Title:  South Side Vacation Packages & Trips 2025 from CA $629 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?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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### 

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## Top Holiday Package Deals in South Side

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 $725

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (1,011 reviews)

Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel

Reviewed on Oct 20, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rztsOHXyn6y_dAK5WW_50dHgpRELcg5HcZeh-WHPTP37P)

![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 $971

per person

Dec 12 - Dec 19

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,110 reviews)

Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly.

Reviewed on Oct 16, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=qgNx3gK80nWwTZhFUtG94B4y9nNG9EwM1y1arGXZ9VG9Ijqf-H9bL3O-oTLxb-zz)

![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Orrington / Evanston

Downtown Evanston

CA $739

per person

Dec 6 - Dec 13

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Chicago (ORD)

7.6/10 Good! (1,003 reviews)

The location of the Orrington is excellent but the star of the Orrington is delfinitely its staff. They were friendly, helpful and handled busy and problem situations with grace and solutions. Gotta love the midwest!

Reviewed on Oct 10, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-06/2025-12-13/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=3N3YfoFxJicbUeztIgTC6o3lH0hwX-tYPZOkEkfIomUuhnf5kail5j0pFUDbHKtM)

![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 $978

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9/10 Wonderful! (367 reviews)

We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue. However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).

Reviewed on Oct 22, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzhm0AWal_ZkRkIcRhPqrbTB3e7H7LB6K0J6TPjZCp-6w)

![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 $811

per person

Jan 17 - Jan 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Chicago (ORD)

9.2/10 Wonderful! (303 reviews)

Food price was high but everything was fine

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2026-01-17/2026-01-20/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=hEcxEAl0cQr8TKY7Kq7rzhm0AWal_ZkRkIcRhPqrbTBVQSzqnh27zy71H5yxiZYW)

## 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)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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)

![Default Image](https://mediaim.expedia.com/destination/1/7c8c7298efa9bd8cff0a7d87d2bb447b.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown

2 out of top 10 points of interest in this area

Downtown might not have many top sights, but Michigan Maritime Museum and Kal Haven Trail are two attractions nearby that you can check out.

[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)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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 Michigan Maritime Museum 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)

![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.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

![New build in 2021!  Short Walk To Beach & Downtown, Includes Hot Tub](https://images.trvl-media.com/lodging/67000000/66170000/66160600/66160528/a5be66f5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

New build in 2021! Short Walk To Beach & Downtown, Includes Hot Tub

South Haven

10/10 Exceptional! (34 reviews)

House was clean and close to beach and downtown. Enjoyed it very much!

Reviewed on Sep 11, 2025

[Get rates](https://expedia.ca/Hotel-Search?startDate=07%2F11%2F2025&endDate=08%2F11%2F2025&selected=66160528&PinnedHotelID=66160528&HadPinnedHotel=true&regionId=948692480694632448)

[](https://expedia.ca/Hotel-Search?startDate=07%2F11%2F2025&endDate=08%2F11%2F2025&selected=66160528&PinnedHotelID=66160528&HadPinnedHotel=true&regionId=948692480694632448)

![Old Harbor Inn](https://images.trvl-media.com/lodging/42000000/41980000/41975100/41975008/a8b9eb66_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Old Harbor Inn

515 Williams Street, South Haven, MI

Fully refundableReserve now, pay when you stay

CA $179

CA $199 total

Oct 26 - Oct 27

includes taxes & fees

9.4/10 Exceptional! (657 reviews)

Great location to everything in South Haven. Very nice staff and clean and comfortable room! Would definitely recommend

Reviewed on Oct 14, 2025

[](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=41975008&PinnedHotelID=41975008&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, I-196 Exit 20, South Haven, MI

Fully refundableReserve now, pay when you stay

CA $89

CA $99 total

Nov 2 - Nov 3

includes taxes & fees

7.6/10 Good! (1,020 reviews)

No meat offered in the breakfast options.

Reviewed on Oct 17, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=118533&PinnedHotelID=118533&HadPinnedHotel=true&regionId=948692480694632448)

[See all 2,005 properties in South Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025&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.