Title: Chesterton Vacation Packages & Trips 2026 from CA $1,289 | Expedia.ca [Hotels in Chesterton](https://expedia.ca/Chesterton-Hotels.d7214.Travel-Guide-Hotels)[Vacation Rentals in Chesterton](https://expedia.ca/Chesterton-Vacation-Rentals.d7214.Travel-Guide-VacationRentals)[Things to do in Chesterton](https://expedia.ca/Things-To-Do-In-Chesterton.d7214.Travel-Guide-Activities)[Chesterton Car Rentals](https://expedia.ca/Car-Rentals-In-Chesterton.d7214.Car-Rental-Guide) ![](https://images.trvl-media.com/place/7214/8491ca2c-32fc-492e-8951-4fdfb37580c2.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterton 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 Chesterton Vacation When you organize a vacation package to Chesterton, you can relax and enjoy your getaway knowing that all your travel arrangements have been made in advance. Discover the charms of this lively city from your base in a neighborhood like Miller Beach, which is great for nature. If your trip to Chesterton includes a little sightseeing, check out well-known attractions like [Indiana Dunes State Park](https://www.expedia.ca/Indiana-Dunes-State-Park-Indiana.d6162867.Vacation-Attraction), [Coffee Creek Watershed Conservancy Preserve](https://www.expedia.ca/Coffee-Creek-Watershed-Conservancy-Preserve-Chesterton.d553248621532658879.Vacation-Attraction) and [Portage Lakefront Beach](https://www.expedia.ca/Portage-Lakefront-Beach-Portage.d553248635983989796.Vacation-Attraction). Whatever your travel plans or the size of your budget, organizing your ultimate tailored Chesterton vacation is easy with Expedia. ## Top Chesterton Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,289 per person Jun 18 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 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 20 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 20 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 20 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 Chesterton? Choose your dates ## Chesterton Hotel Deals ![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/527d397d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Indian Oak 558 Indian Boundary Road Chesterton IN Fully refundableReserve now, pay when you stay CA $122 CA $137 total Mar 30 - Mar 31 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) There are many restaurants very close. The rooms were very clean and the one person that shined at this property was a Staff member that cleaned all the rooms and helped guests with all their questions. She alone is a 5 star 🌟 Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=30%2F03%2F2026&endDate=31%2F03%2F2026&selected=49736&PinnedHotelID=49736&HadPinnedHotel=true®ionId=7214) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/2cbab9a1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Spring House Inn 303 N Mineral Springs Rd Chesterton IN Fully refundableReserve now, pay when you stay CA $122 CA $144 total Mar 26 - Mar 27 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) The TV had issues screen mirroring, the gym and pool are underground so pretty small; good interior design and decent breakfast Reviewed on Mar 22, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F03%2F2026&endDate=27%2F03%2F2026&selected=808936&PinnedHotelID=808936&HadPinnedHotel=true®ionId=7214) ![Comfort Inn & Suites Porter near Indiana Dunes](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/c493a250_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Porter near Indiana Dunes 1800 West US Highway 20 Chesterton IN Fully refundable CA $121 CA $135 total Apr 5 - Apr 6 includes taxes & fees 8/10 Very Good! (1,003 reviews) This was easily one of the worst hotel stays I’ve ever survived. Check-in started strong with after waiting 30+ min staff telling me I didn’t even have a reservation of the room with garden tub (shoutout to Expedia for apparently having imaginary photos of rooms). After settling, we got a room that ... Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=3003772&PinnedHotelID=3003772&HadPinnedHotel=true®ionId=7214) [See all 1,423 properties in Chesterton](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%2F2026®ionId=7214) 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) ## 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