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Cheap Flights to Darien , IL from CA $192

View CA $192 flight on Sun, Sep 6, 2026Opens in a new window

Popular airlines to Darien

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How much is the cheapest flight to Darien?

Prices were available within the past 7 days and start at CA $192 for one-way flights and CA $322 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, Sep 25 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $322 Roundtrip, found 2 hours ago
CA $322
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Fri, Sep 25 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $322 found 2 hours ago
Air Canada
Tue, Sep 8 - Sun, Sep 13
YTZ
Toronto
ORD
Chicago
CA $341 Roundtrip, just found
CA $341
Roundtrip
just found
Select Air Canada flight, departing Tue, Sep 8 from Toronto to Chicago, returning Sun, Sep 13, priced at CA $341 just found
Air Transat
Sun, Sep 6 - Tue, Sep 15
YTZ
Toronto
MDW
Chicago
CA $353 Roundtrip, just found
CA $353
Roundtrip
just found
Select Air Transat flight, departing Sun, Sep 6 from Toronto to Chicago, returning Tue, Sep 15, priced at CA $353 just found
American Airlines
Thu, Sep 3 - Wed, Sep 9
YYZ
Toronto
ORD
Chicago
CA $355 Roundtrip, just found
CA $355
Roundtrip
just found
Select American Airlines flight, departing Thu, Sep 3 from Toronto to Chicago, returning Wed, Sep 9, priced at CA $355 just found
Delta
Mon, Dec 14 - Tue, Dec 15
YYZ
Toronto
ORD
Chicago
CA $361 Roundtrip, just found
CA $361
Roundtrip
just found
Select Delta flight, departing Mon, Dec 14 from Toronto to Chicago, returning Tue, Dec 15, priced at CA $361 just found

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

May is typically the cheapest month to fly

From CA $129 - CA $398 per traveller.

Frequently asked questions

What is the name of Darien's airport?
Many visitors prefer to fly into O'Hare Intl. Airport (ORD) when visiting the buzzing city of Darien.
How far is O'Hare Airport from central Darien?
O'Hare Airport is 26 kilometres from downtown Darien, so be prepared for a decent commute into the city centre.
What airport is best to fly into Darien?
If you're planning on jumping on a plane to Darien, you'll probably arrive at ORD (26 kilometres from downtown). Chicago Airport (19 kilometres from downtown) is the other main airport here.
How many airlines fly to Darien?
There are 51 airlines that fly into Darien from 237 airports across the globe.
Which airlines fly to Darien?
Most often, travellers choose to fly with United Airlines, American Airlines and Delta when going to Darien. The largest number of these flights depart from New York, with United Airlines operating this route the most frequently.
How many nonstop flights are there to Darien?
Flying to a new place is much more straightforward when there aren't any stopovers to worry about. If you're heading to Darien, the awesome news is that there are around 7,564 nonstop flights operating every week.
Where are the most popular flights to Darien departing from?
Flights to Darien departing from New York, Washington and Dallas airports are the most sought after.
How long is the flight to Darien Airport?
If it's New York you're departing, you'll be in the sky for around 2 hours and 44 minutes before you arrive in Darien. Tarmac to tarmac from Washington generally takes 2 hours and 15 minutes and from Dallas, the flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Darien?
We all know those lucky travellers who manage to grab extremely cheap airfares whenever they fly. Would you like to know how to do it for your Darien vacation? Don't wait until the last minute to lock in your flight. Also, do some online research and compare your options. If your destination has a few airports, you may be able to score an excellent price by flying into a less busy terminal. Lastly, another easy way to save some money is be ready to book fast. If you stumble on an amazing bargain, don't hold off — snap it up while you can.
Do you have any tips for my flight to Darien?
Wherever you're jetting in from, flying can be a pleasant experience if you've prepared well. We've compiled a list of handy travel tips that will help get your Darien escape started on the right foot. What to pack in your hand luggage:

  • Air travel can be easy if you carry the right stuff. First things first, you'll need basic toiletries, such as a toothbrush and hairbrush, a fresh set of clothes and a good novel. Secondly, find a spot in your bag for your electronic devices, chargers, your medications and perhaps a blow-up neck pillow too. Lastly, and most importantly, be sure to bring your passport, travel docs and some money.

Do not pack the following items in your hand luggage:

  • While the list of restricted items can differ between airlines, the general rule to follow is avoid carrying anything flammable, sharp or explosive. This includes tools, metal cutlery, aerosol cans and flares. Sports equipment like golf clubs, and objects that could injure passengers, such as pepper spray and guns, won't be allowed on board either.

What to wear on a flight:

  • You'll want to choose comfort over style. Prepare for temperature changes by wearing layers, and opt for closed-toe, flat shoes like sneakers.
  • Deep vein thrombosis (DVT), a blood clotting condition caused by lengthy periods of inactivity, can be a risk on long-haul flights. Try to walk around the cabin or do some simple exercises in your seat to promote better circulation.

How to get through airport security fast when flying to Darien?
A little pre-planning before your flight can make your getaway to Darien a piece of cake. Below you'll find some top tips for a swift journey through security:

  • Airport security personnel first need to see that you have a valid passport and travel documents before anything else. Have them close by, ready for inspection.
  • Next up is the X-ray machine. Empty your pockets and remove anything metal that is likely to set off the alarm. This includes items like headphones or earphones, as well as your coat or jacket. They'll all need to go on the X-ray conveyor belt.
  • Your electronic gadgets like phones and laptops will also have to go through the machine to be scanned. No need to worry though, you'll be back online in no time.
  • 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 inside a quart-size (one litre), clear zip-close bag.
  • Choosing your footwear wisely can save you several valuable minutes. Boots are often required to be removed and X-rayed separately. Lightweight sneakers are usually not.
  • Sharp items like knives are prohibited in the cabin. They'll be seized at security, so pack them in your checked suitcase.

Book with confidence

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!

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $321

Trending flights to Darien

Prices were available within the past 7 days and start at CA $192 for one-way flights and CA $322 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Fri, Sep 25 - Mon, Sep 28
YTZ
Toronto
MDW
Chicago
CA $322 Roundtrip, found 2 hours ago
CA $322
Roundtrip
found 2 hours ago
Select Porter Airlines flight, departing Fri, Sep 25 from Toronto to Chicago, returning Mon, Sep 28, priced at CA $322 found 2 hours ago

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