Vacations Close To Shady Creek Winery

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Shady Creek Winery Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,153, price is now $841 per person
$841
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,401, price is now $1,437 per person
$1,437
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Everyone there was more than helpful. They went out of there way for us.

Reviewed on Oct 6, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,998, price is now $1,304 per person
$1,304
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Free upgrade was amazing and staff were even better. Thank you.

Reviewed on Oct 6, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,162, price is now $1,418 per person
$1,418
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
I had booked an Executive Room months in advanced and when I got there they gave me a much smaller room then I was expecting

Reviewed on Oct 4, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,285, price is now $844 per person
$844
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Ok

Reviewed on Oct 6, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,885, price is now $1,256 per person
$1,256
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,546, price is now $1,132 per person
$1,132
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,369, price is now $1,029 per person
$1,029
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Chicago (ORD)
Rooms were very clean and the staff was helpful in giving recommendations! Will stay again if i’m in Chicago again! A lot of places were walking distance. Perfect location

Reviewed on Oct 6, 2026

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Best Lodging Options Near Shady Creek Winery

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive Michigan City IN
5.38 km from Shady Creek Winery
Book a stay at this spa hotel in Michigan City. Enjoy free WiFi, a full-service spa, and 3 restaurants. Our guests praise the helpful staff and the clean rooms ...
The Brewery Lodge Hotel

The Brewery Lodge Hotel

3.5 out of 5
5727N 600W Michigan City IN
3.54 km from Shady Creek Winery
Book a stay at this business-friendly hotel in Michigan City. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
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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.