Countryside Vacations from ￥461,740
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- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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The Latest Countryside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
￥475,652
per person
Oct 8 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Fantastic breakfast, great location, great room. The rooftop terrace was amazing, but we wishes we had known to make a reservation to be able to enjoy a drink there.
Reviewed on Aug 26, 2026
Swissotel - Chicago
Downtown Chicago
￥471,246
per person
Nov 15 - Nov 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Pros: Location is excellent. View was excellent. They upgraded my room from the 4th floor to the 28th floor at no extra cost. Cleaned when I requested.
Cons: Staff was a bit snooty snooty hoity toity. Didn't know I had to pay for parking so that cost more than I budgeted for, it was also an unnecessary hassle to do due to poor internet connection. Confusing amenity fees that I thought I was properly taking advantage of but toward the end felt was taking advantage of me to extract more money. I requested some items be brought up to our room only for staff to tell me I had to come down to the lobby myself to grab them.
Ultimately I can summarize the experience easily as its not worth what I paid for. Also no pool but thats more on me for not checking for that ahead of time.
Reviewed on Aug 26, 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
￥16,989
￥20,200 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very Good! (10,322 reviews)
"Staff at the front desk were friendly and helpful during check-in and throughout our stay. Unfortunately, the room itself made it very difficult to actually rest. We were on the 12th floor, and street noise came through all night as if the windows weren't sealed at all — there was essentially no ..."
Reviewed on Aug 27, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥21,337
￥25,369 total
Aug 31 - Sep 1
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
￥38,752
￥45,489 total
Sep 18 - Sep 19
includes taxes & fees
8.4/10 Very Good! (2,446 reviews)
"Very convenient, helpful staff"
Reviewed on Aug 26, 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.
What to do in Countryside
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
per adult
88% of travellers recommend
Frequently asked questions
How much does a Countryside vacation package cost?
Offering great value package deals from ￥461,740 on Expedia, you'll be thrilled with how little a vacation to Countryside costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Countryside?
If you're hoping to score a cheap Countryside vacation package, consider visiting in January, February and April. You'll generally find lower rates on hotels and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Countryside?
Usually, a handful of days is enough to check out the top attractions during your Countryside vacation. But if you'd like to have time to rest or go on day trips, consider extending your itinerary.
How to find the best Countryside package deals?
Finding a cheap Countryside package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Countryside package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Countryside vacation as a package?
An Expedia vacation package could land you great savings when compared to booking stays and flights separately. Better still, you can customize your Countryside escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Countryside?
Land incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Countryside trip.
How to plan a trip to Countryside?
- Choose your dates: What you plan to do in Countryside and your preferred season can help you decide when to go.
- Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will probably be the largest expense during your trip to Countryside.
- Work out your trip length: Think about how much time you'd like to spend discovering Countryside. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Countryside vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
