Darien Vacations from ￥240,559
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The Latest Darien Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥521,912, price is now ￥392,400 per person
￥392,400
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Our stay was absolutely excellent! The room was spotless and stylish, but what really stood out was the rooftop — breathtaking views, great ambiance, and the perfect spot to unwind. The concierge team was phenomenal — attentive, knowledgeable, and made every recommendation feel personalized. From check-in to check-out, everything felt seamless and top-tier. Truly a 5-star experience worth repeating!
Reviewed on Oct 28, 2025
The Emily Hotel
Downtown Chicago
Price was ￥310,491, price is now ￥251,834 per person
￥251,834
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Excellent stay. The hotel staff is very courteous and helpful, and the location is great!
Reviewed on Oct 28, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥456,542, price is now ￥371,712 per person
￥371,712
per person
Nov 30 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,011 reviews)
Our guests that are not from Chicago there should be some sort of a quick tips handout that gives an overview of the events that are taking place over the next week popular restaurants things that are within walking distance of the hotel
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥338,290, price is now ￥283,958 per person
￥283,958
per person
Jan 17 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Beautiful hotel, great view and clean, the only thing that was missing in the room is a Bible. The front desk was very friendly and helpful, but the bell hop and door attendants aren’t as friendly and lacking of customer service.
Reviewed on Oct 29, 2025
Find the Best Darien Vacation Packages
Darien Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥25,967 per night from Nov 2 to Nov 3
￥25,967
￥30,482 total
Nov 2 - Nov 3
includes taxes & fees
7.8/10 Good! (9,629 reviews)
Affordable, beautiful, easy to parking, close to everything. The only think I didn’t like was the fire alarm in my room was on for almost 30 minutes, the lights in my bathroom while I was showering got off and something touch me that was a very strange feeling and the bathroom starting to smell like ...
Reviewed on Oct 30, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥19,334 per night from Nov 16 to Nov 17
￥19,334
￥22,696 total
Nov 16 - Nov 17
includes taxes & fees
8.4/10 Very Good! (5,168 reviews)
The best hotel and best location best breakfast
Reviewed on Oct 29, 2025
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥17,387 per night from Nov 19 to Nov 20
￥17,387
￥20,410 total
Nov 19 - Nov 20
includes taxes & fees
9.2/10 Wonderful! (4,024 reviews)
Good stay, good location, excellent helpful staff. Emergency vehicles sirens could be heard at times.
Reviewed on Oct 30, 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
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 Darien
Skydeck - Willis Tower Admission
￥6,612
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,691
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.
