
Countryside Vacations from ¥206,246
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The Latest Countryside Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Arlo Chicago
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,749 reviews)
Check in and check out we’re easy. The staff were all friendly and helpful. The room was as advertised with a great view.
Reviewed on Jun 15, 2025


The Peninsula Chicago
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,004 reviews)
The customer service was top notch, everyone went above and beyond to make my stay an exceptional experience!! 5 Stars All around!!
Reviewed on Jun 10, 2025


Level Chicago – Old Town
Downtown Chicago
per person
Sep 1 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (319 reviews)
I had no idea how nice this property would be! I had a full one-bedroom apartment and amazing view and amenities. 10/10, would stay again!
Reviewed on Jun 1, 2025
Find the Best Countryside Vacation Packages
Countryside Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥23,316 per night from Jun 30 to Jul 1
¥23,316
¥27,372 total
Jun 30 - Jul 1
includes taxes & fees
8.4/10 Very Good! (4,234 reviews)
"I love everything about this hotel, especially the breakfast plus you have a happy hour. The only thing that I can say is that the bathroom needs to have a vent because if you shut the door for a long time, it smells like mildew, so I had to keep making sure the door stays open but other than that, ..."
Reviewed on Jun 18, 2025

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ¥24,795 per night from Jul 6 to Jul 7
¥24,795
¥33,747 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (1,891 reviews)
"Hotel is very clean with friendly staff. The pool was a highlight for the kids! Convenient location."
Reviewed on Jun 19, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥19,597 per night from Jul 6 to Jul 7
¥19,597
¥23,005 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (2,313 reviews)
"Valet parking too expensive."
Reviewed on Jun 18, 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 Countryside

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.

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.
What to do in Countryside

Wendella's 90-min Chicago River Architecture Tour
¥6,507
per adult
94% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,499
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.