Stay well, then step out and discover The Gap.
Best Stays by Sonder
The Gap
Find places to stay in The Gap. Choose from apartment-style stays and boutique hotels for weekend breaks, business trips, and longer city stays.
Travelers
The nearest stays, ranked by walk time.
Start with the best-placed stays in The Gap, then compare the details that matter — space, style, and which neighborhood you want to land on after dinner.
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Close to everything worth your time.
Stay genuinely central in The Gap when you want dinner, sights, and the best neighborhoods within an easy walk, without sorting through places too far from the reason you came.
Sonder hasn't arrived in The Gap yet. You may like these stays from trusted partners
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Hot Tub
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Parking
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Pool
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Balcony/Terrace
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Parking
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Balcony/Terrace
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Air Conditioner
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Internet
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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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Private Pool
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Hot Tub
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EV Charge Station
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Parking
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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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Air Conditioner
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Internet
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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
The Gap answers before you book.
There are a lot of options in The Gap. If you plan on staying in the The Gap 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 Gap:
- 4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Dtown Penthouse 11+Parking, Gym, Pvt Patio
- Downtown 3bd #7 near Park+Museums
- Downtown Chicago Stay with Free In & Out Parking 3
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
- Downtown 3bd Penthouse| Lake Mich VIEWS +gym
- The En Bronze ~ 7mins To Dining & Downtown Chicago
There are 4 vacation rentals with private pools near The Gap. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in The Gap, 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 Gap:
Currently, the total number of properties listed in 2026 is over 200 in the The Gap area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in The Gap.