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
Popular stays in The Gap
Start where you want to be in The Gap. Then compare space, amenities and style.
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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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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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Air Conditioner
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Internet
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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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Private Pool
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Hot Tub
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EV Charge Station
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Parking
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EV Charge Station
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Parking
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Air Conditioner
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Internet
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EV Charge Station
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Parking
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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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Air Conditioner
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Internet
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:
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Modern 4BR Pilsen Retreat Near Illinois Medical District & Chicago Downtown
- Chicago 2BR Skyline Views - 5 Min walk to Grant Park
- Prime Chicago 2BR Skyline - 5 Min to Museum Campus
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- 21st Floor Skyline 2BR Near Grant Park & Field Museum
- McCormick Place 2BR Spacious Corner Unit with Optional Parking Sleeps 6 Guests Near Soldier Field and Grant Park
- McCormick Place Modern 2BR Loft in Downtown Chicago Michigan Avenue with Optional Parking Near Soldier Field
- Group Friendly Spacious 3BR Suite with Optional Parking and Gym Access Sleeps 10 Guest Near McCormick Place and Soldier Field
- Modern Chicago 2BR Skyline - 5 Min to Grant Park
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 75 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.