
Countryside Vacations from ¥308,086
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ¥85,000 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 Countryside Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ¥351,959, price is now ¥308,086 per person
¥308,086
per person
Jun 10 - Jun 13
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.4/10 Very Good! (1,882 reviews)
Clean rooms, small rooms, small elevators. Friendly and helpful staff.
Reviewed on Apr 21, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥417,041, price is now ¥333,923 per person
¥333,923
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,914 reviews)
Great staff, very attentive to needs, very helpful
Reviewed on Apr 24, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥448,358, price is now ¥372,178 per person
¥372,178
per person
Jun 10 - Jun 13
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Great staff, facilities, esp the fitness & spa
Reviewed on Apr 23, 2026

Pendry Chicago
Downtown Chicago
Price was ¥408,956, price is now ¥341,230 per person
¥341,230
per person
Jun 10 - Jun 13
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,137 reviews)
Great hotel! Very central location, helpful staff. The speak easy was a great surprise
Reviewed on Apr 20, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥402,686, price is now ¥336,398 per person
¥336,398
per person
Jun 10 - Jun 13
found 22 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,458 reviews)
No restaurant or available food after 10pm.
Reviewed on Apr 21, 2026
Find the Best Countryside Vacation Packages
Countryside Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥18,379 per night from Apr 26 to Apr 27
¥18,379
¥21,577 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,133 reviews)
wifi wouldn’t connect, when we called the front desk to ask (I had work I needed to do, and specifically checked before booking that the room included wifi) was met with attitude to “just connect” even though the wifi network wasn’t visible or available. also, you have no control over the temperature ...
Reviewed on Apr 24, 2026

River Hotel
75 East Wacker Drive Chicago IL
The price is ¥18,831 per night from May 26 to May 27
¥18,831
¥22,390 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,123 reviews)
Wonderful and helpful sstaff. Excellent location
Reviewed on Apr 24, 2026

Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥13,764 per night from Apr 29 to Apr 30
¥13,764
¥21,032 total
Apr 29 - Apr 30
includes taxes & fees
8.2/10 Very Good! (2,635 reviews)
The staff were extremely impressed and helpful. Help me with restaurant choices, where to go for tours. Only thing I regretted was not packing the proper clothes for the chance of weather. It was my personal birthday present to me and I did enjoyed myself.
Reviewed on Apr 24, 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 Countryside

Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier
4.5/5(4,925 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Countryside

Skydeck - Willis Tower Admission
¥7,012
per adult
96% of travellers recommend
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.


