
Lakeside Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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 Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $1,018, price is now CA $639 per person
CA $639
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Great Staff, Beautiful Hotel!
Reviewed on Aug. 22, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $3,441, price is now CA $1,974 per person
CA $1,974
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug. 19, 2025

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,775, price is now CA $1,041 per person
CA $1,041
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
Staff were excellent, I needed to mail some parcels for a business event which they held for over a week (arrived earlier than expected!) breakfast was also excellent. Rooms were noisy, not from outside but from the other rooms. Walls must be thin and could hear conversation and the TV from both sides.
Reviewed on Aug. 20, 2025

Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Price was CA $2,444, price is now CA $1,439 per person
CA $1,439
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug. 21, 2025

Park Hyatt Chicago
Downtown Chicago
Price was CA $3,954, price is now CA $2,330 per person
CA $2,330
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!
Reviewed on Aug. 10, 2025
Lakeside Hotel Deals

1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Lakeside
9.2/10 Wonderful! (52 reviews)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."
Reviewed on Jul. 30, 2025

Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is CA $149 per night from Sep 3 to Sep 4
CA $149
CA $173 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (1,467 reviews)
"Great view of the woods and the deer, And the sky view was nice, not many city lights"
Reviewed on Aug. 19, 2025

Quality Inn Near Interstate I94
18830 Laporte Rd, New Buffalo, MI
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Sep 1 to Sep 2
CA $119
CA $126 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
First time in New Buffalo
"Desk staff helpful. Bathroom had some mold on wall near tub otherwise room was fine. Breakfast was good"
Reviewed on Aug. 20, 2025
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.