Title: Oak Park Vacation Packages & Trips 2026 from CA $739 | 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. ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/46b44b35_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $739 per person Apr 26 - Apr 30 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (858 reviews) I would stay here again without a second thought. Great Reviewed on Mar 11, 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 $1,131 per person May 22 - May 25 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,438 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 ![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### LondonHouse Chicago, Curio Collection by Hilton Downtown Chicago CA $2,248 per person Jun 3 - Jun 9 found 23 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (3,613 reviews) Clean room, perfect location Reviewed on Mar 11, 2026 ![Hyatt Place Chicago/Downtown - The Loop](https://images.trvl-media.com/lodging/12000000/11070000/11062300/11062225/57098577_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hyatt Place Chicago/Downtown - The Loop Downtown Chicago CA $1,320 per person Jun 4 - Jun 7 found 11 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 8.8/10 Excellent! (1,201 reviews) We flew all night and were very tired when we arrived at the property. We were so grateful to be able to check in early. Reviewed on Mar 9, 2026 ![The Buckingham Hotel](https://images.trvl-media.com/lodging/2000000/1120000/1112300/1112252/9f1dce74_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Buckingham Hotel Downtown Chicago CA $2,027 per person Jun 3 - Jun 9 found 7 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9/10 Wonderful! (1,000 reviews) Price was great. Room was huge with such a beautiful view of the city. Also a safe location within walking distance of things to see and do Reviewed on Mar 5, 2026 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_9228) ## 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 $131 CA $154 total Apr 1 - Apr 2 includes taxes & fees 8/10 Very Good! (9,944 reviews) I didn’t have any hot water for the first 36 hours or so. There is no WiFi. The TV has around 15 channels but no remote. Neither of the restaurants were open during my 3 day stay. Beds are super hard. Reviewed on Mar 11, 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 Fully refundableReserve now, pay when you stay CA $179 CA $249 total Mar 30 - Mar 31 includes taxes & fees 9.4/10 Exceptional! (3,511 reviews) Everyone that we encountered at the hotel was so helpful and so nice. Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%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 Fully refundableReserve now, pay when you stay CA $166 CA $195 total Mar 22 - Mar 23 includes taxes & fees 8.6/10 Excellent! (5,728 reviews) Breakfast menu had great options for a family of five. Room was clean. I really like being able to text someone from the front desk to get questions answered. The location is excellent as well. Will definitely stay here again. Reviewed on Mar 11, 2026 [](https://expedia.ca/Hotel-Search?startDate=22%2F03%2F2026&endDate=23%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=9228) [See all 5,103 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F03%2F2026&endDate=14%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(158 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(19 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) ![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 4.5/5(459 reviews) 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 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 $36 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/360-chicago-observation-deck.a170348.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) ![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) [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