Title: Oak Park Vacation Packages & Trips 2026 from CA $1,451 | Expedia.ca [Hotels in Oak Park](https://expedia.ca/Oak-Park-Hotels.d9228.Travel-Guide-Hotels)[Vacation Rentals in Oak Park](https://expedia.ca/Oak-Park-Vacation-Rentals.d9228.Travel-Guide-VacationRentals)[Flights to Oak Park](https://expedia.ca/Cheap-Flights-To-Oak-Park.d9228.Travel-Guide-Flights)[Things to do in Oak Park](https://expedia.ca/Things-To-Do-In-Oak-Park.d9228.Travel-Guide-Activities)[Oak Park Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Park.d9228.Car-Rental-Guide) ![](https://images.trvl-media.com/place/9228/f6f88e06-f8a7-4edb-b5d7-6cc04a9c058c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Oak Park 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 Oak Park Vacation With one of our vacation packages to Oak Park, you'll have endless opportunities for adventure and relaxation. There's a lot to experience, including its chic vibe and rich history. Want to explore your new surroundings? [United Center](https://www.expedia.ca/United-Center-Near-West-Side.d6064077.Vacation-Attraction), [Brookfield Zoo](https://www.expedia.ca/Brookfield-Zoo-Chicago.d6064025.Vacation-Attraction) and [Portage Park](https://www.expedia.ca/Portage-Park-Portage-Park.d6069237.Vacation-Attraction) are just three of the leading places to visit during your trip to Oak Park. No matter your travel plans or budget, putting together the ultimate tailored Oak Park vacation is a walk in the park with Expedia. ## Top Oak Park Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $1,451 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The staff was very kind and check in/out was quick. Great breakfast buffet! Reviewed on Mar 24, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,451 per person May 7 - May 11 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,510 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Rooms are nice, great view, valet parking is great Reviewed on Mar 24, 2026 ![The Wade](https://images.trvl-media.com/lodging/1000000/10000/1400/1346/109a2156_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Wade Downtown Chicago CA $1,573 per person Jun 3 - Jun 8 found 6 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,719 reviews) It’s was an overall nice place Reviewed on Mar 24, 2026 ## Ready to book your vacation to Oak Park? Choose your dates ## Oak Park Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_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 $159 CA $187 total Apr 1 - Apr 2 includes taxes & fees 8/10 Very Good! (10,012 reviews) I wish there was more coffee filters. The vibe was out of The Wild Sheep Chase. Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=9228) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL CA $181 CA $251 total Apr 6 - Apr 7 includes taxes & fees 9.4/10 Exceptional! (3,625 reviews) . Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=06%2F04%2F2026&endDate=07%2F04%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=9228) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL CA $174 CA $205 total Apr 13 - Apr 14 includes taxes & fees 8.6/10 Excellent! (5,762 reviews) This was our first booked trip as a family of 4 and our stay was excellent. Highlight of the stay was the breakfast. We wanted to get to the pool, but it got shut down early Friday night due to an accident. Hotel is in a great spot for walking around and accessing the majority of downtown Chicago. ... Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=9228) [See all 5,003 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=9228) 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 Oak Park ![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 4.5/5(159 reviews) 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 4.5/5(20 reviews) 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) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes 4.5/5(3 reviews) After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.ca/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) ### What to do in Oak Park ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck CA $37 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![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 $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in Oak Park](https://expedia.ca/things-to-do/search?rid=9228) ## 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