Vacations Close To Lake Michigan
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Lake Michigan Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
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)
Great location. Couldn’t go to rooftop due to weather. No ice machine
Reviewed on Oct 6, 2026
Trump International Hotel & Tower Chicago
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 24 hours 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
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
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)
Me gustó mucho toda la gente fue súper amable, lo único que no me encantó fue que no me avisaron que no hacían limpieza a la habitación.
Reviewed on Oct 6, 2026
Silversmith Hotel Chicago Downtown
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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View all tripsBest Lodging Options Near Lake Michigan
Blue Harbor Resort and Conference Center
725 Blue Harbor Drive Sheboygan WI
51.11 km from Lake Michigan
Book a stay at this beach resort in Sheboygan. Enjoy free WiFi, an outdoor pool, and a full-service spa. Popular attractions Blue Harbor Resort & Conference ...
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
72.23 km from Lake Michigan
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Four Points by Sheraton Milwaukee North Shore
8900 N Kildeer Ct Milwaukee WI
66.78 km from Lake Michigan
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Sybaris Pool Suites Mequon
10240 Cedarburg Rd, Hwy. 57 Mequon WI
66.36 km from Lake Michigan
Stay at this hotel in Mequon. Enjoy free WiFi, free parking, and private hot tubs. Popular attractions Walter Schroeder Aquatic Center and Lynden Sculpture Garden ...
Drury Plaza Hotel Milwaukee Downtown
700 N. Water Street Milwaukee WI
72.02 km from Lake Michigan
Book a stay at this business-friendly hotel in Milwaukee. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and ...
Motel 6 Milwaukee, WI - Glendale
5485 N Port Washington Rd Milwaukee WI
67.38 km from Lake Michigan
Stay at this motel in Milwaukee. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.