Darien Holidays

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Top Flight + Hotel Deals in Darien

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 17 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on 21 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 17 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Самый лучший отель в чикаго

Reviewed on 28 Jul 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 17 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.4/10 Exceptional! (3,357 reviews)
The room was luxurious and pleasant. Location perfect for reaching any activity whether on business or personal visit. Love it!! ❤️💃

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 17 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
6 Sept - 11 Sept
found 17 hours ago
Return flight included
Las Vegas (LAS) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
Quick and easy check in. Parking in their private garage was breeze. Plenty of space, mostly empty, and our vehicle could stay in the garage until 2:00 PM the next day. Beautiful 1 BR condo. Full kitchen, beautiful views of the city on the balcony and from the living room, and very clean space overall. Need your key card for just about everything (pool, lounge, some of the outdoor bathrooms, elevators, etc.).

Reviewed on 27 Jul 2025

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 €180 per night from 4 Aug to 5 Aug
€180
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (9,025 reviews)
"There are areas of the property outside that need some tlc. The hallways are outdated in decor but the room was clean and comfortable. The reception area was very pretty. The staff was courteous and friendly. The hotel itself has a good location walkable to the Soldier Field which we were in town ..."

Reviewed on 29 Jul 2025

Congress Plaza Hotel
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
The price is €152 per night from 24 Aug to 25 Aug
€152
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,322 reviews)
"The location was great and close to a lot of good restaurants and bars. Also walkable to the downtown area, but with a bus stop 5 minutes away."

Reviewed on 29 Jul 2025

Crowne Plaza Chicago West Loop by IHG
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 €167 per night from 24 Aug to 25 Aug
€167
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (4,589 reviews)
"First time in the city and I was happy with the location of our lodging. I am NOT...happy about needing some toilet paper for our bathroom, and we asked the cleaning lady for some and she just told me, "I dont have any!!!" All the while....cleaning and refreahing a room two doors down from us. That ..."

Reviewed on 29 Jul 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 3,752 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.

Popular places to visit

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

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

Michigan Avenue

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
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Darien

River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

€39
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Darien

Frequently asked questions

How much does a Darien holiday package cost?
You can snap up a holiday package to this destination from €720 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.