
Dowagiac Vacation Packages
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Your Dowagiac Vacation
Its friendly locals, small-town feel and rich history are only some of the reasons to book a vacation package to Dowagiac. Whatever brings you to this rural city, you're sure to have a great time. Up for a bit of sightseeing? A trip to Dowagiac wouldn't be complete without checking out Dowagiac Four Winds Casino, Southwestern Michigan College and other major attractions. Whoever you're taking a break with and whatever the size of your budget, your dream Dowagiac vacation is just a few clicks away with Expedia.
Top Dowagiac Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was CA $1,509, price is now CA $1,013 per person
CA $1,013
per person
May 11 - May 15
found 23 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was CA $1,830, price is now CA $1,190 per person
CA $1,190
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors.
Reviewed on Mar 27, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,728, price is now CA $1,209 per person
CA $1,209
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Just an amazing place to stay. The staff is lovely, the rooms are wonderful and the location is perfect for a day at the waterline.
Reviewed on Mar 27, 2026

Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,761, price is now CA $1,307 per person
CA $1,307
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on Mar 9, 2026

Hotel Arista
Price was CA $1,425, price is now CA $1,058 per person
CA $1,058
per person
Jun 3 - Jun 9
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
Our room was spacious, clean and well appointed. I love a bathroom with good lighting and the tv in the vanity mirror was fantastic to catch the morning news as we got ready!!
The staff was exceptional. From check in, to drinks at the bar, to room service, everyone was incredibly friendly and professional. I highly recommend Hotel Arista.
Reviewed on Mar 24, 2026
Dowagiac Hotel Deals

LakeWood Inn & Suites
29291 Amerihost Dr Dowagiac MI
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Apr 4 to Apr 5
CA $117
CA $124 total
Apr 4 - Apr 5
includes taxes & fees
7.2/10 Good! (68 reviews)
The staff forgot to put a blanket or comforter on our bed. Went to the front desk and they had a sign on the counter to call this number if no one was there. I wanted to talk to someone from the staff to make sure that they knew what was missing. In retrospect I wanted to make sure that I wouldn’t ...
Reviewed on Mar 2, 2026

Four Winds Casino South Bend
3000 Prairie Ave South Bend IN
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Mar 31 to Apr 1
CA $123
CA $154 total
Mar 31 - Apr 1
includes taxes & fees
9.6/10 Exceptional! (889 reviews)
First time spending the night. We had a junior sweet that was amazing. Look forward to returning again soon.
Reviewed on Mar 25, 2026

The Boulevard Inn & Bistro
521 Lake Blvd Saint Joseph MI
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Mar 29 to Mar 30
CA $185
CA $206 total
Mar 29 - Mar 30
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
Great location in St. Joseph! Fantastic room at a great rate for the off season. The breakfast was most of the usual fare but was lacking in protein options one of the days. We had an excellent dinner at the Bistro.
Reviewed on Mar 26, 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.







