Title: Oakbrook Terrace Vacation Packages & Trips 2026 from CA $1,255 | Expedia.ca [Oakbrook Terrace Travel Guide](https://expedia.ca/Oakbrook-Terrace.dx9064)[Hotels in Oakbrook Terrace](https://expedia.ca/Oakbrook-Terrace-Hotels.d9064.Travel-Guide-Hotels)[Vacation Rentals in Oakbrook Terrace](https://expedia.ca/Oakbrook-Terrace-Vacation-Rentals.d9064.Travel-Guide-VacationRentals)[Oakbrook Terrace Car Rentals](https://expedia.ca/Car-Rentals-In-Oakbrook-Terrace.d9064.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) # Oakbrook Terrace 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 ## Top Oakbrook Terrace Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/28e8042f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $1,255 per person Apr 28 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,140 reviews) Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special! Reviewed on Mar 16, 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 $1,452 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) It was in a perfect spot for us to visit Chicago and have a comfortable place to stay Reviewed on Mar 21, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,504 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great location, views, & amenities. Reviewed on Mar 20, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,289 per person Jun 5 - Jun 8 found 17 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Spacious room with great views and washer and dryer Reviewed on Mar 17, 2026 ![Hilton Garden Inn Chicago Central Loop](https://images.trvl-media.com/lodging/69000000/68110000/68102900/68102882/w3837h2621x0y0-5bb1f388_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Chicago Central Loop Downtown Chicago CA $1,458 per person Jun 4 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,300 reviews) It was a good place to spend a staycation weekend. Well located and friendly staff Reviewed on Mar 16, 2026 ## Ready to book your vacation to Oakbrook Terrace? Choose your dates ## Oakbrook Terrace 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 $143 CA $168 total Apr 1 - Apr 2 includes taxes & fees 8/10 Very Good! (9,978 reviews) No hot water in the room Reviewed on Mar 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F04%2F2026&endDate=02%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=9064) ![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 $189 CA $260 total Mar 29 - Mar 30 includes taxes & fees 9.4/10 Exceptional! (3,582 reviews) The view from my 22nd floor room was great, the breakfast buffet was fantastic and the bed was comfortable. There is one thing that could be improved, however. When I got in I was desperate for a caffeine fix. I do not drink coffee, only tea. However, there was no tea bag with the coffee maker, only ... Reviewed on Mar 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=9064) ![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 $179 CA $210 total Mar 29 - Mar 30 includes taxes & fees 8.6/10 Excellent! (5,758 reviews) Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again. Reviewed on Mar 20, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=9064) [See all 4,936 properties in Oakbrook Terrace](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F03%2F2026&endDate=23%2F03%2F2026®ionId=9064) 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 Oakbrook Terrace ![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 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 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) ![View of Chicago skyline at sunrise.](https://images.trvl-media.com/place/6069213/7912338a-cac5-4762-9012-728b8bea99be.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area. [](https://expedia.ca/Naval-Base-Great-Lakes-Chicago.d6069213.Vacation-Attraction) ### What to do in Oakbrook Terrace ![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) ![Art Institute of Chicago](https://mediaim.expedia.com/localexpert/170360/cfa59fea-c028-46b9-93be-ea78b723f52e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Art Institute of Chicago CA $55 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/art-institute-of-chicago.a170360.activity-details) ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission CA $60 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) [See all activities in Oakbrook Terrace](https://expedia.ca/things-to-do/search?rid=9064) ## 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