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

Home in West Lawn
4.92 out of 5 average rating, 38 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
AshleyRating, 5 stars4 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 stars3 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

Apartment 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

Apartment 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

Apartment 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

Condo 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, 25 reviewsSpacious Home in Chicago Suburbs
JenniferRating, 5 stars1 day ago
It was great! The house was lovely and looked newly renovated. It was much roomier than I expected. The beds were very comfortable.
Quick stats about vacation rentals in South Loop, Chicago
Total rentals
460 properties
Nightly prices starting at
$42 CAD before taxes and fees
Total number of reviews
22K reviews
Family-friendly rentals
260 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with a pool
120 properties have a pool
Destinations to explore
- Apartment rentals South Loop
- Pet-friendly rentals South Loop
- Rentals with outdoor seating South Loop
- Smoking-friendly rentals South Loop
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- Rentals with a fireplace South Loop
- Rentals with a firepit South Loop
- Rentals with a washer and dryer South Loop
- Fitness-friendly rentals South Loop
- Rentals with lake access South Loop
- Rentals with a patio South Loop
- Rentals with an EV charger South Loop
- Rentals with a hot tub South 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
- Museum of Science and Industry
- Promontory Point
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Splash Station
- Flossmoor Golf Club
- Raging Waves Waterpark
- Moraine Hills State Park
- Villa Olivia
- Chicago History Museum