Lakeside Holidays from £966

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Your Lakeside Holiday

With a Lakeside holiday 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 holiday to Lakeside today.

Top Lakeside Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
Highland Hills
per person
4 Nov - 7 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (2,161 reviews)
The bed was comfortable.

Reviewed on 11 Aug 2025

Chez Hotel Arlington Heights

Chez Hotel Arlington Heights

4 out of 5
per person
4 Nov - 7 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (396 reviews)
Very nice hotel. New, very clean, staff did offer new roof bar and restaurant that recently opened. No ironing board and iron but that wasn’t a big deal.

Reviewed on 7 Aug 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
4 Nov - 7 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,270 reviews)
i’ve stayed here a few times and love it. it’s my go to, i highly recommend this place!

Reviewed on 11 Aug 2025

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

2.5 out of 5
Bedford Park
per person
4 Nov - 7 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,115 reviews)
Bathtub chipped, slippery and to small. Bathroom could use a facelift. Bed was great! Refrigerator in our room did not work. Staff offered to replace it but we didn't need it.

Reviewed on 3 Aug 2025

Ohio House Motel

Ohio House Motel

3 out of 5
Downtown Chicago
per person
4 Nov - 7 Nov
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (1,012 reviews)
Super convenient and nice area. Straight walk to Wrigley Field (4 miles but we enjoyed the walks). Very affordable and has a great staff.

Reviewed on 9 Aug 2025

Lakeside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
South Bend Intl. Airport (SBN)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Warren Dunes State Park, Warren Dunes State Park Beach and New Buffalo Public Beach

Top hotels in Lakeside

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
9.2/10 Wonderful! (52 reviews)
"Great rental for multiple families. It was terrific having a pool and the beach was wonderful and close by."

Reviewed on 30 Jul 2025

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1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More
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
The price is £117 per night from 18 Aug to 19 Aug
£117
18 Aug - 19 Aug
includes taxes & fees
8.2/10 Very Good! (1,659 reviews)
"Great"

Reviewed on 11 Aug 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 refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,465 reviews)
"Steak house staff was excellent and food was good"

Reviewed on 10 Aug 2025

Get rates
Four Winds Casino Resort – New Buffalo
See all 1,822 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Burnison Galleries

You can spend an afternoon browsing the exhibits at Burnison Galleries in Lakeside. Stroll along the beautiful beaches or visit the casinos in this romantic area.

Burnison Galleries

Frequently asked questions

Why should I book my Lakeside holiday with Expedia?
Choose Expedia to plan your next adventure easily and all in one place. Our top tip for bagging the best deal on a Lakeside retreat? Bundle your flights, accommodation and/or hire car into a package holiday. Then add some fun tours and activities. Most bookings also include flexible cancellation policies, so there's no need to panic if you have to switch up your itinerary. Round-the-clock assistance with cancelling and amending your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Lakeside?
Lakeside draws the crowds in May, June and July. If you want a more relaxed holiday, head there in November, December and January. With average daytime temperatures of -3ºC, January is the coolest month in Lakeside. The warmest month is July, when you can experience averages of 22ºC throughout the day. Whatever the weather conditions, you'll discover loads to keep you entertained here.
What is the top hotel for my holiday in Lakeside?
Offering many of home's creature comforts, Comfort Suites Stevensville - St. Joseph will make an ideal base for your Lakeside holiday.
How do I get a cheap holiday to Lakeside?
Creating your own Lakeside holiday with Expedia is a simple way to save. We have over 400 air carriers and 321,000 hotel options throughout the world. With such a broad range to pick from, you'll have no difficulty creating your dream adventure. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Lakeside holiday?
Make sure your next holiday in Lakeside is a memorable one by taking in its major attractions. Four Winds Casino New Buffalo, New Buffalo Public Beach, Warren Dunes State Park Beach and Michiana Beach are just some of the things we recommend seeing while you're in this city.
What is the best area to stay in when on holiday in Lakeside?
If you plan to check out Burnison Galleries, save yourself the hassle of commuting and find somewhere to stay close by. It's one of the most popular attractions in Lakeside.
Do I need a visa for my Lakeside holiday?
Research the latest rules on official government websites. Your nationality and whether you're visiting for study, leisure or business will determine if you'll require a visa for Lakeside. Familiarise yourself with the application process, including the required documentation, fees and turnaround times. Finalise your application well in advance to allow enough time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Lakeside holiday?
Though everyone's style is different, it can be helpful to have a few guidelines for what kind of clothes to wear on your holiday in Lakeside. We recommend browsing style blogs before you head off for inspiration on local fashion trends. Daytime temperatures during January, Lakeside's coolest month, average around -3ºC. July marks this destination's warmest month when the average temperature reaches 22ºC. Our suggestion? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Lakeside holiday include?
It depends on what sort of trip you're planning. Lakeside travel deals can include hotels, car hires and flights. You can mix and match to create the package that suits your budget and style. You can also add on activities and experiences after you've booked to score even bigger discounts. Explore a large selection of property types and pick one that suits the size of your group. The most in-demand rentals here are private holiday homes and cottages. With Expedia, it's easy to design your Lakeside escape however you like.
Does Expedia offer Book Now, Pay Later Lakeside holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you easily pay for your trip in instalments. Simply click on the payment plan that suits you best during checkout and take the stress out of budgeting for your trip. Make sure you bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: If paying across multiple transactions sounds right for you, Klarna offers just that! Paying in convenient monthly instalments will make your getaway dreams come true.
  • No-deposit holidays: Hitting the "book now" button is easier with this plan. With no deposit required for your getaway, you can Book Now, Pay Later and start working on your travel itinerary.

Can I choose my airline with a Lakeside Expedia holiday?
Yes, you're in control. Expedia has access to more than 400 airlines around the world, so you can tailor your Lakeside holiday according to your travel preferences.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.