Vacations Close To Dowagiac Four Winds Casino

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Dowagiac Four Winds Casino Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was $918, price is now $723 per person
$723
per person
Dec 24 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Everything was good for the price and super easy to go to the downtown

Reviewed on Nov 11, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was $1,606, price is now $1,102 per person
$1,102
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,576, price is now $1,136 per person
$1,136
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)

The Blackstone, Autograph Collection

The Blackstone, Autograph Collection

4 out of 5
Downtown Chicago
Price was $1,126, price is now $829 per person
$829
per person
Dec 24 - Dec 31
found 8 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,323, price is now $1,012 per person
$1,012
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Amazing great staff, very friendly front desk! Clean rooms and amazing views.

Reviewed on Nov 15, 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $1,080, price is now $829 per person
$829
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
A

Reviewed on Nov 12, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours.

Reviewed on Nov 14, 2026

The Den Hotel

The Den Hotel

2 out of 5
Lakeview
Price was $1,216, price is now $943 per person
$943
per person
Dec 24 - Jan 1
found 8 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)

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Best Lodging Options Near Dowagiac Four Winds Casino

LakeWood Inn & Suites

LakeWood Inn & Suites

2 out of 5
29291 Amerihost Dr Dowagiac MI
4.19 km from Dowagiac Four Winds Casino
Stay at this hotel in Dowagiac. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Beckwith Theatre and Dowagiac Area History Museum ...
The Morris Estate

The Morris Estate

4 out of 5
2007 Morris Dr Niles MI
15.34 km from Dowagiac Four Winds Casino
Stay at this B&B in Niles. Enjoy free WiFi, free parking, and conference space. Popular attractions FOP Park and Plym Park are located nearby.
Quality Inn & Suites Niles

Quality Inn & Suites Niles

2.5 out of 5
1265 S 11th St Niles MI
16.6 km from Dowagiac Four Winds Casino
Book a stay at this business-friendly hotel in Niles. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
The Grant Hotel and Venue

The Grant Hotel and Venue

2 out of 5
206 Days Ave Buchanan MI
21.51 km from Dowagiac Four Winds Casino
Stay at this hotel in Buchanan. Enjoy free WiFi, free parking, and a snack bar/deli. Popular attractions Firehouse Park and McCoy Creek Recreation Area are located ...
Wingate by Wyndham South Bend/Notre Dame

Wingate by Wyndham South Bend/Notre Dame

3 out of 5
52890 State Rt 933 N South Bend IN
25.94 km from Dowagiac Four Winds Casino
Stay at this hotel in South Bend. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. ...
La Quinta Suites by Wyndham South Bend Notre Dame Area

La Quinta Suites by Wyndham South Bend Notre Dame Area

3 out of 5
52554 STATE ROAD 933 South Bend IN
25.35 km from Dowagiac Four Winds Casino
Book a stay at this business-friendly hotel in South Bend. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
Irish Lodge South Bend

Irish Lodge South Bend

2.5 out of 5
52709 Indiana State Route 933 South Bend IN
25.65 km from Dowagiac Four Winds Casino
Book a stay at this business-friendly hotel in South Bend. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express & Suites Mishawaka - South Bend by IHG

Holiday Inn Express & Suites Mishawaka - South Bend by IHG

2.5 out of 5
224 FLORENCE AVE Granger IN
24.41 km from Dowagiac Four Winds Casino
Book a stay at this business-friendly hotel in Granger. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
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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.