Cheap Flights to Woodstock , IL from CA $159

View CA $159 flight on Sun, Apr 26, 2026Opens in a new window

Popular airlines to Woodstock

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How much is the cheapest flight to Woodstock?

Prices were available within the past 7 days and start at CA $159 for one-way flights and CA $282 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Mar 25 - Mon, Mar 30
YUL
Montreal
ORD
Chicago
CA $282 Roundtrip, just found
CA $282
Roundtrip
just found
Select Air Canada flight, departing Wed, Mar 25 from Montreal to Chicago, returning Mon, Mar 30, priced at CA $282 just found
WestJet
Sun, Apr 26 - Mon, Apr 27
YXX
Abbotsford
ORD
Chicago
CA $290 Roundtrip, found 1 day ago
CA $290
Roundtrip
found 1 day ago
Select WestJet flight, departing Sun, Apr 26 from Abbotsford to Chicago, returning Mon, Apr 27, priced at CA $290 found 1 day ago
United
Sat, Apr 11 - Tue, Apr 21
YUL
Montreal
ORD
Chicago
CA $295 Roundtrip, found 3 days ago
CA $295
Roundtrip
found 3 days ago
Select United flight, departing Sat, Apr 11 from Montreal to Chicago, returning Tue, Apr 21, priced at CA $295 found 3 days ago
Delta
Wed, Apr 29 - Fri, May 1
YUL
Montreal
ORD
Chicago
CA $298 Roundtrip, found 1 day ago
CA $298
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Apr 29 from Montreal to Chicago, returning Fri, May 1, priced at CA $298 found 1 day ago
American Airlines
Sun, Apr 12 - Sat, Apr 18
YYZ
Toronto
ORD
Chicago
CA $300 Roundtrip, just found
CA $300
Roundtrip
just found
Select American Airlines flight, departing Sun, Apr 12 from Toronto to Chicago, returning Sat, Apr 18, priced at CA $300 just found

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

July is typically the cheapest month to fly

From CA $109 - CA $427 per traveller.

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Frequently asked questions

What is the name of Woodstock's airport?
Organize a flight to Woodstock and you'll be touching down at O'Hare Intl. Airport (ORD).
What airport is best to fly into Woodstock?
A flight to Woodstock means landing at O'Hare Intl. Airport (ORD). Get off the plane, gather your bags and you'll be 56 kilometres from the downtown area.
How many airlines fly to Woodstock?
There are a total of 49 airlines connecting Woodstock with 224 airports across the world.
Which airlines fly to Woodstock?
Most often, travellers opt to fly with United Airlines, American Airlines and Delta when heading off to Woodstock. The majority of these flights come from New York, with United Airlines operating this route the most.
How many nonstop flights are there to Woodstock?
With roughly 6,379 direct flights running each week, you'll be hitting the tarmac in Woodstock before you can ask, "Are we there yet?"
Where are the most popular flights to Woodstock departing from?
Flights to Woodstock departing from New York, Washington and Dallas airports are highly sought after.
How long is the flight to Woodstock Airport?
If you're going to Woodstock from New York, you're looking at a flight time of 2 hours and 48 minutes. Those departing from Washington should expect to be airborne for around 2 hours and 18 minutes. From Dallas it's approximately 2 hours and 23 minutes away.
How to book the cheapest flight to Woodstock?
Don't leave booking your flight to Woodstock until the last moment. That's one trick seasoned jet-setters use to get the best prices. Booking well in advance means more choices and cheaper flights. Another fantastic way to pick up the best price is to compare all options. If your destination has multiple airports, research the cost of flying into a smaller terminal. And finally, don't forget that the early bird catches the worm. Familiarize yourself with airfare costs and have your credit card ready to reserve your seat as soon as you spot an unbeatable bargain. The best deals never last long.
Do you have any tips for my flight to Woodstock?
If you're poorly prepared, travelling can be overwhelming. But there's no need to hit the panic button just yet. Follow these useful tips and enjoy a pain-free start to your vacation in Woodstock. What to pack in your hand luggage:

  • The secret to having a pain-free flight experience is to plan ahead. So, let's start with the essentials: passport, travel documents, cash and any vital medications. Next, take on board items that'll help pass the time, like some electronic gadgets or a good read. It's also wise to bring your chargers, a comfy neck pillow and a pair of earplugs. Last but not least, don't forget to pop in toiletries like a toothbrush, cleansing wipes and a spare change of clothes.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between air carriers, the general guide to follow is avoid carrying anything flammable, sharp or explosive. This includes things like screwdrivers, drills, aerosol cans and bleaching agents. Sports equipment like hockey sticks, and objects that could injure passengers, such as pepper spray and firearms, aren't allowed in the cabin either.

What to wear on a flight:

  • You'll want to go for comfort over style. Prepare for temperature changes by wearing layers, and pick easy-to-remove footwear like slip-ons.
  • Deep vein thrombosis (DVT) is a potential risk on long-haul flights. It's the result of blood clots forming due to poor circulation and inactivity, so do some gentle foot and leg exercises in your seat and consider wearing compression socks or tights.

How to get through airport security fast when flying to Woodstock?
Being organized before you get to the airport will make your trip to Woodstock a piece of cake. Check out our handy tips and tricks for a swift journey through security:

  • Airport security personnel first need to verify that you have a valid passport and boarding pass before anything else. Keep them within easy reach.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other items in your pocket, like your headphones, will need to go through the X-ray machine. Make your life easier by removing them before your turn arrives.
  • Your electronic devices like laptops and phones will also need to go on a tray to be scanned. Don't worry though, you'll be back online soon enough.
  • Want to bring along your favourite hand cream? No problem. As long as the volume is no greater than 3.4 ounces (100 millilitres) and it's stored in a clear zip-close bag, you're permitted to bring it with you in your carry-on bag.
  • Slip-on shoes are a great footwear choice as you're less likely to be required to remove them when going through security. Safety boots and heavier-style shoes are often subjected to additional screening.
  • Airlines will not allow any sharp objects in the cabin. If you need to bring these kinds of items, check them in.

Book with confidence

Expedia.ca gives you the best tools to secure great deals on flights to Woodstock. 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 Woodstock. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Woodstock.

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 Woodstock 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 Woodstock.

Looking to save even more? Get additional savings by bundling your Woodstock 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 Woodstock trip!

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $281

Trending flights to Woodstock

Prices were available within the past 7 days and start at CA $159 for one-way flights and CA $282 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Wed, Mar 25 - Mon, Mar 30
YUL
Montreal
ORD
Chicago
CA $282 Roundtrip, just found
CA $282
Roundtrip
just found
Select Air Canada flight, departing Wed, Mar 25 from Montreal to Chicago, returning Mon, Mar 30, priced at CA $282 just found

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