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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
CA $1,135
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,960 reviews)
I loved the room, the cleanliness, the ambiance, but I just think you should offer breakfast. Otherwise the place is great!
Reviewed on Aug 25, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,360
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
The views are nice. The room is more simple. The bathroom needs to be upgraded. Definitely just 3.5-4*. The late night snack area is a nice feature though.
Reviewed on Aug 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,313
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
Nice place and location, especially if you have a good room. It's expensive but you get good experiance
Reviewed on Aug 26, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $1,914
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Amazing hotel in excellent location. We loved our stay and hope to return for another trip to Chicago.
Reviewed on Aug 23, 2026
Ready to book your vacation to Lakeside?
Lakeside Hotel Deals
Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Lakeside MI
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
Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundable
CA $148
CA $172 total
Sep 14 - Sep 15
includes taxes & fees
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.
Stay near popular Lakeside attractions
Burnison Galleries
You can spend time studying the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.
Eleanor O'Connor Wilson Woods Preserve
You can take time to visit Eleanor O'Connor Wilson Woods Preserve during your travels to Lakeside. Stroll along the lakeside or discover the area's sunsets.
Frequently asked questions
How much does a Lakeside vacation package cost?
You'll find cheap prices from CA $1,135 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?
- 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.
- 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.
- 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.
- 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.
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- Lovely recently Built NB Home
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- Two separate updated secluded cottages for one price. near beach & restaurants
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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.
