
Discover the Best Resort Vacations
Explore the top resorts, from luxury beachfront escapes to family-friendly all-inclusive resorts and relaxing spa retreats. Whether you’re planning a weekend getaway or an extended vacation, the The Loop offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Chicago
- ·
- Downtown Chicago
- 0.25 mi to center
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Private Pool
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EV Charge Station
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Parking
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Pool
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Private Pool
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EV Charge Station
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Parking
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Pool
- Chicago
- ·
- Downtown Chicago
- 0.20 mi to center
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Hot Tub
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Breakfast
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Parking
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Pool
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Hot Tub
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Breakfast
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Parking
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Pool
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
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Hot Tub
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Parking
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Kitchen
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Air Conditioner
- Chicago
- ·
- Downtown Chicago
- 0.21 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
- ·
- Downtown Chicago
- 0.33 mi to center
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Balcony/Terrace
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Air Conditioner
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Internet
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Child Friendly
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Balcony/Terrace
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Air Conditioner
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Internet
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Child Friendly
- Chicago
- ·
- Downtown Chicago
- 0.21 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Ocean View
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View
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Parking
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Pool
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Ocean View
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View
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
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Parking
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Pool
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Air Conditioner
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Internet
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Parking
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Pool
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Air Conditioner
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Internet
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Air Conditioner
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Internet
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Child Friendly
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Wheelchair Accessible
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Air Conditioner
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Internet
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Child Friendly
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Wheelchair Accessible
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Parking
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Pool
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Ocean View
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Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.43 mi to center
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Child Friendly
-
Child Friendly
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Ocean View
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View
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Parking
-
Pool
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Ocean View
-
View
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
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Parking
-
Pool
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Air Conditioner
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Internet
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Parking
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Pool
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Air Conditioner
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Internet
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Air Conditioner
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Internet
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Child Friendly
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Wheelchair Accessible
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Air Conditioner
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Internet
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Child Friendly
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Wheelchair Accessible
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
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Parking
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Pool
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Ocean View
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Balcony/Terrace
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Parking
-
Pool
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Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Balcony/Terrace
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Kitchen
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Parking
-
Pool
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.43 mi to center
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
-
Ocean View
-
View
-
Parking
-
Pool
-
Ocean View
-
View
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
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Parking
-
Pool
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Air Conditioner
-
Internet
-
Parking
-
Pool
-
Air Conditioner
-
Internet
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Air Conditioner
-
Internet
-
Child Friendly
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Wheelchair Accessible
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Air Conditioner
-
Internet
-
Child Friendly
-
Wheelchair Accessible
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
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Pool
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Balcony/Terrace
-
Kitchen
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Parking
-
Pool
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.43 mi to center
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Parking
-
Pool
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Ocean View
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Balcony/Terrace
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Breakfast
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Parking
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Child Friendly
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Laundry
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Air Conditioner
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Internet
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Child Friendly
-
Laundry
- Chicago
- ·
- Downtown Chicago
- 0.17 mi to center
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Air Conditioner
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Internet
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Child Friendly
- Chicago
- ·
- Downtown Chicago
- 0.53 mi to center
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Parking
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Air Conditioner
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Wheelchair Accessible
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Accessibility
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Parking
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Air Conditioner
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Wheelchair Accessible
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Accessibility
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
-
Ocean View
-
View
-
Parking
-
Pool
-
Ocean View
-
View
- Chicago
- ·
- Downtown Chicago
- 0.91 mi to center
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Parking
-
Pool
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Air Conditioner
-
Internet
-
Parking
-
Pool
-
Air Conditioner
-
Internet
-
Air Conditioner
-
Internet
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Child Friendly
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Wheelchair Accessible
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Air Conditioner
-
Internet
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Child Friendly
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Wheelchair Accessible
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.42 mi to center
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
- Chicago
- ·
- Downtown Chicago
- 0.41 mi to center
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Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
-
Parking
-
Pool
-
Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Downtown Chicago
- 0.43 mi to center
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Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Parking
-
Pool
-
Ocean View
-
Balcony/Terrace
-
Breakfast
-
Parking
-
Balcony/Terrace
-
Kitchen
-
Breakfast
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Parking
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Balcony/Terrace
-
Kitchen
Find the Perfect Resort Vacation in the The Loop
What makes our resorts stand out?
Verified Properties
Every vacation home shown on Resort Vacation comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Popular Resort Destinations in the The Loop
What are the Top Resort Locations Across the The Loop?
Discover resorts in the most sought-after travel destinations nationwide:
Chicago
Chicago VACATION RENTALSPrinters Row
Printers Row VACATION RENTALS333 West Wacker Drive
333 West Wacker Drive VACATION RENTALSLakeshore East
Lakeshore East VACATION RENTALSNear East Side
Near East Side VACATION RENTALSCivic Opera House
Civic Opera House VACATION RENTALSCadillac Palace Theatre
Cadillac Palace Theatre VACATION RENTALSChicago City Hall
Chicago City Hall VACATION RENTALSWillis Tower
Willis Tower VACATION RENTALSChicago
Chicago VACATION RENTALSCentral Chicago
Central Chicago VACATION RENTALSDowntown Chicago
Downtown Chicago VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the The Loop. Once you find the perfect resort, you’ll be seamlessly guided to our partner’s secure booking platform to complete your reservation with confidence.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Common Resort Vacation Amenities in the The Loop
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the The Loop, designed for comfort, convenience, and memorable experiences.
Indoor Amenities
Spacious guest rooms and suites
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Places to Stay with Resorts Vacations
Looking for the perfect resort vacation in the The Loop? Discover a curated collection of resort stays offering comfort, convenience, and unforgettable experiences in top destinations nationwide. Whether you’re searching for a beachfront resort, a family-friendly escape, or a luxury retreat, Resorts Vacations makes it easy to explore and compare verified resort options for your next getaway.
- Chicago
- ·
- Downtown Chicago
- 0.17 mi to center
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Parking
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Air Conditioner
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Internet
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Child Friendly
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Air Conditioner
-
Internet
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Child Friendly
-
Laundry
-
Air Conditioner
-
Internet
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Child Friendly
-
Laundry
- Chicago
- ·
- Downtown Chicago
- 0.53 mi to center
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Parking
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Air Conditioner
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Wheelchair Accessible
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Accessibility
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Parking
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Air Conditioner
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Wheelchair Accessible
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Accessibility
Resorts Vacations FAQs
What are the top vacation rentals in The Loop?
There are a lot of options in The Loop. If you plan on staying in the The Loop area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in The Loop:
- Sports Illustrated Resorts Chicago
- Boutique King Room at Hotel Blake Near Millennium Park & Willis Tower
- A Place You'll Surely Enjoy! Close to Chicago Vietnam Veterans Memorial
- Your Relaxing Getaway Awaits! 4 Posh Units, Pets Allowed, Near Picasso Statue
- Visit Chicago! 4 Modern Units near 360 Chicago and Oak Street Beach! Parking!
- Better Choice for your Vacation! 3 Convenient Units, Close to Chicago Riverwalk
- Vacation Day Is Always A Great Idea! Pets are Allowed, Near The River Theater
- Always a Great Idea To Unwind! Near Chicago Tribune Tower, Pets are Allowed
- Indulge in Home-Like Comfort! Near Bridgehouse and Chicago River Museum
- Vacation Starts Here! Near Chicago Riverwalk and The River Theater, Pets Allowed
How many vacation rentals have private pools in The Loop?
There are 25 vacation rentals with private pools near The Loop. Top-rated homes that have access to a swimming pool include:
Which vacation homes in The Loop are best for families?
If you are looking for a family-friendly vacation home in The Loop, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in The Loop:
How many vacation rentals are available in The Loop?
Currently, the total number of properties listed in 2026 is over 10 in the The Loop area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Loop.
More Resorts Vacations to Explore
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Air Conditioner
-
Internet
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Child Friendly
-
Laundry
-
Air Conditioner
-
Internet
-
Child Friendly
-
Laundry
- Chicago
- ·
- Downtown Chicago
- 0.17 mi to center
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
-
Parking
-
Air Conditioner
-
Internet
-
Child Friendly
- Chicago
- ·
- Downtown Chicago
- 0.53 mi to center
-
Parking
-
Air Conditioner
-
Wheelchair Accessible
-
Accessibility
-
Parking
-
Air Conditioner
-
Wheelchair Accessible
-
Accessibility