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Parking
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Pool
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Balcony/Terrace
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Kitchen

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 West Side offers world-class resort destinations for every travel style, season, and budget.
Guests
- Hotels
- Villas
- Cabins
- Rentals
- Cottages
- Resorts
- Accommodations
- Chicago
- ·
- Illinois Medical District
- 0.33 mi to center
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Private Pool
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Breakfast
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Parking
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Pool
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Private Pool
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Breakfast
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Parking
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Pool
- Chicago
- ·
- Illinois Medical District
- 0.32 mi to center
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Breakfast
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Parking
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Pool
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Kitchen
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Breakfast
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Parking
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Pool
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Kitchen
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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
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Kitchen
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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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Balcony/Terrace
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Kitchen
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Air Conditioner
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Internet
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Pool
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Pool
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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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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
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Kitchen
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Pool
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Balcony/Terrace
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Kitchen
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Air Conditioner
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Pool
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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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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
- Chicago
- ·
- River West
- 0.33 mi to center
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Air Conditioner
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Internet
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Accessibility
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Bedding/Linens
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Air Conditioner
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Internet
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Accessibility
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Bedding/Linens
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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
-
Air Conditioner
- Chicago
- ·
- East Garfield Park
- 0.60 mi to center
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Parking
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Internet
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Child Friendly
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Security/Safety
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Parking
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Internet
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Child Friendly
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Security/Safety
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Breakfast
-
Kitchen
-
Air Conditioner
-
Internet
-
Breakfast
-
Kitchen
-
Air Conditioner
-
Internet
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Parking
-
Kitchen
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Air Conditioner
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Internet
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Parking
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Kitchen
-
Air Conditioner
-
Internet
- Chicago
- ·
- Near West Side
- 0.34 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
-
Internet
- Chicago
- ·
- Near West Side
- 0.15 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
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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
-
Air Conditioner
- Chicago
- ·
- East Garfield Park
- 0.60 mi to center
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Parking
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Internet
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Child Friendly
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Security/Safety
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Parking
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Internet
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Child Friendly
-
Security/Safety
-
Breakfast
-
Kitchen
-
Air Conditioner
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Internet
-
Breakfast
-
Kitchen
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Air Conditioner
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Internet
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Parking
-
Kitchen
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Air Conditioner
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Internet
-
Parking
-
Kitchen
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Air Conditioner
-
Internet
- Chicago
- ·
- Near West Side
- 0.34 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
-
Internet
- Chicago
- ·
- Near West Side
- 0.15 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- East Garfield Park
- 0.60 mi to center
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Parking
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Internet
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Child Friendly
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Security/Safety
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Parking
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Internet
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Child Friendly
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Security/Safety
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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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Breakfast
-
Kitchen
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Air Conditioner
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Internet
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Breakfast
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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
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
- ·
- Near West Side
- 0.34 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
- ·
- Near West Side
- 0.15 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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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
- Chicago
- ·
- East Garfield Park
- 0.60 mi to center
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Parking
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Internet
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Child Friendly
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Security/Safety
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Parking
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Internet
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Child Friendly
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Security/Safety
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Breakfast
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Kitchen
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Air Conditioner
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Internet
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Breakfast
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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
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Parking
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Kitchen
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Air Conditioner
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Internet
- Chicago
- ·
- Near West Side
- 0.34 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
- ·
- Near West Side
- 0.15 mi to center
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Parking
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Ocean View
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View
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Kitchen
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Parking
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Ocean View
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View
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
Find the Perfect Resort Vacation in the West Side
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 West Side
What are the Top Resort Locations Across the West Side?
Discover resorts in the most sought-after travel destinations nationwide:
Near West Side
Near West Side VACATION RENTALSWest Town
West Town VACATION RENTALSWest Loop
West Loop VACATION RENTALSEast Village
East Village VACATION RENTALSUniversity Village / Little Italy
University Village / Little Italy VACATION RENTALSLower West Side
Lower West Side VACATION RENTALSRiver West
River West VACATION RENTALSHeart of Chicago
Heart of Chicago VACATION RENTALSWest Loop Gate
West Loop Gate VACATION RENTALSWicker Park
Wicker Park VACATION RENTALSPulaski Park
Pulaski Park VACATION RENTALSNoble Square
Noble Square VACATION RENTALSHow to Reserve Your Resorts Vacation Accommodation?
Booking Made Simple
Resorts Vacations connects travelers with verified resort stays from trusted partners across the West Side. 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 West Side
What Amenities Can You Expect When Booking with Resorts Vacations?
Resorts Vacations offers carefully selected resort stays across the West Side, 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 West Side? 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
- ·
- Near West Side
- 0.34 mi to center
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Parking
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Kitchen
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Air Conditioner
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Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
- Chicago
- ·
- Near West Side
- 0.15 mi to center
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Parking
-
Ocean View
-
View
-
Kitchen
-
Parking
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Ocean View
-
View
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.23 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
-
Hot Tub
-
Parking
-
Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Ukrainian Village
- 0.13 mi to center
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
-
Kitchen
- Chicago
- ·
- Near West Side
- 0.15 mi to center
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Parking
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Ocean View
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View
-
Kitchen
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Parking
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Ocean View
-
View
-
Kitchen
- Chicago
- ·
- Wicker Park
- 0.14 mi to center
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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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Spa
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Balcony/Terrace
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Hot Tub
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Parking
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Spa
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Balcony/Terrace
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Parking
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Ocean View
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Balcony/Terrace
-
View
-
Parking
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Ocean View
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Balcony/Terrace
-
View
- Chicago
- ·
- Noble Square
- 0.13 mi to center
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Parking
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Balcony/Terrace
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View
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Kitchen
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Parking
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Balcony/Terrace
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View
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Kitchen
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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
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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Hot Tub
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Parking
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Balcony/Terrace
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Kitchen
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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
-
Air Conditioner
Resorts Vacations FAQs
How many vacation rentals have private pools in West Side?
There are 6 vacation rentals with private pools near West Side. Top-rated homes that have access to a swimming pool include:
Which vacation homes in West Side are best for families?
If you are looking for a family-friendly vacation home in West Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in West Side:
How many vacation rentals are available in West Side?
Currently, the total number of properties listed in 2026 is over 1640 in the West Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in West Side.
More Resorts Vacations to Explore
- Chicago
- ·
- East Garfield Park
- 0.60 mi to center
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Parking
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Internet
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Child Friendly
-
Security/Safety
-
Parking
-
Internet
-
Child Friendly
-
Security/Safety
- Chicago
- ·
- East Garfield Park
- 0.75 mi to center
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Parking
-
View
-
Air Conditioner
-
Internet
-
Parking
-
View
-
Air Conditioner
-
Internet
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
-
Air Conditioner
-
Internet
-
Security/Safety
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Guest Services
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Parking
-
Kitchen
-
Air Conditioner
-
Internet
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
- Chicago
- ·
- Tri-Taylor
- 0.28 mi to center
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Air Conditioner
-
Internet
-
Security/Safety
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Air Conditioner
-
Internet
-
Security/Safety
- Chicago
- ·
- East Garfield Park
- 0.43 mi to center
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Kitchen
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Air Conditioner
-
Internet
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Pet Friendly
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Kitchen
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Air Conditioner
-
Internet
-
Pet Friendly
- Chicago
- ·
- East Village
- 0.16 mi to center
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Air Conditioner
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Internet
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Security/Safety
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Guest Services
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Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
- Chicago
- ·
- Ukrainian Village
- 0.41 mi to center
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Air Conditioner
-
Internet
-
Accessibility
-
Security/Safety
-
Air Conditioner
-
Internet
-
Accessibility
-
Security/Safety
- Chicago
- ·
- Ukrainian Village
- 0.28 mi to center
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Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
-
Air Conditioner
-
Internet
-
Security/Safety
-
Guest Services
- Chicago
- ·
- River West
- 0.13 mi to center
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Air Conditioner
-
Internet
-
Accessibility
-
Security/Safety
-
Air Conditioner
-
Internet
-
Accessibility
-
Security/Safety