Lakeside Vacations from $646
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The Latest Lakeside Vacation Packages
- Hotel Felix River North/Magnificent Mile
Sep 23 - Sep 28Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago5 nights4.0 star property8.2/10 - Very Good (2,841 reviews)"decent property - definitely shows better in photos. that was probably my biggest let-down. also, only staying one night, the room cleaner came into our room at 8 am despite check out time not being until noon. my kid was still asleep and I was in the shower. front desk service level definitely elevated the rating."Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago - River North
Sep 23 - Sep 28Level Chicago - River North + Flight
Downtown Chicago5 nights4.0 star property9.2/10 - Wonderful (1,035 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Sep 25 - Sep 29Level Chicago – Old Town + Flight
Downtown Chicago4 nights4.0 star property9.0/10 - Wonderful (501 reviews)"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."Reviewed July 14, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Sable at Navy Pier Chicago, Curio Collection by Hilton
Sep 27 - Oct 1Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (2,590 reviews)Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop MDW - ATL • Nonstop - Urban Chicago Oasis
Sep 6 - Sep 9Urban Chicago Oasis + Flight
Lakeview3 nights2.0 star propertyRoundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop MDW - ATL • Nonstop
Lakeside Hotel Deals
Hampton Inn & Suites Michigan City
Hampton Inn & Suites Michigan City
Home2 Suites by Hilton Michigan City
Home2 Suites by Hilton Michigan City
Fairfield Inn & Suites by Marriott New Buffalo
Fairfield Inn & Suites by Marriott New Buffalo
Holiday Inn Express & Suites La Porte by IHG
Holiday Inn Express & Suites La Porte by IHG
Four Winds Casino Resort – New Buffalo
Four Winds Casino Resort – New Buffalo
Frequently Asked Questions
How much does a Lakeside vacation package cost?
Offering great value package deals from $646 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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Things to do near Lakeside
Lakeside, Michigan, is perfect for outdoor and romantic getaways, offering a variety of activities. Visitors can enjoy lakefront vacations, river adventures, and a range of fun outdoor activities. The area features a recreational space, playground, and campground, making it an ideal spot for family and nature lovers alike. Whether you're seeking relaxation by the water or an adventurous day, Lakeside has something for everyone.
Shopping
Lakeside offers charming shopping experiences with local favorites like Round Barn Winery and Founders Wine Cellar, both 12 miles away. If you're up for a drive, check out Lighthouse Place Premium Outlets, 15 miles away, where you can enjoy a variety of shops and family-friendly entertainment.
Recreation
Explore Weko Park, just 8 miles from Lakeside, where you can unwind amidst nature and enjoy tranquil walking trails. Visit Galien River County Park, only 4 miles away, for serene landscapes and relaxation opportunities. Don’t miss The Acorn theater, 4 miles from Lakeside, offering cultural entertainment for the family.
Adventure
At Captain Mike's Fun Park, located 7 miles from Lakeside, enjoy thrilling arcade games and family-friendly activities. Experience the excitement of motor racing at Red Bud Track-N-Trail, situated 16 miles away. For water fun, visit Surfari Joe's Indoor Wilderness Water Park, 31 miles from Lakeside, featuring thrilling slides and attractions.
Nightlife
Experience the vibrant nightlife in Lakeside by visiting Round Barn Union Pier Tasting Room, only a mile away, offering a romantic vibe. For a unique experience, check out Round Barn Baroda Tasting Room & Estate, 12 miles away, or Free Run Cellars, 14 miles away, both perfect for winding down with drinks.
Find the best attractions near Lakeside
Lakeside, Michigan, is the perfect destination for outdoor enthusiasts and couples seeking a romantic getaway. Surrounded by beautiful beaches and stunning lake views, visitors can explore nearby state parks and indulge in leisure activities at lake resorts. Whether you're looking for scenic spots or relaxing lakeside experiences, Lakeside offers a delightful blend of natural beauty and recreational opportunities for every traveler.
- Warren Dunes State Park: Experience the thrill of adventure at Warren Dunes State Park, just 6 miles from Lakeside. Enjoy hiking trails that lead to stunning views of Lake Michigan, or spend the day relaxing on the sandy shores. The park is perfect for picnicking, birdwatching, and various outdoor activities amidst beautiful natural scenery.
- New Buffalo Public Beach: Located only 5 miles away, New Buffalo Public Beach offers a perfect getaway with its inviting sandy shores and vibrant beach vibes. Relax under the sun, swim in the clear waters, or stroll along the picturesque shoreline—this beach is a favorite spot for both locals and visitors.
- Local: Just 5 miles from Lakeside, this local attraction showcases the unique culture and charm of the area. Explore shops, dine at delightful restaurants, and immerse yourself in the community's lively atmosphere.
Best time to go to Lakeside
The best time to visit Lakeside is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.
Tips to save on your trip to Lakeside
- Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Lakeside.
- Consider traveling during the off-peak season (typically March and December to January) for more affordable package holidays to Lakeside.
- Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
- Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.