Darien Vacations from ￥253,402

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The Latest Darien Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
May 21 - May 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,665 reviews)
Really enjoyed our stay at the Arlo. Easy to get to a lot of different restaurants, museums, theaters and shopping. The staff was very friendly and helpful. The room was clean and comfortable. Would stay again!

Reviewed on Apr 19, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
May 21 - May 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.8/10 Excellent! (1,988 reviews)
One of the cleanest and friendliest hotels I’ve ever stayed in. Highly recommend, everything is walkable.

Reviewed on Apr 19, 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
May 21 - May 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,013 reviews)
This is easily one of the most gorgeous hotels I’ve ever stayed in. The interior design is next level. It is spotless and luxe, and the staff is phenomenal. Can’t wait to go back!

Reviewed on Apr 18, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
May 21 - May 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Good property if you don’t need housekeeping ($100 daily) and you don’t mind having to pull up to a closed garage and make a phone call for them to open it for you as there’s no codes. Other than being very inconvenient and having a front desk, that’s designed to accommodate the residence and therefore lacks the traditional pleasantries of a hospitality hotel, the rooms themselves are nice. But forget about service from this property! It’s a residential property that has a hotel feature that is minimally staffed, and Lax the traditional hotel amenities

Reviewed on Apr 16, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
May 21 - May 27
found 24 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Rooms were clean and spacious. Disappointed at the bar staff, not very engaging.

Reviewed on Apr 6, 2025

Find the Best Darien Vacation Packages

Darien Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,607 per night from Apr 21 to Apr 22
￥22,607
￥26,538 total
includes taxes & fees
Apr 21 - Apr 22
8.2/10 Very Good! (3,906 reviews)
"Very nice, affordable hotel option for families, with large rooms, abundant breakfast, daily room cleaning, nice staff, great location. We liked the included breakfast (only bad thing is that it stops at 9:30), the free daily happy hour with variety of snacks. Location is great, with plenty of dining ..."

Reviewed on Apr 19, 2025

Embassy Suites by Hilton Chicago Downtown River North
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is ￥17,915 per night from May 4 to May 5
￥17,915
￥21,031 total
includes taxes & fees
May 4 - May 5
8.8/10 Excellent! (1,010 reviews)
"Nice hotel with convenient locations"

Reviewed on Apr 17, 2025

Crowne Plaza Chicago West Loop by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥14,230 per night from Apr 21 to Apr 22
￥14,230
￥16,704 total
includes taxes & fees
Apr 21 - Apr 22
7.8/10 Good! (8,683 reviews)
"A good location for Auditorium performances."

Reviewed on Apr 18, 2025

Congress Plaza Hotel
See all 3,370 properties in Darien
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.

Frequently asked questions

How much does a Darien vacation package cost?
You can snap up a vacation package to this destination from ￥253,402 on Expedia. However, how much your vacation to Darien costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Darien?
If you’d like to snag a cheap Darien vacation package, consider traveling in April, July and November. You’ll typically find lower prices on hotels and airfares during these months — ideal for budget-conscious travelers.
How many days is enough for Darien?
The ideal length for your Darien vacation depends on what you’d like to see. Usually, a handful of days to a week will give you plenty of time to check out all the top attractions and discover some hidden treasures along the way.
How to find the best Darien package deals?
Use Expedia’s handy filters to help you find some of the best Darien package deals. When you begin your search, just set your maximum budget and then order the results by “Price: low to high.” If you want to save, plan your trip for midweek, or look for Darien package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it’s usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Darien vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You’ll usually get a better deal than booking each component individually. And you’ll still have the flexibility to create a personalized Darien vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Darien?
Secure incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Darien vacation.
How to plan a trip to Darien?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Darien.
  2. Set your budget: Factor in expenses like food, flights and transportation when calculating how much to save for your trip to Darien. Then, choose a property that fits your budget, whether that’s an affordable option or a more upscale getaway.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you want to get to in Darien. Then, estimate how long you’ll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a personalized Darien vacation package.

Discover the most popular places to visit in Darien

Wrigley Field featuring cbd, a sporting event and a city

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.

Wrigley Field
Magnificent Mile - River North showing night scenes, a city and signage

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.

Michigan Avenue
Six Flags Great America featuring rides

Six Flags Great America

4.5/5(347 reviews)

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Darien

Flyover in Chicago

Flyover in Chicago

￥5,588
per adult
98% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

￥7,166
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

￥6,538
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Darien
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.