Title: Oakbrook Terrace Vacation Packages & Trips 2026 from CA $571 | 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. ![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 $571 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Amenities, very clean, wonderful buffet service. Reviewed on Dec 20, 2025 ![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 $1,005 per person Feb 13 - Feb 16 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on Dec 18, 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago CA $1,457 per person Mar 15 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Room was spotless and amazing. It was so luxurious and took a bath in the tub with the TV. Appreciated the upgrade and Service. The tea and breakfast were also lovely. It was an amazing stay for Christmas festivities in Chicago. It’s the best hotel! Reviewed on Dec 19, 2025 ![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 $1,383 per person Mar 1 - Mar 7 found 24 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It was smooth and very kind Reviewed on Dec 17, 2025 ![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 $891 per person Mar 15 - Mar 19 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Love staying at the Emily. Very helpful friendly Staff & ccool architecture. Also love the front Patio in Summer☀️ Reviewed on Dec 16, 2025 ## Ready to book your vacation to Oakbrook Terrace? Choose your dates ## Oakbrook Terrace Hotel Deals ![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 $123 CA $145 total Jan 7 - Jan 8, 2026 includes taxes & fees 8.8/10 Excellent! (3,498 reviews) Great location! Nice view, good staff Reviewed on Dec 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=9064) ![Silversmith Hotel Chicago Downtown](https://images.trvl-media.com/lodging/1000000/120000/116700/116674/da03d6b4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Silversmith Hotel Chicago Downtown 10 S Wabash Ave Chicago IL Fully refundableReserve now, pay when you stay CA $112 CA $173 total Dec 30 - Dec 31 includes taxes & fees 9.2/10 Wonderful! (2,139 reviews) Clean, comfortable, convenient. Reviewed on Dec 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=116674&PinnedHotelID=116674&HadPinnedHotel=true®ionId=9064) ![Club Quarters Hotel Wacker at Michigan, Chicago](https://images.trvl-media.com/lodging/1000000/890000/889800/889753/f3eb640d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel Wacker at Michigan, Chicago 75 E Wacker Dr Chicago IL Fully refundableReserve now, pay when you stay CA $105 CA $123 total Dec 24 - Dec 25 includes taxes & fees 8.6/10 Excellent! (2,007 reviews) Easy check in/check out process. Staff was very friendly and helpful. Hotel is conveniently located for walking to shopping, food, and sightseeing Reviewed on Dec 17, 2025 [](https://expedia.ca/Hotel-Search?startDate=24%2F12%2F2025&endDate=25%2F12%2F2025&selected=889753&PinnedHotelID=889753&HadPinnedHotel=true®ionId=9064) [See all 5,093 properties in Oakbrook Terrace](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=21%2F12%2F2025&endDate=22%2F12%2F2025®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 ![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) ![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) ![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 Oakbrook Terrace ![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 **96%** of travellers recommend [](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.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 $281 per adult **80%** of travellers recommend [](https://expedia.ca/things-to-do/city-cruises-chicago-lake-michigan-premier-dinner-cruise.a173241.activity-details) ![Chicago's Navy Pier Centennial Wheel Ticket](https://mediaim.expedia.com/localexpert/48840807/49f0c7f9-d7f7-4281-a580-006a5c5fd53f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago's Navy Pier Centennial Wheel Ticket CA $33 per adult **100%** of travellers recommend [](https://expedia.ca/things-to-do/chicagos-navy-pier-centennial-wheel-ticket.a48840807.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