Title: Lakeside Vacation Packages & Trips 2026 from CA $979 | 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.

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $979

per person

Apr 1 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (1,001 reviews)

Perfect location, comfortable and clean room

Reviewed on Jan 5, 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 $1,036

per person

Apr 1 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Great breakfast, Clean room, enjoyed the stay

Reviewed on Jan 9, 2026

![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 $1,524

per person

Feb 13 - Feb 18

found 24 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.4/10 Exceptional! (1,773 reviews)

Stayed in a river view room over NYE and had a great view of the fireworks show on the river! The staff was superb and went above and beyond for us. Extremely kind and knowledgeable. Cannot wait to stay again!

Reviewed on Jan 3, 2026

![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 $1,055

per person

Apr 1 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9/10 Wonderful! (380 reviews)

Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Peninsula Chicago

Downtown Chicago

CA $2,135

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Chicago (ORD)

9.8/10 Exceptional! (1,003 reviews)

Upon check-in, it was magical! The doormen were amazing, the 'go as often as you'd like' Santa's candy shop, overall hotel decorations and the professionalism of the staff will blow you away!!! This hotel is next level up and puts the Ritz Carlton down a notch, for sure. Our room was truly magnificent and I wish we could have stayed longer!

Reviewed on Jan 6, 2026

## 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

9.8/10 Exceptional! (113 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=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=34747841&PinnedHotelID=34747841&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%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=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=66850572&PinnedHotelID=66850572&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%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! (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=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true&regionId=68053)

[](https://expedia.ca/Hotel-Search?startDate=24%2F01%2F2026&endDate=25%2F01%2F2026&selected=27128869&PinnedHotelID=27128869&HadPinnedHotel=true&regionId=68053)

[See all 1,859 properties in Lakeside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F01%2F2026&endDate=12%2F01%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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