Vacations Close To Sleeping Village

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Sleeping Village Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $850, price is now $667 per person
$667
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,708, price is now $1,744 per person
$1,744
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,368, price is now $916 per person
$916
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Great property!! Beautiful rooftop bar!!

Reviewed on Oct 19, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $1,150, price is now $807 per person
$807
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Clean room. Valet service slow.

Reviewed on Oct 18, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,355, price is now $978 per person
$978
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop

Reviewed on Oct 19, 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was $965, price is now $743 per person
$743
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Had a great night in a great room!

Reviewed on Oct 18, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,110, price is now $864 per person
$864
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
I found a parking spot in 303 wacker. The building next door off of spothero for 18 dollars a day. It’s tough to get to because it’s on lower Columbus but you come out right next door to the hotel

Reviewed on Oct 19, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,151, price is now $902 per person
$902
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Always a great stay at Eurostars, excellent location

Reviewed on Oct 18, 2026

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Best Lodging Options Near Sleeping Village

The Hotel at Midtown

The Hotel at Midtown

4 out of 5
2444 N. Elston Ave Chicago IL
3.81 km from Sleeping Village
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
Ray's Bucktown B&B

Ray's Bucktown B&B

3.5 out of 5
2144 N. Leavitt St Chicago IL
3.77 km from Sleeping Village
Book a stay at this business-friendly B&B in Chicago. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.