Chesterton Vacations from ￥168,448
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Chesterton Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥214,272, price is now ￥168,448 per person
￥168,448
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.4/10 Exceptional! (317 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
The Westin Michigan Avenue Chicago
Downtown Chicago
Price was ￥371,466, price is now ￥260,622 per person
￥260,622
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Kearney (EAR) to Chicago (ORD)
17.6/10 Exceptional! (1,074 reviews)
I didn’t have breakfast. Just coffee from the Starbucks kiosk.
Reviewed on Nov 17, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥326,377, price is now ￥233,804 per person
￥233,804
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on Nov 17, 2025
Level Chicago – Old Town
Downtown Chicago
Price was ￥250,082, price is now ￥191,525 per person
￥191,525
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Pendry Chicago
Downtown Chicago
Price was ￥224,775, price is now ￥174,228 per person
￥174,228
per person
Jan 25 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Staff was our favorite part! Very very professional and friendly
Reviewed on Nov 14, 2025
Find the Best Chesterton Vacation Packages
Chesterton Hotel Deals
Spring House Inn
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ￥15,300 per night from Nov 24 to Nov 25
￥15,300
￥17,909 total
Nov 24 - Nov 25
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
All around excellent
Reviewed on Nov 10, 2025
Comfort Inn & Suites Porter near Indiana Dunes
1800 West US Highway 20, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is ￥14,165 per night from Nov 19 to Nov 20
￥14,165
￥15,864 total
Nov 19 - Nov 20
includes taxes & fees
8/10 Very Good! (1,000 reviews)
My room was clean and comfortable. I would definitely stay here again
Reviewed on Oct 28, 2025
Best Western Indian Oak
558 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ￥14,449 per night from Nov 24 to Nov 25
￥14,449
￥16,183 total
Nov 24 - Nov 25
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
Our room was clean and spacious! Loved the lake view! Liked the lotion and shampoo! Breakfast was average...wish they'd serve real eggs and make hot oatmeal in the pot. Enjoyed the yogurt machine! Muffins were artificial tasting. Coffee was great!
Reviewed on Nov 10, 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.
