Chesterton Vacations from ￥273,916
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The Latest Chesterton Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥356,454, price is now ￥273,916 per person
￥273,916
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
The hotel is nice. Not luxurious, not fully equipped, but well located. It is definitely understaffed since the same person handles the front office and the breakfast/drinks in the morning, and the front office and bar in the evening. But they manage well and are extremely nice. Shoutout to Marina who was very helpful.
It is rather clean, though we had to request our room to be cleaned on the 2nd day as they hadn’t done it on the first day.
The breakfast options are not great, only 5-6 options are available and they’re all pastries. They have some fruits as well. Overall the stay was good but I wouldn’t go back.
Reviewed on Feb 24, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥464,008, price is now ￥278,428 per person
￥278,428
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Loved the hotel and ambiance. My stay was truly amazing. I just wish they would’ve had an ice machine and microwaves inside the hotel . It would’ve been 5 stars if they had microwaves and ice. Also the receptionist attitude wasn’t the best. I didn’t feel very welcomed and seemed like she was just trying to rush me away.
Reviewed on Feb 26, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥418,182, price is now ￥320,874 per person
￥320,874
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Always the best place to stay downtown. Central to everything with a great staff. Highly recommend!
Reviewed on Feb 25, 2026
The Emily Hotel
Downtown Chicago
Price was ￥374,962, price is now ￥292,332 per person
￥292,332
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Hotel is great. A lovely boutique venue. Friendly, professional and courteous staff made us feel very welcome.
Reviewed on Feb 24, 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 ￥12,488 per night from Mar 1 to Mar 2
￥12,488
￥13,986 total
Mar 1 - Mar 2
includes taxes & fees
8/10 Very Good! (1,003 reviews)
It was great for a cheap hotel! Good hot tub and pool. Good free waffles and breakfast. Good rooms. The only thing was the tv was broken in a few rooms but that was just because a football team recently came through. They kindly let us switch rooms so we had a working Tv :)
Reviewed on Feb 24, 2026
Spring House Inn
303 N Mineral Springs Rd Chesterton IN
Fully refundableReserve now, pay when you stay
The price is ￥13,876 per night from Feb 27 to Feb 28
￥13,876
￥16,321 total
Feb 27 - Feb 28
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
This is a super cute Inn nestled in some woods. We were greeted by a family of deer right outside our room. Room was clean, quiet and affordable! Felt more like a State Park Inn.
Reviewed on Feb 16, 2026
Waterbird Lakeside Inn
556 Indian Boundary Road Chesterton IN
Fully refundableReserve now, pay when you stay
8.2/10 Very Good! (1,000 reviews)
Things were okay.
Reviewed on Feb 20, 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.
Discover the most popular places to visit in Chesterton
Indiana Dunes State Park
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.
