Holiday houses 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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Holiday rentals for every style
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Popular amenities for Chicago Loop holiday rentals
Other great holiday rentals in Chicago Loop
Guest favourite
Guesthouse in Wicker Park
4.96 out of 5 average rating, 25 reviewsSolar Victorian MCM Coach House
Guest favourite
Loft in West Loop
5 out of 5 average rating, 23 reviewsArtist Loft West Loop Restaurant Row
Superhost
Rental unit in Wicker Park
4.93 out of 5 average rating, 85 reviews【Central】- Eclectic Fun 1BR APT in Wicker Park
Superhost
Rental unit in The Loop
4.89 out of 5 average rating, 38 reviewsLoop Loft-Subway & Art Institute
Superhost
Rental unit in Gold Coast
4.84 out of 5 average rating, 44 reviewsMAG MILE/Gold Coast Getaway (+Rooftop/Gym)
Guest favourite
Rental unit in West Loop
5 out of 5 average rating, 8 reviewsChicago Luxury Long Term 30+
Guest favourite
Rental unit in West Town
4.95 out of 5 average rating, 19 reviewsNewly Remodeled in West Town
Guest favourite
Rental unit in Near North Side
4.93 out of 5 average rating, 75 reviews50th Floor Mag Mile Studio
Quick stats about holiday rentals in Chicago Loop
Total rentals
1K properties
Total number of reviews
25K reviews
Family-friendly rentals
270 properties are a good fit for families
Pet-friendly rentals
540 properties allow pets
Rentals with a pool
470 properties have a pool
Rentals with dedicated workspaces
650 properties have a dedicated workspace
Destinations to explore
- Rentals with a patio Chicago Loop
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- Monthly Rentals Chicago Loop
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- Family-friendly rentals Chicago Loop
- Rentals with a washing machine and dryer Chicago Loop
- Loft rentals Chicago Loop
- Rentals with pools Chicago Loop
- Apartment rentals Chicago Loop
- Rentals with an EV charger Chicago Loop
- Rentals with a sauna Chicago Loop
- Rentals with lake access Chicago Loop
- Rentals with a hot tub Chicago Loop
- Rentals with a fire pit Chicago Loop
- Fitness-friendly rentals Chicago Loop
- Hotel rentals Chicago Loop
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- Condo rentals Chicago Loop
- Rentals with a fireplace Chicago Loop
- Rentals with breakfast Chicago Loop
- Pet-friendly rentals Chicago Loop
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