Name: Four Winds Casino Resort – New Buffalo
Price range: CA $164
Rating: 9.4

Your Lakeside Vacation

With a Lakeside vacation package, say goodbye to travel planning and hello to an effortless adventure. Every detail of your journey has been taken care of before you depart, so you can make the most of your time discovering this exciting city. Fill your schedule with tours of Four Winds Casino New Buffalo, New Buffalo Public Beach and Warren Dunes State Park Beach, some of the attractions you shouldn't miss during a trip to Lakeside. Browse Expedia's wide range of travel options and start planning your dream vacation to Lakeside today.

Top Lakeside Vacation Deals

Price found within the past 48 hours. Click for updated prices.

The Talbott, Autograph Collection

Downtown Chicago

CA $892

per person

Aug 31 - Sep 4

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (120 reviews)

The hotel is fresh and clean. Very nice facility. Staff anre wonderful. Only comment is there should be free water in the rooms, at least for Marriott members. For the rates charged, water should be included. Water pressure is a bit low.

Reviewed on Jun 21, 2026

Hotel Felix River North/Magnificent Mile

Downtown Chicago

CA $997

per person

Sep 18 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Montreal (YMQ) to Chicago (ORD)

8.2/10 Very good! (2,767 reviews)

Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience. I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.

Reviewed on Jun 22, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

CA $1,689

per person

Sep 14 - Sep 17

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,557 reviews)

You had to pay extra for the amenities like wifi and parking. Parking is outrageous while staying at the Pier, $60+ a day, $57 after 4 hours of parking. The elevators were out in our building so we had to carry our heavy bags up to the 3rd floor. The only thing I'd say that stuck out that were good was the location and the view from our room was nice.

Reviewed on Jun 23, 2026

Level Chicago Fulton Market

Downtown Chicago

CA $1,478

per person

Aug 15 - Aug 20

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (498 reviews)

The place was serene,close proximity to Fulton market and had amazing views

Reviewed on Jun 22, 2026

Omni Chicago Hotel

Downtown Chicago

CA $1,257

per person

Aug 15 - Aug 20

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Chicago (ORD)

9.2/10 Wonderful! (1,813 reviews)

Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable

Reviewed on Jun 23, 2026

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Lakeside Hotel Deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

Lakeside MI

10/10 Exceptional! (144 reviews)

"Absolute paradise! The grounds are gorgeous with all of the plants and options for seating. Inside was cozy with everything we needed. We had dinner every evening in the screened in porch overlooking more gardens. Delightful!"

Reviewed on Jun 17, 2026

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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More

Lakeside MI

9.4/10 Exceptional! (68 reviews)

"Great place to stay - especially for a large family or friend group. Steps from the beach. Outstanding communication from property owner."

Reviewed on Jun 16, 2026

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Four Winds Casino Resort – New Buffalo

11111 Wilson Road New Buffalo MI

Fully refundable

CA $164

CA $191 total

Jun 29 - Jun 30

includes taxes & fees

9.4/10 Exceptional! (1,941 reviews)

"Excellent for the price. Nice staff. Clean areas. Only one place for breakfast"

Reviewed on Jun 23, 2026

See all 1,898 properties in Lakeside

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.