Title: Oak Lawn Vacation Packages & Trips 2025/2026 from CA $700 | Expedia.ca [Hotels in Oak Lawn](https://expedia.ca/Oak-Lawn-Hotels.d9227.Travel-Guide-Hotels)[Vacation Rentals in Oak Lawn](https://expedia.ca/Oak-Lawn-Vacation-Rentals.d9227.Travel-Guide-VacationRentals)[Things to do in Oak Lawn](https://expedia.ca/Things-To-Do-In-Oak-Lawn.d9227.Travel-Guide-Activities)[Oak Lawn Car Rentals](https://expedia.ca/Car-Rentals-In-Oak-Lawn.d9227.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Oak Lawn 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 Lawn Vacation Experience the unique personality of Oak Lawn with a tailor-made Oak Lawn vacation package. From its welcoming locals to its diversity and beyond, you'll never have a dull moment in this city. Want to explore? [SeatGeek Stadium](https://www.expedia.ca/SeatGeek-Stadium-Chicago.d6131157.Vacation-Attraction), [Chicago Ridge Shopping Mall](https://www.expedia.ca/Chicago-Ridge-Shopping-Mall-Chicago.d6143658.Vacation-Attraction) and [Trinity Christian College](https://www.expedia.ca/Trinity-Christian-College-Chicago.d6143660.Vacation-Attraction) are just a few of the leading places to visit during your trip to Oak Lawn. Whatever your travel plans or budget, organizing a tailored Oak Lawn vacation is a cinch with Expedia. ## Top Oak Lawn Vacation Deals Price found within the past 48 hours. Click for updated prices. ![DoubleTree by Hilton Chicago - North Shore Conference Center](https://images.trvl-media.com/lodging/1000000/20000/15600/15560/8a058213_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### DoubleTree by Hilton Chicago - North Shore Conference Center CA $700 per person Jan 18 - Jan 25 found 21 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.6/10 Excellent! (1,007 reviews) Parkig lot can use some work, repaving . Overall, it was a very pleasant experience. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15560&paandie=true&dealMarker=Mm10hbEKifWBoLbQLYMe_kQ5V3eji1qM-1Nn9vLItK6m4KAxgLHszAC1AKiRGT1b) ![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 $916 per person Dec 29 - Jan 3 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9/10 Wonderful! (367 reviews) Easy check-in, friendly staff, beautiful building with nice amenities. Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6DiTc4OIWqbvTDOXf_yD6dwqYevmwF3n0Cfcg5Bgc90n) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $1,230 per person Jan 18 - Jan 25 found 21 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (2,141 reviews) It needs improvement Reviewed on Oct 28, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-18/2026-01-25/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=8058&paandie=true&dealMarker=yrZ0TBn6Yd3hsppSaARbbxkR2YhhqyiysHHSCHR7US_OgYKb17BpuOeDbYGG5u3W) ![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 $1,405 per person Nov 29 - Dec 2 found 14 hours ago Roundtrip flight included Toronto (YTZ) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump never disappoints, always friendly, clean, and top notch service. We stay several times a year, they make you feel right at home. Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-29/2025-12-02/?FromAirport=YTZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=4ehT1aRAgqfqNoUNYgNbtGea_RkIHQkVj7Ot40Xv8HnNeFlqhyF06NhM3U5pWJuH) ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $946 per person Dec 29 - Jan 3 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (721 reviews) Clean and seemed fairly new, nice staff and great location Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-03/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=2iNwDrKkiFnmTHALAc1c6KvjJBk8vlllWTJdJg7UgG6HqBrWrUKqkO8UlDRa5Vvq) ## Ready to book your vacation to Oak Lawn? Choose your dates ## Oak Lawn 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 $177 CA $208 total Nov 16 - Nov 17 includes taxes & fees 8.4/10 Very Good! (5,162 reviews) We enjoyed our stay, great location for walking around downtown. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=9227) ![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 $131 CA $154 total Nov 24 - Nov 25 includes taxes & fees 7.8/10 Good! (9,611 reviews) Great Reviewed on Oct 28, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F11%2F2025&endDate=25%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=9227) ![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Freehand Chicago 19 East Ohio Street, Chicago, IL Fully refundableReserve now, pay when you stay CA $95 CA $137 total Nov 26 - Nov 27 includes taxes & fees 7.8/10 Good! (2,533 reviews) Excellent location close to everything. Room with a double bed was small but had a nice bathroom. Nice and friendly staff. Reviewed on Oct 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F11%2F2025&endDate=27%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true®ionId=9227) [See all 4,625 properties in Oak Lawn](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=29%2F10%2F2025&endDate=30%2F10%2F2025®ionId=9227) 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 Lawn ![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 Lawn ![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/49191714/1b6e1be3-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) [See all activities in Oak Lawn](https://expedia.ca/things-to-do/search?rid=9227) ## 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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)