Title: Lakeside Vacation Packages & Trips 2025/2026 from CA $514 | Expedia.ca [Hotels in Lakeside](https://expedia.ca/Lakeside-Hotels.d68053.Travel-Guide-Hotels)[Vacation Rentals in Lakeside](https://expedia.ca/Lakeside-Vacation-Rentals.d68053.Travel-Guide-VacationRentals)[Lakeside Car Rentals](https://expedia.ca/Car-Rentals-In-Lakeside.d68053.Car-Rental-Guide) ![](https://images.trvl-media.com/place/68053/5c33d279-2fa8-44b8-b98f-31d29f329548.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Lakeside Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### 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](https://www.expedia.ca/Four-Winds-Casino-New-Buffalo-New-Buffalo.d6175953.Vacation-Attraction), [New Buffalo Public Beach](https://www.expedia.ca/New-Buffalo-Public-Beach-Michigan.d553248621532658899.Vacation-Attraction) and [Warren Dunes State Park Beach](https://www.expedia.ca/Warren-Dunes-State-Park-Beach-Michigan.d690453123469586432.Vacation-Attraction), 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. ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $514 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 18.4/10 Exceptional! (317 reviews) I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location. Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-21/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=9A9SWV9x1H9ONn54uEbZ6r9lpfmTIvP21zjHfTInUHf4D75t3QR0LJJJo34jDegu) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $850 per person Dec 27 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 17.6/10 Exceptional! (1,075 reviews) Just slept there overnight. Reviewed on Nov 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=IKzTYHpgox_et4ooTuz3QW4aVRsDz14_8TzgBMNpshXivP9gsqBxpmvniyHkcNQA) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $722 per person Feb 17 - Feb 21 found 13 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 18/10 Exceptional! (380 reviews) Property was clean, centrally located with wonderful staff. Will definitely stay again. Reviewed on Nov 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-21/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=3xRRZ_VgqZ-a3jf-8SLVTG6oWACxL_BLszGd91XZl8LzZ5wraAp1cVsMAsVRdBJK) ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $583 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 18.8/10 Exceptional! (1,130 reviews) Clean and great service. Reviewed on Nov 21, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-21/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=VLo3IfT45O7H9uJGG3h_C3Om4Y53DFzQtOy84rn8pDzTzU0cELvBR1Lf_KgqX0T1) ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,032 per person Feb 17 - Feb 21 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 18.8/10 Exceptional! (1,773 reviews) Great stay. Excellent location. Reviewed on Nov 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-17/2026-02-21/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=VLo3IfT45O7H9uJGG3h_C_bTH4Zg-ZR7CH_ByVcoklXsDnhGRSYR4oIJbPX88AWH) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_68053) ## Ready to book your vacation to Lakeside? Choose your dates ## Lakeside Hotel Deals ![1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More](https://images.trvl-media.com/lodging/28000000/27130000/27128900/27128869/1d07d01f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 1 or 2 Fun Cottages Sleep 2-10-20 People. Pool & Hot Tub. Steps to Beach + More Lakeside MI 9.2/10 Wonderful! (55 reviews) Great property. Just as advertised. Hope to come back soon Reviewed on Sep 26, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F12%2F2025&endDate=09%2F12%2F2025&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true®ionId=68053) [](https://expedia.ca/Hotel-Search?startDate=08%2F12%2F2025&endDate=09%2F12%2F2025&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true®ionId=68053) ![Blue Chip Casino Hotel and Spa](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Blue Chip Casino Hotel and Spa 777 Blue Chip Drive Michigan City IN Fully refundableReserve now, pay when you stay CA $101 CA $133 total Dec 1 - Dec 2 includes taxes & fees 8.2/10 Very Good! (1,827 reviews) property was nice and clean and the employees were polite and professional. Would stay again Reviewed on Nov 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=01%2F12%2F2025&endDate=02%2F12%2F2025&selected=2991209&PinnedHotelID=2991209&HadPinnedHotel=true®ionId=68053) ![Four Winds Casino Resort – New Buffalo](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Four Winds Casino Resort – New Buffalo 11111 Wilson Road New Buffalo MI Fully refundableReserve now, pay when you stay CA $108 CA $125 total Nov 25 - Nov 26 includes taxes & fees 9.2/10 Wonderful! (1,614 reviews) Room was very clean, staff was nice & friendly. Overall great stay! Reviewed on Nov 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F11%2F2025&endDate=26%2F11%2F2025&selected=13278629&PinnedHotelID=13278629&HadPinnedHotel=true®ionId=68053) [See all 1,860 properties in Lakeside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F11%2F2025&endDate=26%2F11%2F2025®ionId=68053) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - 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[Harbert Vacations](https://www.expedia.ca/Harbert.d553248635974530614.Destination-Travel-Guides) - [Hastings Country Club](https://www.expedia.ca/Hastings-Country-Club-Hastings.d6274502.Vacation-Attraction) - [Holland State Park](https://www.expedia.ca/Holland-State-Park-Holland.d6092325.Vacation-Attraction) - [Holland Vacations](https://www.expedia.ca/Holland.d6059199.Destination-Travel-Guides) - [Kalamazoo Vacations](https://www.expedia.ca/Kalamazoo.d486.Destination-Travel-Guides) - [Lake allegan](https://www.expedia.ca/Lake-Allegan-Allegan.d553248621532659520.Vacation-Attraction) - [Marcellus Vacations](https://www.expedia.ca/Marcellus.d3000442306.Destination-Travel-Guides) - [Markin Glen County Park](https://www.expedia.ca/Markin-Glen-County-Park-Kalamazoo.d553248621532659578.Vacation-Attraction) - [Mt. Pisgah Dune Boardwalk](https://www.expedia.ca/Mt-Pisgah-Dune-Boardwalk-Ottawa-Beach.d553248621564732215.Vacation-Attraction) - [Oasis Hot Tub Gardens](https://www.expedia.ca/Oasis-Hot-Tub-Gardens-Kalamazoo.d553248621532659571.Vacation-Attraction) - [Oval Beach](https://www.expedia.ca/Oval-Beach-Saugatuck.d553248621532659508.Vacation-Attraction) - [Saugatuck Dunes State Park](https://www.expedia.ca/Saugatuck-Dunes-State-Park-Holland.d6092455.Vacation-Attraction) - [Saugatuck Vacations](https://www.expedia.ca/Saugatuck.d155409.Destination-Travel-Guides) - [Southwest Michigan Vacations](https://www.expedia.ca/Southwest-Michigan.d6059187.Destination-Travel-Guides) - [Surfari Joe's Indoor Wilderness Water Park](https://www.expedia.ca/Surfari-Joes-Indoor-Wilderness-Water-Park-Watervliet.d553248621532658958.Vacation-Attraction) - [Tri-Cities Historical Museum](https://www.expedia.ca/Tri-Cities-Historical-Museum-Grand-Haven.d553248621532659541.Vacation-Attraction) - [Tyden Park](https://www.expedia.ca/Tyden-Park-Hastings.d6274495.Vacation-Attraction) - [Visit Union Pier](https://www.expedia.ca/Union-Pier.dx168440) - [Van Buren State Park](https://www.expedia.ca/Van-Buren-State-Park-Michigan.d553248621532659484.Vacation-Attraction) - [Vander Veen's Dutch Store](https://www.expedia.ca/Vander-Veens-Dutch-Store-Grand-Rapids.d553248621532659713.Vacation-Attraction) - [Wade's Bayou Memorial Park](https://www.expedia.ca/Wades-Bayou-Memorial-Park-Douglas.d553248635544159434.Vacation-Attraction) - [Windmill Island](https://www.expedia.ca/Windmill-Island-Downtown-Holland.d6092445.Vacation-Attraction) ### Cars - [Addcar rental Rental Cars in Harbour Country](https://www.expedia.ca/AddCar-Rental-Car-Rentals-In-Harbour-Country.d553248635975749480-c1002.Car-Rental-Guide-Suppliers) - [Alamo Rent A Car Rental Cars in Harbour Country](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Harbour-Country.d553248635975749480-c6.Car-Rental-Guide-Suppliers) - [Auto Rent Rental Cars in Harbour Country](https://www.expedia.ca/Auto-Rent-Car-Rentals-In-Harbour-Country.d553248635975749480-c1006.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Harbour Country](https://www.expedia.ca/Avis-Car-Rentals-In-Harbour-Country.d553248635975749480-c41.Car-Rental-Guide-Suppliers) - [Bidvest Rental Cars in Harbour Country](https://www.expedia.ca/Bidvest-Car-Rentals-In-Harbour-Country.d553248635975749480-c1087.Car-Rental-Guide-Suppliers) - [Car rentals near Local](https://www.expedia.ca/Car-Rentals-In-Local.d553248621532658898.Car-Rental-Guide) - [Enterprise Rental Cars in Harbour Country](https://www.expedia.ca/Enterprise-Car-Rentals-In-Harbour-Country.d553248635975749480-c15.Car-Rental-Guide-Suppliers) - [Europcar Rental Cars in Harbour Country](https://www.expedia.ca/Europcar-Car-Rentals-In-Harbour-Country.d553248635975749480-c14.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Harbour Country](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Harbour-Country.d553248635975749480-c33.Car-Rental-Guide-Suppliers) - [Thai Cars Rental Cars in Harbour Country](https://www.expedia.ca/Thai-Cars-Car-Rentals-In-Harbour-Country.d553248635975749480-c1027.Car-Rental-Guide-Suppliers) - [Whiz Rental Cars in Harbour Country](https://www.expedia.ca/Whiz-Car-Rentals-In-Harbour-Country.d553248635975749480-c1117.Car-Rental-Guide-Suppliers) ### Vacation Rental - [Harbour Country Vacation Rentals](https://www.expedia.ca/Harbour-Country-Vacation-Rentals.d553248635975749480.Travel-Guide-VacationRentals) - [Sawyer Vacation Rentals](https://www.expedia.ca/Sawyer-Vacation-Rentals.d6048816.Travel-Guide-VacationRentals) - [Union Pier Vacation Rentals](https://www.expedia.ca/Union-Pier-Vacation-Rentals.d168440.Travel-Guide-VacationRentals) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)