Grand Beach Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Your Grand Beach Vacation
When you book a vacation package to Grand Beach, all the organizing is done in advance. This gives you plenty of time to uncover some of the best things about this serene city, such as its coastal scenery, laid-back lifestyle and spectacular views. Fill your free time with visits to Four Winds Casino New Buffalo, New Buffalo Public Beach and Michiana Beach, some of the top attractions you really should see during a trip to Grand Beach. Your ultimate Grand Beach vacation is just clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your style.
Top Grand Beach Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,066, price is now CA $1,229 per person
CA $1,229
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug. 29, 2025
Pendry Chicago
Downtown Chicago
Price was CA $1,375, price is now CA $820 per person
CA $820
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.
Reviewed on Aug. 26, 2025
The Emily Hotel
Downtown Chicago
Price was CA $2,190, price is now CA $1,400 per person
CA $1,400
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug. 22, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was CA $1,133, price is now CA $740 per person
CA $740
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (282 reviews)
The staff were excellent
Reviewed on Aug. 21, 2025
Grand Beach Hotel Deals
Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from Sep 4 to Sep 5
CA $147
CA $171 total
Sep 4 - Sep 5
includes taxes & fees
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Sep 2 to Sep 3
CA $124
CA $159 total
Sep 2 - Sep 3
includes taxes & fees
Pine Lake Resort and Banquets
444 Pine Lake Ave, La Porte, IN
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Aug 31 to Sep 1
CA $122
CA $141 total
Aug 31 - Sep 1
includes taxes & fees
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.