Addison Vacations from ￥203,685
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Addison Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥350,452, price is now ￥290,705 per person
￥290,705
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb
Reviewed on Nov 10, 2025
Pendry Chicago
Downtown Chicago
Price was ￥247,007, price is now ￥206,792 per person
￥206,792
per person
Dec 25 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Rooms are lovely, bar / restaurant is top notch. Love staying at the pendry!
Reviewed on Nov 10, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥345,035, price is now ￥293,264 per person
￥293,264
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥320,001, price is now ￥275,657 per person
￥275,657
per person
Jan 1 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Clean! Staff friendly and a great location.
Reviewed on Nov 11, 2025
Find the Best Addison Vacation Packages
Addison Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is ￥15,587 per night from Dec 9 to Dec 10
￥15,587
￥18,298 total
Dec 9 - Dec 10
includes taxes & fees
8.4/10 Very Good! (5,208 reviews)
Friendly staff, well appointed room, needed more pillows and received very quickly.
Reviewed on Nov 8, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,518 per night from Dec 7 to Dec 8
￥15,518
￥18,217 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,258 reviews)
Room was terrific; staff, very helpful. All in all a great trip, and I’ll definitely revisit this property.
Reviewed on Nov 10, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥15,833 per night from Nov 12 to Nov 13
￥15,833
￥18,585 total
Nov 12 - Nov 13
includes taxes & fees
8/10 Very Good! (9,545 reviews)
It was fine in general. Location was great but view was not perfect just fine
Reviewed on Nov 9, 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 Addison
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 Addison
Skydeck - Willis Tower Admission
￥6,717
per adult
96% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,749
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
