
Midlothian Vacations from ¥236,814
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The Latest Midlothian Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥265,722, price is now ¥236,814 per person
¥236,814
per person
Apr 2 - Apr 4
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The staff was super friendly and accommodating. The rooms were immaculately clean, and the spa was amazing
Reviewed on Jan 13, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥382,354, price is now ¥306,076 per person
¥306,076
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
When we arrived at check in time, we were informed that our room was not ready but that we could upgrade at a discounted additional cost to a suite. At first, we didn't want to do that and decided to wait. The host provided complimentary round of drinks and meal for the wait. We decided to upgrade and I'm so glad that we did. The room was incredible and the service, from concierge, staff and valets, here is top notch. We ordered the Waldorf salad and Waldorf chocolate chip cookies because you have to if you stay here. Loved this place and will definitely return.
Reviewed on Jan 5, 2026


Viceroy Chicago
Downtown Chicago
Price was ¥286,474, price is now ¥255,829 per person
¥255,829
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
Staff is always excellent. Our favorite stay in the Chicago area.
Reviewed on Jan 9, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ¥288,804, price is now ¥258,341 per person
¥258,341
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Friendly and welcoming staff, extremely helpful valet, beautiful room, comfortable beds, and a warm ambiance. We genuinely enjoyed our stay here. We were only in town for one night, but we would have easily been comfortable here for a longer stay. Walking distance to many popular places, and the hotel itself was in a safe area. (Whenever I travel without my husband, that is of particular concern, so it was appreciated.) The next time we're in town for a show, we will absolutely stay at the Kimpton Gray again.
Reviewed on Jan 11, 2026
Find the Best Midlothian Vacation Packages
Midlothian Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥14,349 per night from Jan 19 to Jan 20
¥14,349
¥16,844 total
Jan 19 - Jan 20
includes taxes & fees
8/10 Very Good! (9,772 reviews)
Room was noce
Reviewed on Jan 15, 2026

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥20,616 per night from Feb 1 to Feb 2
¥20,616
¥28,841 total
Feb 1 - Feb 2
includes taxes & fees
8.4/10 Very Good! (2,538 reviews)
Great staff, good location .
Reviewed on Jan 14, 2026

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥17,504 per night from Jan 25 to Jan 26
¥17,504
¥20,548 total
Jan 25 - Jan 26
includes taxes & fees
8.4/10 Very Good! (5,548 reviews)
.
Reviewed on Jan 16, 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 Midlothian

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Midlothian

Skydeck - Willis Tower Admission
¥6,889
per adult
100% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,845
per adult
88% of travellers recommend
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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.

