Dowagiac Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,106, price is now CA $794 per person
CA $794
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,284, price is now CA $938 per person
CA $938
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Ready to book your vacation to Dowagiac?

 

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Dowagiac Hotel Deals

LakeWood Inn & Suites

LakeWood Inn & Suites

2 out of 5
29291 Amerihost Dr Dowagiac MI
Fully refundableReserve now, pay when you stay
The price is CA $59 per night from Nov 23 to Nov 24
CA $59
CA $63 total
Nov 23 - Nov 24
includes taxes & fees
LakeWood Inn & Suites
Silver Beach Hotel

Silver Beach Hotel

3.5 out of 5
100 Main Street Saint Joseph MI
Fully refundableReserve now, pay when you stay
The price is CA $113 per night from Nov 15 to Nov 16
CA $113
CA $131 total
Nov 15 - Nov 16
includes taxes & fees
Silver Beach Hotel
Four Winds Casino South Bend

Four Winds Casino South Bend

3 out of 5
3000 Prairie Ave South Bend IN
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Nov 16 to Nov 17
CA $126
CA $157 total
Nov 16 - Nov 17
includes taxes & fees
9.6/10 Exceptional! (1,304 reviews)
"The room was very spacious and clean. Would highly recommend this hotel.,"

Reviewed on Nov 11, 2026

Four Winds Casino South Bend
See all 2,033 properties in Dowagiac
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.
All Inclusive Vacations
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Stay near popular Dowagiac attractions

A lake surrounded by dense forest and small buildings.

Magician Lake

10.0/10 (1 review)
Commune with nature and explore the great outdoors at Magician Lake during your travels in Sister Lakes.
See properties

Frequently asked questions

How much does a Dowagiac vacation package cost?
You'll find cheap prices from CA $671 on Expedia for your Dowagiac escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Dowagiac costs.
What are the cheapest months to go to Dowagiac?
Plan your trip for the off-peak season and you're likely to find cheap Dowagiac vacation packages. Remember that school vacation periods and major local events can have an impact on prices, so do a little research before you go.
How many days is enough for Dowagiac?
With a well-planned itinerary, you can easily hit the most popular Dowagiac sights in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Dowagiac vacation for longer.
How to find the best Dowagiac package deals?
Start your search for a Dowagiac package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Popular locations" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Dowagiac package deal straight away, simply change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Dowagiac escape off to a flying start.
Is it cheaper to book a Dowagiac vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights separately. Better still, you can customize your Dowagiac getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Dowagiac?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Dowagiac vacation.
How to plan a trip to Dowagiac?

  1. Pick your travel dates: What you plan to do in Dowagiac and your favourite season can help you decide when to get away.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Dowagiac.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Dowagiac. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Dowagiac vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.