Cheap Flights to Darien , IL from CA $158

View CA $158 flight on Mon, Nov. 10, 2025Opens in a new window

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How much is the cheapest flight to Darien?

Prices were available within the past 7 days and start at CA $158 for one-way flights and CA $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Nov. 10 - Sat, Nov. 15
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 3 hours ago
CA $245
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Mon, Nov. 10 from Toronto to Chicago, returning Sat, Nov. 15, priced at CA $245 found 3 hours ago
United
Tue, Nov. 18 - Tue, Nov. 25
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 1 hour ago
CA $245
Roundtrip
found 1 hour ago
Select United flight, departing Tue, Nov. 18 from Toronto to Chicago, returning Tue, Nov. 25, priced at CA $245 found 1 hour ago
WestJet
Thu, Oct. 16 - Thu, Oct. 23
YYC
Calgary
ORD
Chicago
CA $250 Roundtrip, found 2 days ago
CA $250
Roundtrip
found 2 days ago
Select WestJet flight, departing Thu, Oct. 16 from Calgary to Chicago, returning Thu, Oct. 23, priced at CA $250 found 2 days ago
American Airlines
Thu, Sep. 18 - Wed, Sep. 24
YYC
Calgary
ORD
Chicago
CA $257 Roundtrip, found 1 hour ago
CA $257
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Sep. 18 from Calgary to Chicago, returning Wed, Sep. 24, priced at CA $257 found 1 hour ago
Delta
Wed, Sep. 17 - Sat, Sep. 20
YUL
Montreal
MDW
Chicago
CA $296 Roundtrip, found 4 days ago
CA $296
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep. 17 from Montreal to Chicago, returning Sat, Sep. 20, priced at CA $296 found 4 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

June is typically the cheapest month to fly

From CA $106 - CA $344 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Darien. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Darien. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Darien.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Darien flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Darien.

Looking to save even more? Get additional savings by bundling your Darien flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Darien trip!

Frequently asked questions

What is the name of Darien's airport?
Darien has several airports, but most visitors touch down at O'Hare Intl. Airport (ORD).
How far is ORD from central Darien?
Long commutes don't have to be stressful if you plan ahead for them. Downtown Darien is 26 kilometres from ORD, so it's smart to know how to get to the city before you touchdown.
What airport is best to fly into Darien?
Travellers flying into Darien can choose to touchdown at two major airports. O'Hare Intl. Airport (ORD) is 26 kilometres away from the downtown streets. Chicago Airport is 19 kilometres away.
How many airlines fly to Darien?
There are 51 airlines connecting Darien with 237 airports across the globe.
Which airlines fly to Darien?
Darien receives the largest number of flights from United Airlines, American Airlines and Delta with United Airlines being the favourite choice of airline. New York is the most popular city for passengers to take off from.
How many nonstop flights are there to Darien?
With around 7,564 direct flights running every week, you'll be touching down in Darien before you can ask, "Are we there yet?"
Where are the most popular flights to Darien departing from?
Travellers frequently set off from New York, Washington and Dallas airports when heading to Darien.
How long is the flight to Darien Airport?
If it's New York you're departing, you'll be midair for around 2 hours and 44 minutes before you arrive in Darien. Tarmac to tarmac from Washington takes approximately 2 hours and 15 minutes and from Dallas, 2 hours and 18 minutes.
How to book the cheapest flight to Darien?
Don't leave booking your flight to Darien until the last moment. That's one trick seasoned travellers use to get the best deals. Booking ahead means more choices and cheaper flights. Another excellent way to nab a bargain is to compare all options. If your destination has a few airports, be sure to look into the cost of flying into a less busy terminal. And finally, remember that it's first in, best dressed. Familiarize yourself with airfare costs and have your credit card ready to secure your ticket as soon as you see an unbeatable bargain. The best deals don't last long.
Do you have any tips for my flight to Darien?
Depending on where you're coming from, your journey to Darien could be simple and straightforward or it could drag on forever. We've compiled some tips that will help you start your unforgettable escape on a positive note. What to pack in your hand luggage:

  • The secret to having a pain-free flight experience is to pack ahead. Start with the essentials: passport, travel docs, bank cards and medications. Next, bring on board items that'll help keep you occupied, like your laptop or a good read. It's also wise to pack your chargers, a quality neck pillow and a pair of earplugs. Finally, be sure to chuck in toiletries like a toothbrush, lip balm and a clean T-shirt.

Do not pack the following items in your hand luggage:

  • Make sure you don't have a sharp object lurking in one of the compartments of your hand luggage. Other restricted items include flammable or explosive substances, such as aerosol cans and bleach, and gels and liquids in containers larger than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • The aisles of a plane aren't the place for a fashion parade. Dress in comfortable layers and opt for shoes that are closed-toe, flat and easy to take on and off.
  • Caused by prolonged periods of inactivity, deep vein thrombosis (DVT) is a blood clotting condition that can affect passengers during long-haul flights. Lower your risks by drinking water, keeping your ankles and legs moving and wearing compression socks or tights.

How to get through airport security fast when flying to Darien?
It's all about being prepared. We've compiled some helpful hints for a stress-free trip through security. Watch out Darien, here you come:

  • Security personnel first need to know that you have a valid passport and boarding pass before anything else. Have them in your hand, ready for inspection.
  • Next up is the X-ray machine. Remove anything on you that is likely to set off the scanner's alarm. This includes things like earphones or headphones, as well as heavy jackets or coats. They'll all need to go on the X-ray conveyor belt.
  • For just a few moments, you'll have to unplug from the digital world. Your phone, laptop and any other electronic gadgets also need to go through the scanner.
  • Remove all liquids and gels from your carry-on luggage. They often need to be sent through the X-ray machine separately. Each item should be no larger than 3.4 ounces (100 millilitres) and everything must fit in a quart-size (one litre), clear zip-close bag.
  • Lightweight sneakers are a clever footwear choice as you're less likely to have to remove them when passing through security. Hiking boots and other heavy-style shoes are often subjected to additional screening.
  • Sharp items such as knives and scissors are prohibited in the cabin. They'll be confiscated at security, so pack them safely away in your checked bags.

Flights to Darien information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $245

Trending flights to Darien

Prices were available within the past 7 days and start at CA $158 for one-way flights and CA $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Mon, Nov. 10 - Sat, Nov. 15
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 3 hours ago
CA $245
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Mon, Nov. 10 from Toronto to Chicago, returning Sat, Nov. 15, priced at CA $245 found 3 hours ago
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