Title: Oak Park Vacation Packages & Trips 2026/2026 from CA $500 | 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. ![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 $500 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnQpy3rinkRqJM6pDck82oKQPX_8S1FBqtHLePuaS47Jz) ![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 $771 per person Feb 12 - Feb 15 found 8 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=povcxfI1kKc6tB2V7mz6EUxPzJRZ5ezB7Q3KzmYWC39PpUDH4sb7kTiVXJbNFhGH) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $677 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on Dec 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnUWuKAu22NLWLFgtjiKhd7bLIb68mNXa4D0vL3cy5x7Q) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $720 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnUWuKAu22NLWLFgtjiKhd7andWavHTCZ1P8uVZueHruh) ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/b2962364_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $544 per person Feb 12 - Feb 15 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.2/10 Wonderful! (347 reviews) Staff was friendly and outgoing throughout our 2 night stay. Roome were very clean, spacious with floor to ceiling windows and large walk-in showers. Bottle of wine upon check-in. Reviewed on Nov 25, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=95823687&paandie=true&dealMarker=2MaV768TBcz8HM99OhHJ6JqtC1ue5Xc25mNOiXDxEnRrEZRSq7l07ow29QomLjdB) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_9228) ## 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 CA $132 CA $155 total Dec 18 - Dec 19 includes taxes & fees 8.4/10 Very Good! (5,334 reviews) The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ... Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=11580&PinnedHotelID=11580&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 $117 CA $137 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (3,408 reviews) Suite was roomy and spacious, the location wasn’t the best due to high traffic Reviewed on Nov 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=9228) ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Palmer House a Hilton Hotel 17 E Monroe St Chicago IL Fully refundableReserve now, pay when you stay CA $145 CA $205 total Dec 28 - Dec 29 includes taxes & fees 8.4/10 Very Good! (2,111 reviews) Absolutely gorgeous! This hotel offers everything you need and want. Excellent food, amenities and the spa is the best part. We had a mother and daughter weekend with massage's, it was what we hoped for and more. Reviewed on Nov 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=28%2F12%2F2025&endDate=29%2F12%2F2025&selected=8079&PinnedHotelID=8079&HadPinnedHotel=true®ionId=9228) [See all 5,100 properties in Oak Park](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F12%2F2025&endDate=05%2F12%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 ![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 $48 per adult **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details) ![Spirit of Chicago Lunch Cruise](https://mediaim.expedia.com/localexpert/793486/dc2cc19e-2c27-474c-b603-64f1b23a2df6.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Spirit of Chicago Signature Lunch Cruise on Lake Michigan CA $136 per adult [](https://expedia.ca/things-to-do/spirit-of-chicago-signature-lunch-cruise-on-lake-michigan.a793486.activity-details) ![cruise ship sailing past navy pier in chicago](https://mediaim.expedia.com/localexpert/173241/21d8d1a0-e61c-4298-ab2f-118c1794b450.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### City Cruises Chicago: Lake Michigan Premier Dinner Cruise CA $285 per adult **76%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.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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)