Oak Park Vacations from ￥233,222
Book a Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Oak Park Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was ￥310,180, price is now ￥233,222 per person
￥233,222
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Clean room cool staff enjoyed my stay will come stay again.
Reviewed on Nov 30, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥400,088, price is now ￥287,144 per person
￥287,144
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on Dec 1, 2025
Chicago luxury home suites
Downtown Chicago
Price was ￥624,610, price is now ￥452,412 per person
￥452,412
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.
Reviewed on Nov 26, 2025
The Emily Hotel
Downtown Chicago
Price was ￥322,576, price is now ￥239,918 per person
￥239,918
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on Nov 26, 2025
Find the Best Oak Park Vacation Packages
Oak Park 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 ￥14,369 per night from Dec 7 to Dec 8
￥14,369
￥16,866 total
Dec 7 - Dec 8
includes taxes & fees
8.4/10 Very Good! (5,334 reviews)
The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ...
Reviewed on Nov 30, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,009 per night from Dec 7 to Dec 8
￥13,009
￥15,270 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,423 reviews)
Very good. Great location.
Reviewed on Nov 30, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,649 per night from Dec 28 to Dec 29
￥16,649
￥23,449 total
Dec 28 - Dec 29
includes taxes & fees
8.4/10 Very Good! (2,112 reviews)
Absolutely gorgeous! This hotel offers everything you need and want. Excellent food, amenities and the spa is the best part. We had a mother and daughter weekend with massage's, it was what we hoped for and more.
Reviewed on Nov 29, 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.
Discover the most popular places to visit in Oak Park
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.
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.
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 Oak Park
Wendella's 90-min Chicago River Architecture Tour
￥7,083
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,866
per adult
84% 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.
