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

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,101, price is now CA $778 per person
CA $778
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good: Staff was great Location Comfortable bed The bad: Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$. Water pressure and heat of water terrible. TV didn't work very well Not much in room - small, no fridge, no microwave I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.

Reviewed on Jul 11, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $1,693, price is now CA $1,216 per person
CA $1,216
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on Jul 8, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,912, price is now CA $1,393 per person
CA $1,393
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Perfect location Perfect view excellent staff fun time had by wife for her birthday great little getaway thanks

Reviewed on Jul 11, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $3,029, price is now CA $2,213 per person
CA $2,213
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on Jul 9, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was CA $1,375, price is now CA $1,034 per person
CA $1,034
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (128 reviews)
Very nice rooms and excellent service. Our stay could not have been better!

Reviewed on Jul 11, 2026

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Lakeside Hotel Deals

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

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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Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location
Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

Lakeside MI
9/10 Wonderful! (51 reviews)
"We truly enjoyed our stay over the holiday weekend. We were a group of a adults so it was lovely that rooms gave us our own personal space but the large common area was wonderful when we all wanted to be together. Private beach access was great and the short walk was even better. We’d happily stay ..."

Reviewed on Jul 10, 2026

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Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!
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 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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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
See all 1,903 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
Beach Vacations
Family Vacations
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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.
See properties

Frequently asked questions

How much does a Lakeside vacation package cost?
You'll find cheap prices from CA $778 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.

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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.