Title: Oak Park Vacation Packages & Trips 2025/2026 from CA $903 | 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/9228/8aa55e4b-7308-4358-afcc-4ab6897c20e0.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. ![The Allegro Royal Sonesta Hotel Chicago Loop](https://images.trvl-media.com/lodging/1000000/40000/34500/34496/69c2e798_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Allegro Royal Sonesta Hotel Chicago Loop Downtown Chicago CA $903 per person Nov 12 - Nov 17 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9/10 Wonderful! (2,027 reviews) I retired from Sonesta working at the corporate office and the Allegro was one of my favorite properties. It is vintage Chicago and it is beautiful. Our room was very clean and it was quiet. The lobby is so pretty. Great area in the Theatre District and very walkable with great restaurants. We will be back again to enjoy this beautiful property. The team does a wonderful job. Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-17/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=34496&paandie=true&dealMarker=DCYSAvhAgzwGnfaJ3fDp-OJAVAmp3JiFoK1e-mGtRXkHbbjxoCBcgyiyha3D7oro) ![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 $987 per person Nov 12 - Nov 17 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9/10 Wonderful! (1,014 reviews) Convenient location for what we were doing. Highly suggested if you are going to a show at the Chicago Theater. Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-17/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=DCYSAvhAgzwGnfaJ3fDp-OJAVAmp3JiFoK1e-mGtRXljdPffG5rj0G3FZkQOy21u) ![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 $1,161 per person Dec 11 - Dec 14 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,714 reviews) The hotel needs a facelift in its rooms. It’s a 5-star hotel, and you expect more. The restaurant was good, and the food was good. On our second day, my server told me a croissant came with my breakfast, but I got charged. I didn’t say anything. On the 20th floor, you can hear everything from outside, like you are on the second floor. No soundproofing? It's hard to sleep at night. Reviewed on Sep 17, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-11/2025-12-14/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=z5Ls6yXaC2Y9IG03Xv4S9IeTatKmnk0aq7Lae1UZkJf4Xm-y3FuZOGHIPD9TzI0-) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,806 per person Nov 7 - Nov 10 found 4 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.6/10 Exceptional! (1,001 reviews) Got pick pocketed in the elevator. I really like this hotel. Plan to return. Reviewed on Sep 8, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-07/2025-11-10/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=F5TIOwhvkCjTPwtoI2vS1iVDRlnnAHF_VHI7mTd2ldPw5ebEKCGvblw4CzsrNOxe) ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/7bca60b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago CA $1,362 per person Nov 12 - Nov 17 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Chicago (ORD) 9.4/10 Exceptional! (1,092 reviews) The room was quite beautiful but there were no robes which would’ve expected. The breakfast was pedestrian nothing special and the server was not good. The front desk staff was excellent. The pool has no umbrellas so it wasn’t possible to use it as it was full sun all day. The outdoor couches on main level were welcome. The restaurant around the corner Maple and Ash. Reviewed on Sep 19, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-12/2025-11-17/?FromAirport=YEG&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=18614145&paandie=true&dealMarker=jHT3N1Ek5bIKLpyRMc9UkZSND9UeVrZQCXtEAnFRy_5ra3o2NqPZpenMVKdRCENc) ## Ready to book your vacation to Oak Park? Choose your dates ## Oak Park Hotel Deals ![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 $240 CA $282 total Sep 22 - Sep 23 includes taxes & fees 8.4/10 Very Good! (4,952 reviews) "Liked convenient location. Nearby transportation facility. Very nice place to stay!" Reviewed on Sep 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=9228) ![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 $204 CA $239 total Sep 22 - Sep 23 includes taxes & fees 7.8/10 Good! (9,218 reviews) "Could use more front desk staff. Quite a line formed behind me" Reviewed on Sep 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=9228) ![Hilton Garden Inn Chicago Downtown/Magnificent Mile](https://images.trvl-media.com/lodging/1000000/430000/424200/424187/d51caee8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Garden Inn Chicago Downtown/Magnificent Mile 10 E Grand Ave, Chicago, IL CA $253 CA $297 total Sep 22 - Sep 23 includes taxes & fees 8.4/10 Very Good! (3,921 reviews) "Everything was great. Downtown location was awesome. Close to everything. We walked to a restaurant. Would definitely stay here again." Reviewed on Sep 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&selected=424187&PinnedHotelID=424187&HadPinnedHotel=true®ionId=9228) [See all 4,892 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=20%2F09%2F2025&endDate=21%2F09%2F2025®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://a.travel-assets.com/findyours-php/viewfinder/images/res70/35000/35620-Wrigley-Field.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) ![Magnificent Mile - River North which includes signage, a city and night scenes](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/23000/23728-Magnificent-Mile.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](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54738-Navy-Pier-Chicago.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 ![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Architecture River Tour CA $67 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details) ![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Color Factory Chicago Ticket CA $47 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Architecture Center River Cruise aboard First Lady CA $77 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.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 ![QR code to download the app](data:image/png;base64,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)