Title: Chesterton Vacation Packages & Trips 2025/2026 from CA $706 | 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/7214/1a8c85f0-4e7c-48f9-baa7-58ab4277ea8f.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chesterton Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by City Circus Wandering - ## 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. ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago CA $706 per person Dec 29 - Jan 2 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) The bed was extremly comfortable Staff was very attentive. Highly recommend Reviewed on Oct 7, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRqpisNhNQnL5qYuQW5qL01mYob0TRBmCodyoEVwUJyCp) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $986 per person Dec 22 - Dec 27 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 8.8/10 Excellent! (1,046 reviews) One bad part -drain in tub very slow. Called to fix it but even afterwards still slow. Also room was not cleaned one day, had to call to get it done. Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-27/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=b3fWbLscUsiTNf0BuuZUcBWdhQOq1aATwnk0n_dxQ6ZOb8g3nYPUgFG6DmIIY8Ug) ![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 $1,609 per person Dec 22 - Dec 27 found 1 day ago Roundtrip flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses. Reviewed on Oct 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-22/2025-12-27/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=3cOMQWW2dzwczSvckWVXu8PkdIKHZ2WR16sAbeMXkazQqk6QTHfinTprvFJIiprj) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $707 per person Dec 29 - Jan 2 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (291 reviews) Food price was high but everything was fine Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=8yRry5JRCnY_b9pY3eCEP59MVXltOQBF3gQn1Giukap7ljxFlB29PyTKMknpp0uU) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,300 per person Dec 29 - Jan 2 found 13 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) Awesome room amazing tub even better service Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRhgJAStouzuiJUK1E_1sCmawcHwRwsCSmDjdO2xgz6vG) ## Ready to book your vacation to Chesterton? Choose your dates ## Chesterton Hotel Deals ![Waterbird Lakeside Inn](https://images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterbird Lakeside Inn 556 Indian Boundary Road, Chesterton, IN Fully refundableReserve now, pay when you stay CA $349 CA $391 total Oct 31 - Nov 1 includes taxes & fees 8/10 Very Good! (958 reviews) "Nice, big rooms with a beautiful view of the lake. The room was clean and comfortable. Would recommend for the price." Reviewed on Oct 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=2449990&PinnedHotelID=2449990&HadPinnedHotel=true®ionId=7214) ![Spring House Inn](https://images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_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 $138 CA $162 total Oct 12 - Oct 13 includes taxes & fees 8.8/10 Excellent! (1,008 reviews) "Our stay at the Spring House Inn was fine. It wasn't stellar, it wasn't awful. The place is dated. And every creaking floor tells that story. There is a weird smell throughout - if it's not bleach, it's something floral mixed with bleach and all the halls had Glade Plug Ins in them. Breakfast was ..." Reviewed on Oct 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F10%2F2025&endDate=13%2F10%2F2025&selected=808936&PinnedHotelID=808936&HadPinnedHotel=true®ionId=7214) ![Best Western Indian Oak](https://images.trvl-media.com/lodging/1000000/50000/49800/49736/d30c38a4_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 $130 CA $146 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,004 reviews) "Ac was great, room was spacious and comfortable, patio view was very nice, National and State Park near by, great restaurant selections and some within walking distance. Rooms were clean, plenty of parking, and a very quiet area." Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=49736&PinnedHotelID=49736&HadPinnedHotel=true®ionId=7214) [See all 1,393 properties in Chesterton](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®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 ![QR code to download the app](data:image/png;base64,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)