Loop
Total rentals
1.1K properties
Total number of reviews
27K reviews
Family-friendly rentals
290 properties are a good fit for families
Pet-friendly rentals
610 properties allow pets
Rentals with a pool
510 properties have a pool
Rentals with dedicated workspaces
670 properties have a dedicated workspace
Destinations to explore
- Rentals with beach access Chicago Loop
- Rentals with an EV charger Chicago Loop
- Loft rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Rentals with outdoor seating Chicago Loop
- Fitness-friendly rentals Chicago Loop
- House rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with a firepit Chicago Loop
- Apartment rentals Chicago Loop
- Family-friendly rentals Chicago Loop
- Rentals with a sauna Chicago Loop
- Flat rentals Chicago Loop
- Rentals with lake access Chicago Loop
- Waterfront rentals Chicago Loop
- Hotel rentals Chicago Loop
- Rentals with pools Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with a cinema Chicago Loop
- Pet-friendly rentals Chicago Loop
- Rentals with breakfast Chicago Loop
- Rentals with a patio Chicago Loop
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- The Field Museum
- Lincoln Park Zoo
- Six Flags Great America
- Promontory Point
- Museum of Science and Industry
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Villa Olivia
- Raging Waves Waterpark
- Moraine Hills State Park
- Washington Park Zoo
- Things to do Chicago Loop
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