Chesterton Vacations from ￥252,916
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The Latest Chesterton Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North
Downtown Chicago
Price was ￥294,574, price is now ￥252,916 per person
￥252,916
per person
Mar 29 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,159 reviews)
Great location. Good size room. Restaurant was awesome.
Reviewed on Jan 9, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥334,992, price is now ￥259,064 per person
￥259,064
per person
Mar 29 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great breakfast, Clean room, enjoyed the stay
Reviewed on Jan 9, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥294,481, price is now ￥254,092 per person
￥254,092
per person
Mar 29 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Clean room, amazinggggg views, everyone was so nice. Must go downstairs to Toro and get a martini from John!!
Reviewed on Jan 10, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥293,314, price is now ￥253,315 per person
￥253,315
per person
Mar 29 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Everything was soooo amazing, especially the staff
Reviewed on Jan 10, 2026
The Emily Hotel
Downtown Chicago
Price was ￥319,399, price is now ￥278,176 per person
￥278,176
per person
Mar 29 - Apr 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was spacious and the amenities great.
Food was good both at the cafe and in the restaurant.
Good location
Reviewed on Jan 9, 2026
Find the Best Chesterton Vacation Packages
Chesterton Hotel Deals
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20 Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ￥14,474 per night from Feb 1 to Feb 2
￥14,474
￥16,211 total
Feb 1 - Feb 2
includes taxes & fees
8/10 Very Good! (1,001 reviews)
Great staff and hospitality! Everything was clean and tidy.
Reviewed on Nov 28, 2025
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ￥12,473 per night from Jan 12 to Jan 13
￥12,473
￥14,759 total
Jan 12 - Jan 13
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
The stay was amazing! This is one of my favorite hotels esp for an affordable getaway for two 😇 breakfast is great, rooms are clean, very comfy and cozy. Porches are great esp overlooking the woods. Only downside, no late checkout option, and then the coffee was not the greatest. Not sure if it ...
Reviewed on Jan 5, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
8/10 Very Good! (992 reviews)
My room is nice & cozy.
Reviewed on Dec 31, 2025
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.
Discover the most popular places to visit in Chesterton
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.
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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.
