
Chicago Vacations from ¥178,628
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ¥239,045, price is now ¥178,628 per person
¥178,628
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city
Reviewed on Nov 26, 2025

Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ¥596,650, price is now ¥424,452 per person
¥424,452
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop 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

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥339,130, price is now ¥242,749 per person
¥242,749
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It's always perfection at the Trump. King suite with Lake view is the ultimate
Reviewed on Dec 2, 2025

Level Chicago – Old Town
Downtown Chicago
Price was ¥275,290, price is now ¥202,281 per person
¥202,281
per person
Jan 28 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views.
Reviewed on Dec 3, 2025
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

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is ¥14,689 per night from Dec 18 to Dec 19
¥14,689
¥17,243 total
Dec 18 - Dec 19
includes taxes & fees
8.4/10 Very Good! (5,341 reviews)
Great place. Cant beat it or the staff
Reviewed on Dec 2, 2025

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥12,976 per night from Dec 7 to Dec 8
¥12,976
¥15,232 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,420 reviews)
3 day business trip. Hotel is a great location to dow,town. Easy walk to great restaurants and stores
Reviewed on Dec 2, 2025

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥16,072 per night from Dec 28 to Dec 29
¥16,072
¥22,756 total
Dec 28 - Dec 29
includes taxes & fees
8.4/10 Very Good! (2,121 reviews)
W
Reviewed on Dec 2, 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 Chicago

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
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
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago

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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