Title: Oak Park Vacation Packages & Trips 2025/2026 from CA $445 | 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/6064079/39b52f5e-4604-4c38-8ea1-1de738b49e4d.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. ![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 $445 per person Jan 16 - Jan 19 found 15 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel Reviewed on Oct 20, 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=2463437&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8vjUKXs13L6ETapVSeqoyF4_8L4xB4f5QXzl8P1oMi7O) ![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 found 15 hours ago 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=EdX7Rh5nPMXgi2lS0rhe8lUQ-kCz-sibwP2Ovz_sWEeYK4QvMsAXqY3TKNQwupNm) ![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 found 15 hours ago 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=EdX7Rh5nPMXgi2lS0rhe8lUQ-kCz-sibwP2Ovz_sWEcmHuR8Abh2lpNfGKWSCNwA) ![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 $544 per person Jan 16 - Jan 19 found 15 hours 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/2026-01-16/2026-01-19/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=EdX7Rh5nPMXgi2lS0rhe8lUQ-kCz-sibwP2Ovz_sWEcIvcA90Av5pE8vAHqON0Lh) ![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 $1,450 per person Dec 29 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=diCbnW5ysK4gVhqmD_TxzsoM9GwPCGbZOuY073TSeAxKF2RKhtPoDe4gLljSHjK8) ## 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 $167 CA $196 total Nov 23 - Nov 24 includes taxes & fees 8.4/10 Very Good! (5,182 reviews) Everything was perfect will definitely stay again . Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=23%2F11%2F2025&endDate=24%2F11%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 $132 CA $155 total Nov 24 - Nov 25 includes taxes & fees 7.8/10 Good! (9,677 reviews) I love the classical charm of this hotel. High ceiling rooms, curved walls. The staff are friendly and efficient, even though they were handling guests in for at least two major events. Minor quibbles are the drink was very expensive at the bar, the noise beteeen rooms is loud (we used ear plugs ... Reviewed on Nov 4, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=9228) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl, Chicago, IL Fully refundableReserve now, pay when you stay CA $143 CA $167 total Nov 17 - Nov 18 includes taxes & fees 8.8/10 Excellent! (3,220 reviews) Great staff at the front desk! Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F11%2F2025&endDate=18%2F11%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=9228) [See all 5,014 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=06%2F11%2F2025&endDate=07%2F11%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 $68 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/architecture-river-tour.a170432.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 $78 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.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 **94%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.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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)