Title: North Side Vacation Packages & Trips 2025 from CA $785 | Expedia.ca [North Side Travel Guide](https://expedia.ca/South-Haven-North-Side.dx948676562717446144)[Hotels in North Side](https://expedia.ca/North-Side-Hotels.d948676562717446144.Travel-Guide-Hotels)[Flights to South Haven](https://expedia.ca/Cheap-Flights-To-South-Haven.d6757.Travel-Guide-Flights)[North Side Car Rentals](https://expedia.ca/Car-Rentals-In-North-Side.d948676562717446144.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) # North Side 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 ## Top Holiday Package Deals in North Side Price found within the past 48 hours. Click for updated prices. ![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 $548 per person Jan 16 - Jan 19 just found Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8vWOSuvjmHQNwEgMygE6lgdlMViXBTa-UOr8-WlalA6a) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $1,045 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Really cool modern space Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=_5ljSQ6woMY7TAVHTy4I2OABD7ebMhdfeX8JTuN8WTfYfAZ9r_UIELWNdPFMkU4-) ![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 $1,183 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_Rc1AYL1gE-MyR1X_N7NQSGkX72d3_0R5usFbNrBYe0DE) ![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 $785 per person Jan 16 - Jan 19 just found Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property. Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8vWOSuvjmHQNwEgMygE6lgcs3njy17zb4Ta2MkvBauFg) ![The Blackstone, Autograph Collection](https://images.trvl-media.com/lodging/1000000/30000/22300/22295/5f1a18d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Blackstone, Autograph Collection Downtown Chicago CA $869 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,003 reviews) Best location to stay Reviewed on Oct 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=22295&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_RQsh3i6tnYwKuvmLqaqKIwGZAsFkspcb-NphgHUUtbF-) ## North Side Hotel Deals ![Yelton Manor Bed & Breakfast](https://images.trvl-media.com/lodging/2000000/1480000/1479900/1479840/cbc8aff9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Yelton Manor Bed & Breakfast 140 North Shore Drive, South Haven, MI Fully refundableReserve now, pay when you stay CA $238 CA $264 total Nov 5 - Nov 6 includes taxes & fees 9.2/10 Wonderful! (119 reviews) Good time enjoying the weekend here! Reviewed on Oct 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=1479840&PinnedHotelID=1479840&HadPinnedHotel=true®ionId=948676562717446144) ![Luxury Home on North Beach-NEW Heated Pool & Hot Tub, Firepit, Game Room & More!](https://images.trvl-media.com/lodging/22000000/21480000/21473100/21473034/89544f04_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Luxury Home on North Beach-NEW Heated Pool & Hot Tub, Firepit, Game Room & More! South Haven 9.6/10 Exceptional! (48 reviews) The house was awesome. Nice and really close to the beach. The backyard was really nice. The pool was heated which was nice. Overall just a great place to stay. Reviewed on Sep 28, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=21473034&PinnedHotelID=21473034&HadPinnedHotel=true®ionId=948676562717446144) [](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=21473034&PinnedHotelID=21473034&HadPinnedHotel=true®ionId=948676562717446144) ![Beachfront Luxury Home-NEW Private Heated Pool, Lake View, Firepit, Game Room](https://images.trvl-media.com/lodging/22000000/21390000/21381200/21381188/w3955h2667x45y0-3a453b83_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beachfront Luxury Home-NEW Private Heated Pool, Lake View, Firepit, Game Room South Haven 9.8/10 Exceptional! (48 reviews) Wonderful location, just 200 ft walk to the beach. The owners were very responsive and caring. Wonderful space. Reviewed on Oct 24, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=21381188&PinnedHotelID=21381188&HadPinnedHotel=true®ionId=948676562717446144) [](https://expedia.ca/Hotel-Search?startDate=18%2F11%2F2025&endDate=19%2F11%2F2025&selected=21381188&PinnedHotelID=21381188&HadPinnedHotel=true®ionId=948676562717446144) [See all 2,069 properties in North Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F11%2F2025&endDate=06%2F11%2F2025®ionId=948676562717446144) 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.