Lakeside Vacation Packages

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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

The Royal Sonesta Chicago River North

4.5 out of 5
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

Trump International Hotel & Tower Chicago

5 out of 5
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

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
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

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
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

Park Hyatt Chicago

5 out of 5
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

Ready to book your vacation to Lakeside?

 

Choose your dates

Lakeside Hotel Deals

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

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

Get rates
1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
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

Four Winds Casino Resort – New Buffalo
Quality Inn Near Interstate I94

Quality Inn Near Interstate I94

2.5 out of 5
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

Quality Inn Near Interstate I94
See all 1,821 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Lakeside vacation package cost?
You'll find cheap prices from CA $639 on Expedia for your Lakeside getaway. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Lakeside costs.
What are the cheapest months to go to Lakeside?
Plan your trip for the off-peak season and you're likely to get cheap Lakeside vacation packages. Bear in mind that public holidays and major local events can impact prices, so do a little research before booking.
How many days is enough for Lakeside?
Lakeside vacations come in many shapes and sizes, but to get a true feel for this destination, we think 3 days is a good ballpark. In this timeframe, you can fit in major attractions like Warren Dunes State Park Beach and New Buffalo Public Beach and track down some underrated spots. Don't miss out on neighbourhoods such as Gordon Beach and Harbert either. If you're smart with your time, you may even be able to take a day trip outside of Lakeside too.
How to find the best Lakeside package deals?
Use Expedia's filter tool to find some tempting Lakeside package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Lakeside package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Lakeside vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Lakeside?
If you have your Lakeside travel dates confirmed, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Lakeside?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Lakeside.
  2. Set a budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Lakeside. Then, choose a property that suits your budget, whether that's a wallet-friendly option or a high-end retreat.
  3. Work out your trip length: Consider how much time you want to spend exploring Lakeside. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Lakeside 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.