Chesterton Vacation Packages
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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
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was CA $1,003, price is now CA $755 per person
CA $755
per person
Jun 22 - Jun 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!
Reviewed on May 5, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,968, price is now CA $1,453 per person
CA $1,453
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!
Reviewed on Apr 27, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was CA $1,123, price is now CA $834 per person
CA $834
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (2,281 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.
Reviewed on May 5, 2026
Chesterton Hotel Deals
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from May 28 to May 29
CA $163
CA $189 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Notice it wasn’t as nice as previous stays. No hot chocolate, not much for breakfast, etc. BUT woke up to mice and mice poop took it over the edge.
Reviewed on May 5, 2026
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from May 25 to May 26
CA $128
CA $143 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Breakfast was as usual , something for everyone
Reviewed on May 7, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from May 10 to May 11
CA $124
CA $139 total
May 10 - May 11
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
Yes
Reviewed on May 7, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
