Chicago Vacations from ￥370,524
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ￥421,994, price is now ￥370,524 per person
￥370,524
per person
Mar 20 - Mar 27
found 9 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
Clean rooms. Quiet.
Reviewed on Jan 2, 2026
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥487,101, price is now ￥409,684 per person
￥409,684
per person
Mar 20 - Mar 27
found 9 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
We noticed the plumbing was very noisy in adjoining rooms. Woke us up at 4 am
Reviewed on Jan 5, 2026
L7 Chicago by LOTTE
Downtown Chicago
Price was ￥445,857, price is now ￥393,881 per person
￥393,881
per person
Mar 20 - Mar 27
found 9 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
9.6/10 Exceptional! (3,227 reviews)
Room was in good condition. Mattress was firm enough to give me a good night sleep.
Reviewed on Jan 6, 2026
Great Wolf Lodge Illinois
Price was ￥595,514, price is now ￥529,826 per person
￥529,826
per person
Mar 20 - Mar 27
found 9 hours ago
Roundtrip non-stop flight included
Nagoya (NGO) to Chicago (ORD)
8.6/10 Excellent! (1,001 reviews)
The staff is great, Diviana at front desk was super nice and polite. She explained everything. Thank you for your hospitality.
Reviewed on Jan 1, 2026
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,997 per night from Jan 13 to Jan 14
￥13,997
￥16,431 total
Jan 13 - Jan 14
includes taxes & fees
8.8/10 Excellent! (3,660 reviews)
We had a wonderful stay at the Hilton. The staff was exceptionally helpful in providing any information we neede. A shout out to Latis and Christian, who were extremely friendly, always created us with a smile and we’re eager to help. We will definitely stay here again.
Reviewed on Jan 6, 2026
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥22,344 per night from Jan 12 to Jan 13
￥22,344
￥30,145 total
Jan 12 - Jan 13
includes taxes & fees
8.4/10 Very Good! (2,226 reviews)
Room was very clean and staff was great
Reviewed on Jan 6, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,702 per night from Jan 13 to Jan 14
￥21,702
￥30,072 total
Jan 13 - Jan 14
includes taxes & fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...
Reviewed on Jan 5, 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 Chicago
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.
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.
What to do in Chicago
Skydeck - Willis Tower Admission
￥6,889
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,845
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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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.
