Title: Lakeside Vacation Packages & Trips 2026 from CA $718 | 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/a01c078f-b5b0-4003-8b21-5e2e24541060.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.

![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### La Banque Hotel

CA $718

per person

May 4 - May 8

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (447 reviews)

Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

CA $763

per person

Apr 3 - Apr 6

found 15 hours ago

Roundtrip flight included

Hamilton (YHM) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

St Add very friendly, clean and great breakfast

Reviewed on Feb 25, 2026

![Hotel Arista](https://images.trvl-media.com/lodging/3000000/2150000/2141800/2141763/43aaf412_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Arista

CA $785

per person

May 4 - May 8

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,003 reviews)

Room was great, staff service was also great !!

Reviewed on Feb 20, 2026

![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago Fulton Market

Downtown Chicago

CA $1,107

per person

May 17 - May 20

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (347 reviews)

Room smelled like food but overall very clean, very great service and staff both night and morning shift.

Reviewed on Feb 16, 2026

![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 $889

per person

Apr 9 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,130 reviews)

Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on Jan 31, 2026

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_68053)

## Ready to book your vacation to Lakeside?

Choose your dates

## Lakeside Hotel Deals

![Lakeside Grove Cottage -  Perfect Lakeside Village/Beach Location](https://images.trvl-media.com/lodging/35000000/34750000/34747900/34747841/f3db20d5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Lakeside Grove Cottage - Perfect Lakeside Village/Beach Location

 Lakeside MI

10/10 Exceptional! (138 reviews)

Great place. Beautiful home and perfect location to New Buffalo, Lakeside, and other places. The owner was very responsive and helpful. Strongly recommend this home.

Reviewed on Nov 9, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=34747841&PinnedHotelID=34747841&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=34747841&PinnedHotelID=34747841&HadPinnedHotel=true&regionId=68053)

![Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!](https://images.trvl-media.com/lodging/67000000/66860000/66850600/66850572/02846907_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Carrie's Cottage - Charming Duplex Style 3 Bedroom Cottage with Beach Access!

 Lakeside MI

9/10 Wonderful! (50 reviews)

Really liked the layout, the added privacy of the studio was great though it could use a microwave, table or desk and a place to put clothes. The beach is great and the kayaks are a great added bonus.

Reviewed on Sep 25, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=66850572&PinnedHotelID=66850572&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=66850572&PinnedHotelID=66850572&HadPinnedHotel=true&regionId=68053)

![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! (66 reviews)

Great property. Just as advertised. Hope to come back soon

Reviewed on Sep 26, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true&regionId=68053)

[See all 1,814 properties in Lakeside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&regionId=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)

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- [Harbour Country Vacation Rentals ](https://www.expedia.ca/Harbour-Country-Vacation-Rentals.d553248635975749480.Travel-Guide-VacationRentals)
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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.

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