Title: Darien Vacation Packages & Trips 2026 from CA $1,158 | Expedia.ca [Hotels in Darien](https://expedia.ca/Darien-Hotels.d181404.Travel-Guide-Hotels)[Vacation Rentals in Darien](https://expedia.ca/Darien-Vacation-Rentals.d181404.Travel-Guide-VacationRentals)[Flights to Darien](https://expedia.ca/Cheap-Flights-To-Darien.d181404.Travel-Guide-Flights)[Darien Car Rentals](https://expedia.ca/Car-Rentals-In-Darien.d181404.Car-Rental-Guide) ![](https://images.trvl-media.com/place/181404/949ec324-afc4-4b19-8658-f764d8898945.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Darien 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 Darien Vacation There's tons to love about Darien, from its rich history to its spectacular views. When you're ready to spend some time in this captivating city, our Darien vacation packages will be perfect for you. If your trip to Darien includes some sightseeing, hit up well-known attractions like [Morton Arboretum](https://www.expedia.ca/Morton-Arboretum-Chicago.d6238155.Vacation-Attraction), [Promenade Bolingbrook](https://www.expedia.ca/Promenade-Bolingbrook-Chicago.d6138534.Vacation-Attraction) and [Cog Hill Golf & Country Club](https://www.expedia.ca/Cog-Hill-Golf-Country-Club-Chicago.d553248621532658527.Vacation-Attraction). Whatever your travel plans or budget, organizing a tailored Darien vacation is easy with Expedia. ## Top Darien Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $1,158 per person May 8 - May 13 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (2,091 reviews) Clean room and great staff! Reviewed on Mar 24, 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 $1,451 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The rooftop wasn’t open, everything else was great Reviewed on Mar 24, 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 $1,510 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) This was a nice hotel but some staff made us feel uncomfortable and the rooms had flaws (dirt). I expected better for the money however, I met someone who stayed at Travelodge and their hotel flooded. So, I'd recommend this hotel. Reviewed on Mar 23, 2026 ![Staypineapple, An Iconic Hotel, The Loop](https://images.trvl-media.com/lodging/1000000/290000/284800/284792/bbf9e380_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Staypineapple, An Iconic Hotel, The Loop Downtown Chicago CA $1,474 per person Jun 4 - Jun 8 found 23 hours ago Roundtrip flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,021 reviews) I would have rated all 5 star but the restaurant Atwood was closed and we weren’t notified in time to change plans! The staff and (Mr.Brown ) were extremely accommodating! It was my bday and they decorated our room with all sorts of goodies including a hand made stuffed wash cloth doggie! Our housekeeper was amazing too! The room decor is such fun and extremely clean! The only drawback is the rooms are very small and some not configured well! All and all it’s a wonderful place to experience!!!!🍍 Reviewed on Mar 18, 2026 ## Ready to book your vacation to Darien? Choose your dates ## Darien 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 $159 CA $187 total Mar 25 - Mar 26 includes taxes & fees 8/10 Very Good! (10,008 reviews) The room is cozy and decent Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=25%2F03%2F2026&endDate=26%2F03%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=181404) ![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 CA $179 CA $210 total Apr 5 - Apr 6 includes taxes & fees 8.6/10 Excellent! (5,786 reviews) Wonderful stay Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=181404) ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/a48bf16b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago O'Hare Airport O'Hare International Airport Chicago IL Fully refundableReserve now, pay when you stay CA $314 CA $368 total Apr 24 - Apr 25 includes taxes & fees 8.4/10 Very Good! (2,233 reviews) Clean room and friendly staff Reviewed on Mar 21, 2026 [](https://expedia.ca/Hotel-Search?startDate=24%2F04%2F2026&endDate=25%2F04%2F2026&selected=8058&PinnedHotelID=8058&HadPinnedHotel=true®ionId=181404) [See all 3,861 properties in Darien](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=181404) 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 Darien ![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 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) ![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 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) ![Chicago Skyline at North Beach](https://images.trvl-media.com/place/6069213/e3e08680-ba57-4e08-8e19-fef490757e5e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Naval Base Great Lakes 4.5/5(3 reviews) 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 Darien ![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) ![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wendella's 90-min Chicago River Architecture Tour CA $55 per adult **94%** of travellers recommend [](https://expedia.ca/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago CA $52 per adult **98%** of travellers recommend [](https://expedia.ca/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in Darien](https://expedia.ca/things-to-do/search?rid=181404) ## 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