
Medinah Vacations from ¥183,198
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Medinah Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥428,510, price is now ¥344,590 per person
¥344,590
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The room was boring thought it would be cleaner updated for the price best part was the view
Reviewed on Jan 24, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥299,862, price is now ¥244,036 per person
¥244,036
per person
Apr 15 - Apr 18
just found
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service
Reviewed on Jan 20, 2026

Find the Best Medinah Vacation Packages
Medinah Hotel Deals

Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥30,514 per night from Feb 14 to Feb 15
¥30,514
¥35,820 total
Feb 14 - Feb 15
includes taxes & fees
8.2/10 Very Good! (2,199 reviews)
Great stay
Reviewed on Jan 23, 2026

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ¥21,043 per night from Jan 28 to Jan 29
¥21,043
¥23,984 total
Jan 28 - Jan 29
includes taxes & fees
8.8/10 Excellent! (2,348 reviews)
Didn’t have breakfast
Reviewed on Jan 22, 2026

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ¥16,349 per night from Jan 28 to Jan 29
¥16,349
¥18,636 total
Jan 28 - Jan 29
includes taxes & fees
8.6/10 Excellent! (2,717 reviews)
Staff was great. Breakfast buffet was perfect for us, and the location worked well for connecting with our flight.
Reviewed on Jan 22, 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 Medinah

Michigan Avenue
4.5/5(332 reviews)
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.

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Medinah

Chicago: Navy Pier Centennial Wheel Ticket
¥3,883
per adult
88% of travellers recommend

Chicago Blackhawks Ice Hockey Game at United Center
¥10,567
per adult
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


