Oak Brook Vacations from ￥305,446
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The Latest Oak Brook Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥530,808, price is now ￥411,160 per person
￥411,160
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,872 reviews)
We had an amazing time, we absolutely loved our stay
Reviewed on May 29, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥419,722, price is now ￥342,909 per person
￥342,909
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
I enjoyed our stay at LondonHouse Chicago, Curio Collection by Hilton. Staff members were friendly and helpful! Housekeeping staff were friendly and on point with cleaning! My next visit to Chicago, I plan on staying there.
Reviewed on May 27, 2026
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥390,095, price is now ￥326,618 per person
￥326,618
per person
Aug 10 - Aug 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,163 reviews)
We really enjoyed our stay at this beautiful hotel! The hotel was extremely clean and the rooms were large and well designed. The amenities were top notch. The front desk staff were extremely knowledgeable and helpful. You can walk to any of the top attractions from this hotel and we put on 9 miles a day walking the city. Highly recommend this hotel for your stay in the Windy City!
Reviewed on May 29, 2026
Find the Best Oak Brook Vacation Packages
Oak Brook Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,737 per night from Jun 29 to Jun 30
￥20,737
￥24,653 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"
Reviewed on May 29, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥30,104 per night from Jun 30 to Jul 1
￥30,104
￥40,329 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,288 reviews)
"Staff was super nice and attentive."
Reviewed on May 29, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is ￥24,209 per night from Jun 28 to Jun 29
￥24,209
￥28,783 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,487 reviews)
"rooftop"
Reviewed on May 29, 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 Oak Brook
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.
Michigan Avenue
4.5/5(336 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 Oak Brook
Skydeck - Willis Tower Admission
￥6,904
per adult
96% 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.
