
Trail Creek Vacations from ¥267,343
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The Latest Trail Creek Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥374,596, price is now ¥267,343 per person
¥267,343
per person
Mar 23 - Mar 30
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Cleanliness, exceptional customer service, and a complimentary upgrade made our stay outstanding! The way the buffet staff efficiently managed the line, guided guests to tables, and consistently kept the food fresh—all while wearing genuine smiles—was truly impressive. Our room was spotless, modern, and well-stocked, exceeding our expectations. We will definitely be back!
Reviewed on Jan 11, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥517,344, price is now ¥361,336 per person
¥361,336
per person
Mar 23 - Mar 30
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Staff was excellent
Reviewed on Jan 13, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥382,283, price is now ¥286,916 per person
¥286,916
per person
Mar 23 - Mar 30
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
I stayed 5 nights total, 4 nights in a two BR, 1 bath with a balcony and the last night in a one BR. The 2BR was great. It faced East, received a lot of sunlight, was clean, modern and the bed was very comfortable. The gym had what I needed too. actually liked sleeping with the sound of the el nearby because I used to live in the area. I did not give it 5 stars because the walls are super thin. Someone had a party next to me and it was impossible to sleep hearing voices straight through the walls. Being a newer building, I don’t think the best quality appliances or fixtures were chosen. My ice machine wasn’t working and the heat/fan only worked in certain areas in the 2BR. Additional lighting should be added. The 1BR shower fixtures and drain needed some attention. That said, Mihajlo and the front desk staff were very helpful and attentive and helped me with whatever I needed. The 1BR seemed more like a studio to m. I’d prefer to book directly through Level, but it was a better price with Expedia. I still thought it was pricey but I was overall happy with my stay.
Reviewed on Jan 12, 2026


The Peninsula Chicago
Downtown Chicago
Price was ¥536,808, price is now ¥407,372 per person
¥407,372
per person
Mar 23 - Mar 30
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on Jan 11, 2026
Trail Creek Hotel Deals

Blue Chip Casino Hotel and Spa
777 Blue Chip Drive Michigan City IN
Fully refundableReserve now, pay when you stay
The price is ¥15,031 per night from Jan 14 to Jan 15
¥15,031
¥19,487 total
Jan 14 - Jan 15
includes taxes & fees
8.2/10 Very Good! (1,902 reviews)
Even though it was a room that has not been updated yet, it was just fine Enjoyable trip.
Reviewed on Jan 7, 2026

Four Winds Casino Resort – New Buffalo
11111 Wilson Road New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is ¥13,286 per night from Jan 14 to Jan 15
¥13,286
¥15,413 total
Jan 14 - Jan 15
includes taxes & fees
9.2/10 Wonderful! (1,676 reviews)
Nice hotel, clean rooms and friendly staff
Reviewed on Jan 12, 2026

Baymont by Wyndham New Buffalo
18800 Harbor Country Drive New Buffalo MI
Fully refundableReserve now, pay when you stay
The price is ¥10,065 per night from Jan 22 to Jan 23
¥10,065
¥10,870 total
Jan 22 - Jan 23
includes taxes & fees
6.8/10 (1,018 reviews)
Great stay
Reviewed on Dec 27, 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.
Frequently asked questions
Discover the most popular places to visit in Trail Creek
Lighthouse Place Premium Outlets
You can browse for the perfect souvenirs at Lighthouse Place Premium Outlets during your stay in Michigan City. Visit the area's casinos or amble around its beautiful beaches.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.