Title: Countryside Vacation Packages & Trips 2026 from CA $707 | Expedia.ca [Hotels in Countryside](https://expedia.ca/Countryside-Hotels.d7682.Travel-Guide-Hotels)[Vacation Rentals in Countryside](https://expedia.ca/Countryside-Vacation-Rentals.d7682.Travel-Guide-VacationRentals)[Things to do in Countryside](https://expedia.ca/Things-To-Do-In-Countryside.d7682.Travel-Guide-Activities)[Countryside Car Rentals](https://expedia.ca/Car-Rentals-In-Countryside.d7682.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7682/cd4c1227-caac-45f0-8c9d-be27fbc471fc.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Countryside 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 Countryside Vacation Book a Countryside vacation package and get set for a wonderful adventure. Known for its rural countryside and spectacular views, there's plenty to keep you on the move in this fascinating city. If your trip to Countryside includes a little sightseeing, take in famous attractions like [Brookfield Zoo](https://www.expedia.ca/Brookfield-Zoo-Chicago.d6064025.Vacation-Attraction), [SeatGeek Stadium](https://www.expedia.ca/SeatGeek-Stadium-Chicago.d6131157.Vacation-Attraction) and [Chicago Ridge Shopping Mall](https://www.expedia.ca/Chicago-Ridge-Shopping-Mall-Chicago.d6143658.Vacation-Attraction). Browse Expedia's wide range of travel options and start planning your dream vacation to Countryside now. ## Top Countryside Vacation Deals Price found within the past 48 hours. Click for updated prices. ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago CA $707 per person May 1 - May 3 found 13 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) Bottle of waters were not stocked in the refrigerator. Reviewed on Jan 6, 2026 ![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 $743 per person Apr 9 - Apr 12 found 1 day 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 $828 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Everything was amazing, specially the breakfast buffet. Reviewed on Feb 7, 2026 ![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 $708 per person Apr 17 - Apr 20 found 1 day ago Roundtrip flight included Montreal Metropolitan Airport (YHU) to Chicago (ORD) 9/10 Wonderful! (766 reviews) Great stay. Would come again. Reviewed on Jan 19, 2026 ![Holiday Inn Club Vacations at Lake Geneva Resort by IHG](https://images.trvl-media.com/lodging/2000000/1690000/1681300/1681285/bf062b0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Club Vacations at Lake Geneva Resort by IHG CA $723 per person Apr 21 - Apr 25 found 17 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.8/10 Excellent! (1,003 reviews) My room was very clean, which I appreciated. We booked a suite, but the first one opened directly into the bedroom, and being on the first floor, I didn’t feel comfortable with that layout. I requested a room change, and the staff handled it quickly and professionally, which I really appreciated. One thing that was a bit confusing was the inconsistency between suites—some had a full kitchen while others only had a range top. It would be helpful to know that in advance when booking. Overall, the stay was quiet and peaceful during the week, which was exactly what we wanted. When we arrived on Saturday afternoon, the atmosphere was completely different—lots of people, plenty of activity, and a lively environment. The only real downside was that the room felt drafty. We ended up putting a towel under the door to help block the cold air. Aside from those small issues, it was a comfortable stay with a good stay. Reviewed on Jan 16, 2026 ## Ready to book your vacation to Countryside? Choose your dates ## Countryside Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay CA $122 CA $143 total Feb 8 - Feb 9 includes taxes & fees 8/10 Very Good! (9,839 reviews) Great a+++ Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=7682) ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago 720 S Michigan Ave Chicago IL Fully refundableReserve now, pay when you stay CA $190 CA $263 total Feb 21 - Feb 22 includes taxes & fees 8.4/10 Very Good! (2,597 reviews) Some of the nicest people you'll ever meet! Excellent location for a Bears game stay, walking distance to Soldier Field. Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=12570&PinnedHotelID=12570&HadPinnedHotel=true®ionId=7682) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay CA $140 CA $165 total Feb 24 - Feb 25 includes taxes & fees 8.4/10 Very Good! (5,637 reviews) Yes room was spotless Reviewed on Feb 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F02%2F2026&endDate=25%2F02%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=7682) [See all 5,093 properties in Countryside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=7682) 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) ### Discover the most popular places to visit in Countryside ![Wrigley Field featuring central business district, a city and a sporting event](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.ca/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.ca/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.ca/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### What to do in Countryside ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $53 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/feac7bb1-c7ea-4b19-8342-818eafa34e83.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) [See all activities in Countryside](https://expedia.ca/things-to-do/search?rid=7682) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app