Darien Vacations from ￥189,824
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Darien Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥246,540, price is now ￥189,824 per person
￥189,824
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly.
Reviewed on Dec 6, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥307,991, price is now ￥211,934 per person
￥211,934
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Pablo at reception was the most amazing! Amazing service, beautiful view, convenient location. Excellent hotel. Only thing for improvement would be better lighting in the bathroom.
Reviewed on Dec 14, 2025
Chicago luxury home suites
Downtown Chicago
Save 100% on your flight
Price was ￥564,895, price is now ￥393,365 per person
￥393,365
per person
Feb 20 - Feb 25
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
The Peninsula Chicago
Downtown Chicago
Price was ￥367,895, price is now ￥260,594 per person
￥260,594
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
One of the best, if not the best we have ever stayed at. Staff were exceptional including Osama who made us welcome from the moment we arrived.
Outstanding!!
Reviewed on Dec 15, 2025
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥351,432, price is now ￥249,102 per person
￥249,102
per person
Feb 20 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Absolutely fantastic hotel great service, you couldn’t ask for more.
Reviewed on Dec 3, 2025
Find the Best Darien Vacation Packages
Darien Hotel Deals
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (2,127 reviews)
This hotel was great. In a perfect spot for walking the city and taking in all the sights. We had 3 of us in our group and we got the 1br with 2 queens beds and a pullout couch and it was perfect. The bar was fun and everyone we met in the staff were so friendly and helpful with suggestions on places ...
Reviewed on Dec 16, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥16,905 per night from Dec 30 to Dec 31
￥16,905
￥23,718 total
Dec 30 - Dec 31
includes taxes & fees
8.4/10 Very Good! (2,142 reviews)
Everything was great!
Reviewed on Dec 16, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥11,595 per night from Dec 29 to Dec 30
￥11,595
￥13,613 total
Dec 29 - Dec 30
includes taxes & fees
8.6/10 Excellent! (1,989 reviews)
Very clean and the staff was wonderful!
Reviewed on Dec 13, 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 Darien
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.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Darien
Wendella's 90-min Chicago River Architecture Tour
￥6,310
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,827
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
