Lakeside Vacations from $212

Book a Hotel + Flight or Car together to unlock savings

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.

The Latest Lakeside vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $361, price is now $212 per person
$212
per person
Nov 11 - Nov 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast are fresh. Shops are near by.

Reviewed on Oct 10, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $1,560, price is now $624 per person
$624
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,046 reviews)
One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done.

Reviewed on Oct 2, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Price was $455, price is now $225 per person
$225
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine

Reviewed on Oct 4, 2025

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Save 100% on your flight
Price was $559, price is now $318 per person
$318
per person
Dec 11 - Dec 16
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (MDW)
8.2/10 Very Good! (1,009 reviews)
Nothing to complain about. It’s an okay place.

Reviewed on Oct 10, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,001, price is now $576 per person
$576
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.

Reviewed on Oct 6, 2025

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Discover the most popular places to visit in Lakeside

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.

Burnison Galleries

Lakeside Hotel Deals

Blue Chip Casino Hotel and Spa

Blue Chip Casino Hotel and Spa

3.5 out of 5
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $130 total per night from Oct 12 to Oct 13
$130 total
Oct 12 - Oct 13
Total with taxes and fees
8.2/10 Very Good! (1,755 reviews)
"Clean place and easy to get to"

Reviewed on Oct 6, 2025

Blue Chip Casino Hotel and Spa
Four Winds Casino Resort – New Buffalo

Four Winds Casino Resort – New Buffalo

3.5 out of 5
11111 Wilson Road, New Buffalo, MI
Fully refundable
$120 nightly
The price is $126 total per night from Nov 3 to Nov 4
$126 total
Nov 3 - Nov 4
Total with taxes and fees
9.2/10 Wonderful! (1,538 reviews)
"Amazing experience all around"

Reviewed on Oct 7, 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
$77 nightly
The price is $81 total per night from Oct 19 to Oct 20
$81 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
Great Budget Hotel
"Clean rooms and hotel. And super helpful staff."

Reviewed on Oct 6, 2025

Quality Inn Near Interstate I94
See all 1,863 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.

Lakeside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
South Bend Intl. Airport (SBN)
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Warren Dunes State Park, Warren Dunes State Park Beach and Michiana Beach

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Frequently asked questions

How much does a Lakeside vacation package cost?
Offering great value package deals from $212 on Expedia, you'll be pleasantly surprised at how much a vacation to Lakeside costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Lakeside?
If you'd like to score a cheap Lakeside vacation package, consider planning a trip in November, December and January. You're likely to find better prices on flights and accommodations during these months — perfect for a budget-friendly break.
How many days is enough for Lakeside?
With a well-planned itinerary, you can easily hit the main Lakeside sights in a handful of days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Lakeside vacation for longer.
How to find the best Lakeside package deals?
Use Expedia's filters to find some great Lakeside package deals. When you start 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 escape for midweek, or browse for Lakeside package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Lakeside vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Lakeside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Lakeside?
Score amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Lakeside break.
Does Expedia offer Book Now, Pay Later Lakeside vacation packages?
Your Lakeside getaway should be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.