Darien Holidays

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Top hotels in Darien

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 €118 per night from 26 Dec to 27 Dec
€118
includes taxes & fees
26 Dec - 27 Dec
7.8/10 Good! (8,279 reviews)
"This is a very old property which is part of it's charm. Water pressure in the shower was very limited. Accomodations are simple. Really liked new vinyl flooring in room with throw rug. Much better than carpeting. I will return."

Reviewed on 21 Dec 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €105 per night from 22 Jan to 23 Jan
€105
includes taxes & fees
22 Jan - 23 Jan 2025
8.6/10 Excellent! (3,626 reviews)
"Having to park my car 4 blocks away"

Reviewed on 22 Dec 2024

River Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
The price is €127 per night from 7 Jan to 8 Jan
€127
includes taxes & fees
7 Jan - 8 Jan 2025
8.6/10 Excellent! (1,286 reviews)
"I loved the pool, it was very big and spaceous and the water temp was perfect. The room it self was also nice. would def recommend coming back."

Reviewed on 22 Dec 2024

Holiday Inn Chicago Dwtn Wolf Point, an IHG Hotel
See all 3,378 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 holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday package, consider travelling in April, July and November. You’ll typically find lower prices on hotels and airfares during these months — ideal for budget-conscious travellers.
How many days is enough for Darien?
The ideal length for your Darien holiday 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 holiday package as early as possible.
Is it cheaper to book a Darien holiday as a package?
Expedia holiday 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 personalised Darien holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 holiday.
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 personalised Darien holiday package.

Popular places to visit

Magnificent Mile - River North showing street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home 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
Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

What to do in Darien

Flyover in Chicago

Flyover in Chicago

€36
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

€46
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

€42
per adult
88% 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.