Lakeside Vacations from $314
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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.
The Latest Lakeside vacation packages
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,353 reviews)
We liked the view and the location. With our second visit here the front desk check-in gentleman was not as warm and friendly as other staff have been. We always have a great experience with the valet (they are helpful in finding transportation) and the luggage handlers were very accommodating. Our room was cleaned very well after the very first day.
Reviewed on Jul 3, 2025
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (1,785 reviews)
Stay was great
Stuff was fantastic
Area is great
One thing which bothered me - TV was turning on on it’s own during the night
Oh well
Reviewed on Jul 1, 2025
Hilton Chicago O'Hare Airport
O'Hare
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.
Reviewed on Jul 2, 2025
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.
Lakeside Hotel Deals
Blue Chip Casino Hotel and Spa
777 Blue Chip Drive, Michigan City, IN
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $157 total per night from Jul 7 to Jul 8
$157 total
Jul 7 - Jul 8
Total includes taxes and fees
8/10 Very Good! (1,571 reviews)
"The property was very clean and the staff was professional and nice"
Reviewed on Jun 30, 2025
Four Winds Casino Resort – New Buffalo
11111 Wilson Road, New Buffalo, MI
$164 nightly
The price is $173 total per night from Jul 31 to Aug 1
$173 total
Jul 31 - Aug 1
Total includes taxes and fees
9.2/10 Wonderful! (1,349 reviews)
"Event was within the property. Lots to do with music/band playing by the pool and close to Lake Michigan."
Reviewed on Jun 30, 2025
Baymont by Wyndham Michigan City
4128 South Franklin Street, Michigan City, IN
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Jul 6 to Jul 7
$90 total
Jul 6 - Jul 7
Total includes taxes and fees
5.6/10 (961 reviews)
Decent Hotel for the Price
"Overall, The Baymont is a decent choice if you’re looking for somewhere reasonably priced and convenient. It’s not a luxury experience by any means, but it’s functional and does the job for a short stay. There are certainly some areas that could be improved, but for the price, it’s not a bad ..."
Reviewed on Jul 2, 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.
Find the Best Lakeside Vacation Packages
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.