Title: Book the Best ROMANTIC Hotels in Chesterton, IN from CA $87 - Chesterton Romantic Getaways | 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)[Chesterton Vacation Packages](https://expedia.ca/Chesterton.d7214.Destination-Travel-Guides) ![Lake Michigan. Path off Trail 9 at one place leads right to the lake. Peaceful to just stand and watch and listen to the waves as they crash to the shore. Trail 9 is the trail to hike if one wants to see the most in the shortest time. Great views throughout the trail. The trail is over 3 miles long and is considered a moderate trail. But certainly worth it. One gets to hike through forest, dunes, and other natural environments and see such a variety of sights. #hiking](https://images.trvl-media.com/place/6091455/985eab23-71e6-415a-af69-65e5707ce659.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ruslian # Find Romantic Hotels in Chesterton, IN from CA $87 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Chesterton Romantic Hotels Tonight [Nov 8 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-08&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Nov 9 - Nov 10](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-09&endDate=2025-11-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=7214&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Top Chesterton Romantic Hotels ![Exterior](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/cf4bd60e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/61001108.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/1b9fd948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Chip Casino Hotel and Spa Michigan City 8.2/10 Very good (1812) "Clean room, easy access to the pool, hot water was wonderful, and staff was very pleasant " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raeanna [](https://www.expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![4 restaurants, dinner served](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/69fa9139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/a7566650.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/70c2b529.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/14000000/13280000/13278700/13278629/9826a884.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Winds Casino Resort – New Buffalo New Buffalo 9.4/10 Exceptional (1591) "Beautiful property and not over crowded! Very friendly staff! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) TAMMY D CA $125 CA $145 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Benton-Harbor-Hotels-Four-Winds-Casino-Resort-New-Buffalo.h13278629.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/b5958a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/6d229925.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Casino](https://images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/eb6189bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ameristar Casino Hotel East Chicago East Chicago 8.6/10 Excellent (1005) "Nice rooms with food options on site. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William [](https://www.expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/e5d5f9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/db40bdb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/b5c04103.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/19000000/18950000/18946600/18946541/6fdf73fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home2 Suites by Hilton Merrillville Merrillville 9.0/10 Wonderful (996) "Wonderful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $134 CA $150 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Merrillville-Hotels-Home2-Suites-By-Hilton-Merrillville.h18946541.Hotel-Information) ![Children's pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/48d008e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Combined shower/tub, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/c6f9a492.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Accessible, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/ac23b9ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/50000/40500/40472/a5decfbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Portage 7.0/10 Good (788) "Would be great if Breakfast area has some decoration. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeff CA $78 CA $87 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Portage-Hotels-Rodeway-Inn.h40472.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/f40c0dc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/4ef2a8bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/c76556f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Spa](https://images.trvl-media.com/lodging/42000000/41830000/41829300/41829276/1a0c074d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pine Lake Resort and Banquets La Porte 6.8/10 (568) "Decent place for a decent price " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $125 CA $144 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/La-Porte-Hotels-Laporte-Hotel-And-Conference-Center.h41829276.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/3d41c4c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/677bdfad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Multiple Beds](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/ff12e260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep-tissue massages, Swedish massages, facials, massages](https://images.trvl-media.com/lodging/28000000/27500000/27490300/27490226/acc04da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Brewery Lodge Hotel Michigan City 9.0/10 Wonderful (779) "Amazing lodge in the forest " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emanuela [](https://www.expedia.ca/Michigan-City-Hotels-The-Brewery-Lodge-Hotel.h27490226.Hotel-Information) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/10000/300/259/2dfb8f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/300/259/b7c2081b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/10000/300/259/85d647a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/300/259/68e970a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Michigan City Inn Michigan City 4.6/10 (1000) "This place is not as advertised and disgusting. Can barely find the entrance, no signs , not landscaped. Another couple in the parking lot said they were tricked too. I want a refund as I left the minute I walked in. Thanks Expedia. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashley CA $126 CA $142 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Michigan-City-Hotels-Ramada-By-Wyndham-Michigan-City.h259.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5008e2fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/83d65721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/25d100a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68930000/68923900/68923845/5b736ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On Lake Shore Drive, Across St From Beach & Beach Stop, Lake MI Views Michigan City 9.6/10 Exceptional (75) "Fabulous, private, quiet. Two minute walk to beach (literally). Well outfitted kitchen. Favorite spot was the porch! Everything needed for a beach vacation was provided. Throughly and absolutely enjoyed our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Katie M. CA $617 CA $716 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Michigan-City-Hotels-On-Lake-Shore-Drive.h68923845.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-11-23&endDate=2025-11-24®ionId=7214&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Chesterton Hotel Reviews ![Blue Chip Casino Hotel and Spa](//images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg) ### Blue Chip Casino Hotel and Spa 10/10 Excellent "Love that you are able to get a snack so late at night! 😊" [](https://expedia.ca/Michigan-City-Hotels-Blue-Chip-Casino-Hotel-And-Spa.h2991209.Hotel-Information) ![Quality Inn Near Interstate I94](//images.trvl-media.com/lodging/2000000/1330000/1320800/1320708/531382df_y.jpg) ### Quality Inn Near Interstate I94 10/10 Excellent "Staff was friendly and the room was comfortable. Hot tub was hot! Just the way I like it." [](https://expedia.ca/Benton-Harbor-Hotels-Quality-Inn-Near-Interstate-I94.h1320708.Hotel-Information) ![Spring House Inn](//images.trvl-media.com/lodging/1000000/810000/809000/808936/51a347fe_y.jpg) ### Spring House Inn 10/10 Excellent "This was the cutest place! The surrounding area is gorgeous! The swings and fire were absolutely lovely! " [](https://expedia.ca/Porter-Hotels-Spring-House-Inn.h808936.Hotel-Information) ![Baymont by Wyndham Michigan City](//images.trvl-media.com/lodging/1000000/30000/21300/21232/6321c49b_y.jpg) ### Baymont by Wyndham Michigan City 10/10 Excellent "Yes" [](https://expedia.ca/Michigan-City-Hotels-Baymont-By-Wyndham-Michigan-City.h21232.Hotel-Information) ![Ameristar Casino Hotel East Chicago](//images.trvl-media.com/lodging/3000000/2520000/2518200/2518162/429a2c05_y.jpg) ### Ameristar Casino Hotel East Chicago 10/10 Excellent "The room was perfect! Clean, spacious and overall very good! The employees also so nice! " [](https://expedia.ca/East-Chicago-Hotels-Ameristar-Casino-Hotel-East-Chicago.h2518162.Hotel-Information) ![Baymont by Wyndham New Buffalo](//images.trvl-media.com/lodging/1000000/870000/867300/867230/6dac1343_y.jpg) ### Baymont by Wyndham New Buffalo 10/10 Excellent "Always a comfy stay" [](https://expedia.ca/Benton-Harbor-Hotels-Baymont-By-Wyndham-New-Buffalo.h867230.Hotel-Information) ![Waterbird Lakeside Inn](//images.trvl-media.com/lodging/3000000/2450000/2450000/2449990/eb33670e_y.jpg) ### Waterbird Lakeside Inn 10/10 Excellent "Loved the balcony overlooking the lake " [](https://expedia.ca/Chesterton-Hotels-Waterbird-Lakeside-Inn.h2449990.Hotel-Information) ![Country Inn & Suites by Radisson, Merrillville, IN](//images.trvl-media.com/lodging/2000000/1360000/1353900/1353808/4d6bf4d2_y.jpg) ### Country Inn & Suites by Radisson, Merrillville, IN 10/10 Excellent "It was a great stay " [](https://expedia.ca/Merrillville-Hotels-Country-Inn-Suites-By-Radisson.h1353808.Hotel-Information) ![Comfort Inn & Suites Porter near Indiana Dunes](//images.trvl-media.com/lodging/4000000/3010000/3003800/3003772/4627aecb_y.jpg) ### Comfort Inn & Suites Porter near Indiana Dunes 10/10 Excellent "Nice and close to the beach." [](https://expedia.ca/Porter-Hotels-Comfort-Inn-Suites-Near-Indiana-Dunes-State-Park.h3003772.Hotel-Information) ## Frequently asked questions ### Searching for romantic hotels in Chesterton? > Are you looking for a romantic vacation? Our guests also enjoy Chesterton for its shopping, restaurants, and beaches. If you'd like to explore some of the area's notable sights, you might make a stop by Indiana Dunes National Park, Lake Michigan, or Lustron House. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Chesterton? > If you're looking forward to lots of outings with your partner, check out these details about year-round temperatures in Chesterton: The hottest months are usually July and August with an average temp of 70°F, while the coldest months are January and February with an average of 31°F. The snowiest months in Chesterton are January, December, November, and February, with each month seeing an average of 6 inches of snowfall. ### What is there to do in Chesterton? > There's nothing better than wandering around a new place with your sweetheart, so consider taking time to discover all that Chesterton has to offer. Couples looking for a little of everything will enjoy Chesterton for its beaches, lakeside setting, and restaurants. Indiana Dunes National Park, Lake Michigan, and Lustron House are worth a stop when you're out and about. ### What's the best way to get to Chesterton and around town during my romantic getaway? > These transportation options in Chesterton might help your romantic trip get off to a smooth start: To get to Chesterton, you can fly into Chicago Midway Airport (MDW), which is the closest major airport, located 37 mi (59.6 km) from the city center. 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