Title: Chesterton Vacation Packages 2026 from $185 | Expedia.com [Chesterton Travel Guide](https://expedia.com/Chesterton.dx7214)[Hotels in Chesterton](https://expedia.com/Chesterton-Hotels.d7214.Travel-Guide-Hotels)[Vacation Rentals in Chesterton](https://expedia.com/Chesterton-Vacation-Rentals.d7214.Travel-Guide-VacationRentals)[Flights to Chesterton](https://expedia.com/Cheap-Flights-To-Chesterton.d7214.Travel-Guide-Flights)[Things to do in Chesterton](https://expedia.com/Things-To-Do-In-Chesterton.d7214.Travel-Guide-Activities)[Car Rentals in Chesterton](https://expedia.com/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 Vacations from $185 ## Book a Hotel + Flight or Car together to unlock savings ## 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.com/Indiana-Dunes-State-Park-Indiana.d6162867.Vacation-Attraction), [Coffee Creek Watershed Conservancy Preserve](https://www.expedia.com/Coffee-Creek-Watershed-Conservancy-Preserve-Chesterton.d553248621532658879.Vacation-Attraction) and [Portage Lakefront Beach](https://www.expedia.com/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. ## The Latest Chesterton vacation packages Price found within the past 48 hours. Click for updated prices. ![Red Roof Inn PLUS+ Chicago - Willowbrook](https://images.trvl-media.com/lodging/1000000/10000/4100/4013/dd62fe20_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Red Roof Inn PLUS+ Chicago - Willowbrook Save 100% on your flight $185 per person May 14 - May 18 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 6.4/10 (1,004 reviews) Check in was quick and simple. The room was clean and that's all i needed for a few hours until i went to the airport. The extra lock on the,door was broken. There also was a coffee pot, but no coffee in the room Reviewed on Feb 8, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago Save 100% on your flight $463 per person Apr 23 - Apr 27 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (380 reviews) First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon! Reviewed on Feb 19, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel Save 100% on your flight $311 per person May 4 - May 7 found 23 hours ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 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 $484 per person Apr 28 - May 1 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money. Reviewed on Feb 20, 2026 ![Viceroy Chicago](https://images.trvl-media.com/lodging/19000000/18620000/18614200/18614145/3aeed14b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Viceroy Chicago Downtown Chicago Save 100% on your flight $723 per person Apr 22 - Apr 26 found 23 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (1,129 reviews) We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend. Reviewed on Feb 15, 2026 Don't see what you're looking for? See all available trips from Columbus to Chesterton [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-20/2026-03-27/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=RFD&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_7214) ### Discover the most popular places to visit in Chesterton ![Indiana Dunes State Park which includes a sandy beach and general coastal views as well as a family](https://images.trvl-media.com/place/6162867/8e516814-0d8a-4c1c-bd54-098810d910c5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Indiana Dunes State Park 4.5/5(185 reviews) The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming. [](https://expedia.com/Indiana-Dunes-State-Park-Chesterton.d6162867.Vacation-Attraction) ![Indiana Dunes National Park Sign](https://images.trvl-media.com/place/553248635998150039/1179bf39-711c-4b74-aec4-01645a90932f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Indiana Dunes Visitor Center Explore the great outdoors at Indiana Dunes Visitor Center, a lovely green space in Porter. Wander the beaches and forest in this family-friendly area. [](https://expedia.com/Indiana-Dunes-Visitor-Center-Chesterton.d553248635998150039.Vacation-Attraction) ![Coffee Creek Watershed Conservancy sign in Chesterton, Indiana USA ](https://images.trvl-media.com/place/553248621532658879/68ccfb1d-2601-4897-8f08-c4329f9dc662.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Coffee Creek Watershed Conservancy Preserve 3.5/5(2 reviews) Explore the great outdoors at Coffee Creek Watershed Conservancy Preserve, a lovely green space in Chesterton. Wander the area's beautiful beaches or simply enjoy one of its charming coffeehouses. [](https://expedia.com/Coffee-Creek-Watershed-Conservancy-Preserve-Chesterton.d553248621532658879.Vacation-Attraction) ## Chesterton Hotel Deals ![Comfort Inn & Suites Porter near Indiana Dunes](https://images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Inn & Suites Porter near Indiana Dunes 1800 West US Highway 20 Chesterton IN Fully refundableReserve now, pay when you stay $80 nightly $90 total Feb 23 - Feb 24 Total with taxes and fees 8/10 Very Good! (1,002 reviews) Room was very dirty and the staff was very unprofessional they made me change rooms all because a lady was yelling at them. The window seal is broken making the room very cold Reviewed on Feb 8, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F23%2F2026&endDate=2%2F24%2F2026&selected=3003772&PinnedHotelID=3003772&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 $83 nightly $93 total Feb 22 - Feb 23 Total with taxes and fees 8.8/10 Excellent! (1,002 reviews) This is a super cute Inn nestled in some woods. We were greeted by a family of deer right outside our room. Room was clean, quiet and affordable! Felt more like a State Park Inn. Reviewed on Feb 16, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=808936&PinnedHotelID=808936&HadPinnedHotel=true®ionId=7214) ![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 $76 nightly $86 total Feb 22 - Feb 23 Total with taxes and fees 8.2/10 Very Good! (999 reviews) Things were okay. Reviewed on Feb 20, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%2F2026&selected=2449990&PinnedHotelID=2449990&HadPinnedHotel=true®ionId=7214) [See all 1,411 properties in Chesterton](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F21%2F2026&endDate=2%2F22%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. ## Find the Best Chesterton Vacation Packages ### Things to do in and around Chesterton Chesterton, Indiana, offers a perfect blend of outdoor adventure and scenic beauty. Visitors can explore popular attractions like local parks, enjoy nature walks, and take advantage of biking trails. The recreational areas and playgrounds make it an ideal destination for families, while nature enthusiasts will appreciate the opportunity for little sightseeing and exploration of the area's natural landscapes. **Shopping** In Chesterton, you can shop at local boutiques and specialty stores. If you're up for a drive, visit [Lighthouse Place Premium Outlets](https://www.expedia.com/Lighthouse-Place-Premium-Outlets-Michigan-City.d6130013.Vacation-Attraction) for a variety of shops, or explore [Westfield Southlake Mall](https://www.expedia.com/Westfield-Southlake-Mall-Green-Acres.d6162863.Vacation-Attraction) for more options and entertainment. [Garwood Orchards](https://www.expedia.com/Garwood-Orchards-La-Porte.d787093278121676800.Vacation-Attraction) offers unique gifts and local produce. **Recreation** Explore [Marquette Park](https://www.expedia.com/Marquette-Park-Miller-Beach.d553248621532658632.Vacation-Attraction) for a serene day surrounded by nature, perfect for relaxation and mindfulness. Experience the charm of [Chicago Street Theatre](https://www.expedia.com/Chicago-Street-Theatre-Valparaiso.d553248621532658864.Vacation-Attraction) for an evening filled with culture and entertainment. For outdoor enthusiasts, enjoy a round of disc golf at the nearby Disc Golf Course, embracing friendly competition. **Adventure** Experience thrills at [Deep River Water Park](https://www.expedia.com/Deep-River-Water-Park-Crown-Point.d6162869.Vacation-Attraction), located 13 miles from Chesterton, where you can enjoy exciting water slides and family fun. For an adrenaline rush, visit [Team Combat LIVE](https://www.expedia.com/Team-Combat-LIVE-Green-Acres.d553248621532658477.Vacation-Attraction), 14 miles away, featuring immersive arcade battles. Don’t miss the scenic Cowles Bog Trailhead, perfect for hiking right in Chesterton. **Nightlife** Experience a unique nightlife in Chesterton with a visit to the [Round Barn Union Pier Tasting Room](https://www.expedia.com/Round-Barn-Union-Pier-Tasting-Room-Union-Pier.d553248621532658901.Vacation-Attraction), located 25 miles away. Enjoy a cozy pub atmosphere filled with entertainment and romantic vibes, perfect for unwinding after a day of exploration. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions in and around Chesterton Chesterton, Indiana, is a fantastic destination for outdoor enthusiasts and families alike, offering beautiful scenery and adventure opportunities. Visitors can explore the stunning beaches and trails of the nearby Indiana Dunes National Park, as well as enjoy the local urban parks. With various attractions catering to outdoor activities and family experiences, Chesterton promises a memorable getaway for all types of travelers. - **[Indiana Dunes National Park: ](https://www.expedia.com/Indiana-Dunes-National-Park-Indiana.d6091455.Vacation-Attraction)** Just 3 miles from Chesterton, this national park offers breathtaking scenery and a variety of outdoor adventures. Explore miles of sandy beaches, hike scenic trails, and enjoy the diverse ecosystems that make this park a natural wonder. - **[Lake View Beach: ](https://www.expedia.com/Lake-View-Beach-Michigan-City.d553248635983993933.Vacation-Attraction)** Located 6 miles away, Lake View Beach is a serene spot perfect for relaxing under the sun. With its soft sands and stunning views of Lake Michigan, it’s an ideal place for swimming, picnicking, or simply soaking in the beach vibes. - **[Indiana Dunes Visitor Center: ](https://www.expedia.com/Indiana-Dunes-Visitor-Center-Chesterton.d553248635998150039.Vacation-Attraction)** Situated within Chesterton, this visitor center is your gateway to adventure. Families can learn about the park's natural history and find resources for exploring the surrounding outdoor wonders, making it a great starting point for your trip. ### Tips to save on your trip to Chesterton - Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings. - Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Chesterton. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Chesterton Essential Information | Language | English | | --------------- | --------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 13,400 | | Max Temp Winter | 30ºF | | Max Temp Summer | 75ºF | | Top Sights | [Indiana Dunes National Park](https://www.expedia.com/Indiana-Dunes-National-Park-Indiana.d6091455.Vacation-Attraction), [Indiana Dunes State Park](https://www.expedia.com/Indiana-Dunes-State-Park-Indiana.d6162867.Vacation-Attraction) and [Lake View Beach](https://www.expedia.com/Lake-View-Beach-Michigan-City.d553248635983993933.Vacation-Attraction) | ## More vacations you might like 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Savings not available on all packages.