Title: South Side Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $1,462 Expedia.ca

[South Side Travel Guide](https://expedia.ca/South-Haven-South-Side.dx948692480694632448)[Hotels in South Side](https://expedia.ca/South-Side-Hotels.d948692480694632448.Travel-Guide-Hotels)[Flights to South Haven](https://expedia.ca/Cheap-Flights-To-South-Haven.d6757.Travel-Guide-Flights)[South Side Car Rentals](https://expedia.ca/Car-Rentals-In-South-Side.d948692480694632448.Car-Rental-Guide)

![](https://images.trvl-media.com/place/948692480694632448/eff6f1fd-b093-47fc-8056-7e84a958f44b.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# South Side Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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## Top Holiday Package Deals in South Side

Price found within the past 48 hours. Click for updated prices.

![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Level Chicago - River North

Downtown Chicago

CA $1,462

per person

May 10 - May 17

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (766 reviews)

Clean room and spacious.

Reviewed on Feb 18, 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 $1,492

per person

May 10 - May 17

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (2,790 reviews)

Great staff, clean rooms. Great location

Reviewed on Feb 21, 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 $1,494

per person

May 10 - May 17

found 21 hours 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

![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/f26e0a61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Wade

Downtown Chicago

CA $1,486

per person

May 10 - May 17

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

8.4/10 Very Good! (1,444 reviews)

We had a really good stay. The hotel is in a great location. We got a lakeview room, and it was right in front of the lake by Navy Pier. The view was beautiful. We had a king-size bed, and it was very comfortable. Check-in and check-out were very quick and easy. That made everything smooth from start to finish. The bathroom was clean and nice. The food and drinks were also very good. The only downside was that our room was close to the elevator, so it was a little noisy. You could hear it going up and down. There were also people smoking weed, and the smell would come in sometimes, which we did not like. But overall, it was a good stay. It was very close to Navy Pier, which was perfect since most of our plans were there.

Reviewed on Feb 22, 2026

![Stay One Chicago](https://images.trvl-media.com/lodging/113000000/112870000/112868000/112867973/0bd05cf3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Stay One Chicago

Downtown Chicago

CA $2,768

per person

May 10 - May 17

found 21 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

No reviews

The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel". So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into. Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I). The app never worked, and we finally got physical key cards from the guy working for the building. There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced. I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.

Reviewed on Feb 10, 2026

## Where to stay in South Side

Find the best South Side areas and neighborhoods for the activities you enjoy most. [Learn more about South Side](https://expedia.ca/South-Haven-South-Side.dx948692480694632448)

![Scenic fall foliage along Black river in Michigan upper peninsula](https://images.trvl-media.com/place/948676562717446144/05c47f5a-33de-47bf-b399-8c71fdc8ba91.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### North Side

1 out of top 10 points of interest in this area

 While visiting North Side, you might make a stop by sights like Michigan Maritime Museum and North Beach. 

[Find hotel + flight trips in North Side](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=North%20Side&DestID=948676562717446144&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![South Haven Pier has a nice beach. It’s busy during summer but it’s peaceful after the sunset.](https://images.trvl-media.com/place/6757/d29d2982-974b-4933-a4d6-7183e6ede273.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown

2 out of top 10 points of interest in this area

 If you're spending some time in Downtown, Warner Vineyards and Southside Municipal Marina are top sights worth seeing. 

[Find hotel + flight trips in Downtown](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown&DestID=948677654383628288&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Sunset on Port Camargue](https://images.trvl-media.com/place/553248635976479990/42a5025f-d6c4-4167-b919-adf371cf987e.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Miami Park

 While Miami Park isn't home to many top sights, Kal Haven Trail and North Beach are some notable places to visit nearby. 

[Find hotel + flight trips in Miami Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Miami%20Park&DestID=553248635976479990&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![South Haven Michigan - Lighthouse](https://images.trvl-media.com/place/553248635976480165/1e3091eb-8669-44a7-bd47-20127f4436ff.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Mt. Pleasant

 When in Mt. Pleasant, you can plan a visit to Kal Haven Trail and Michigan Maritime Museum, some noteworthy sights in the nearby area. 

[Find hotel + flight trips in Mt. Pleasant](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Mt.%20Pleasant&DestID=553248635976480165&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Lake Michigan - South Haven](https://images.trvl-media.com/place/553248635976479758/454be79f-09f3-4915-b96e-3e8ff0d76e24.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### West Wing Estates

 While West Wing Estates isn't home to many top sights, Kal Haven Trail and Michigan Maritime Museum are some notable places to visit nearby. 

[Find hotel + flight trips in West Wing Estates](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=West%20Wing%20Estates&DestID=553248635976479758&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## South Side Hotel Deals

![Overlook South Haven Harbor steps from South Beach and Downtown](https://images.trvl-media.com/lodging/35000000/34020000/34010200/34010105/f01958bd_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Overlook South Haven Harbor steps from South Beach and Downtown

 South Haven MI

10/10 Exceptional! (189 reviews)

We love South Haven in October and this trip did not disappoint! The location and charm of Crimson Sun was just what we were looking for.

Reviewed on Oct 21, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=34010105&PinnedHotelID=34010105&HadPinnedHotel=true&regionId=948692480694632448)

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=34010105&PinnedHotelID=34010105&HadPinnedHotel=true&regionId=948692480694632448)

![Baymont by Wyndham South Haven](https://images.trvl-media.com/lodging/1000000/120000/118600/118533/1acdeb2c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Baymont by Wyndham South Haven

1555 Phoenix Rd South Haven MI

Fully refundableReserve now, pay when you stay

CA $93

CA $103 total

Mar 1 - Mar 2

includes taxes & fees

7.6/10 Good! (1,000 reviews)

Very clean room and friendly staff!

Reviewed on Feb 15, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=118533&PinnedHotelID=118533&HadPinnedHotel=true&regionId=948692480694632448)

![Starlite Resort](https://images.trvl-media.com/lodging/12000000/11830000/11829000/11828943/28c0d503_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Starlite Resort

3353 Blue Star Highway Saugatuck MI

Fully refundableReserve now, pay when you stay

CA $132

CA $146 total

Feb 23 - Feb 24

includes taxes & fees

9.4/10 Exceptional! (813 reviews)

Everything was very clean, gentleman at the front desk was super friendly. We would definitely stay again!

Reviewed on Feb 8, 2026

[](https://expedia.ca/Hotel-Search?startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&selected=11828943&PinnedHotelID=11828943&HadPinnedHotel=true&regionId=948692480694632448)

[See all 2,010 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=23%2F02%2F2026&endDate=24%2F02%2F2026&regionId=948692480694632448)

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)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.