Sawyer Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Sawyer Vacation
Food, history, entertainment and more … There's so much to discover with a Sawyer vacation package. And with the ability to easily customize your city getaway, it's guaranteed to be one that's tough to forget. Fill your schedule with tours of Warren Dunes State Park Beach, Cherry Beach and Round Barn Union Pier Tasting Room, some of the things you simply have to see during a trip to Sawyer. Don't put off exploring this city any longer. The perfect Sawyer vacation is a few clicks away with Expedia.
Top Sawyer Vacation Deals
Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago
Downtown Chicago
Price was CA $1,039, price is now CA $707 per person
CA $707
per person
May 1 - May 3
found 2 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Bottle of waters were not stocked in the refrigerator.
Reviewed on Jan 6, 2026
La Banque Hotel
Price was CA $1,044, price is now CA $743 per person
CA $743
per person
Apr 9 - Apr 12
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Aloft Chicago Downtown River North
Downtown Chicago
Price was CA $1,064, price is now CA $778 per person
CA $778
per person
Mar 31 - Apr 4
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Room and customer service was great!
Reviewed on Jan 20, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,209, price is now CA $885 per person
CA $885
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Staff was friendly, and room was cleaned well. Free breakfast was also a nice touch and better than expected
Reviewed on Feb 6, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,950, price is now CA $1,433 per person
CA $1,433
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Sawyer Hotel Deals
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Mar 2 to Mar 3
CA $172
CA $215 total
Mar 2 - Mar 3
includes taxes & fees
8.2/10 Very Good! (1,932 reviews)
Overall experience was great.
Reviewed on Feb 2, 2026
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Feb 8 to Feb 9
CA $110
CA $127 total
Feb 8 - Feb 9
includes taxes & fees
9.2/10 Wonderful! (1,676 reviews)
Rooms were perfect. Staff friendly. Had to stay an extra night due to weather staff allowed us to stay in the room we had been in. Restaurants were good would stay again!
Reviewed on Jan 29, 2026
The Inn at Saint Mary's
53993 Indiana State Route 933 South Bend IN
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Feb 10 to Feb 11
CA $126
CA $145 total
Feb 10 - Feb 11
includes taxes & fees
9.4/10 Exceptional! (1,136 reviews)
Cleaning agent very strong.
Reviewed on Feb 5, 2026
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.
