
Chesterton Vacation Packages
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- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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, Coffee Creek Watershed Conservancy Preserve and Portage Lakefront Beach. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Chesterton vacation is easy with Expedia.
Top Chesterton Vacation Deals

Hotel Felix River North/Magnificent Mile
Reviewed on Jun 22, 2026

Level Chicago - River North
Reviewed on Jun 19, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Jun 22, 2026

Level Chicago Fulton Market
Reviewed on Jun 20, 2026

Level Chicago – Old Town
Reviewed on Jun 11, 2026
Chesterton Hotel Deals

Best Western Indian Oak
"This was such a peaceful visit and we loved the lakeside room. The pool was a bit dirtier than I would like but I blame that more on other guests than the hotel."
Reviewed on Jun 21, 2026

Spring House Inn
"Just a wonderful stay especially for the price. Hotel is set off the main highway in the woods. We had a king bed room, it was huge and very comfortable with a balcony overlooking the woods. Dining room was very nice and a very good breakfast. Oh yes, indoor heated pool and sauna! Sad we stayed only ..."
Reviewed on Jun 22, 2026

Waterbird Lakeside Inn
"This location is old but clean. It was also very quiet as there seemed to be few customers. We stayed 3 nights while enjoying the convenient location to the Indiana Dunes National Park and a lot of nice restaurant options. The beds were comfortable. It was nice having a balcony overlooking a small ..."
Reviewed on Jun 19, 2026







