Cheap Flights to Winfield , IL from CA $152

View CA $152 flight on Thu, Oct. 9, 2025Opens in a new window

Popular airlines to Winfield

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 30% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

How much is the cheapest flight to Winfield?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Thu, Oct. 9 - Wed, Oct. 15
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 6 hours ago
CA $243
Roundtrip
found 6 hours ago
Select Air Canada flight, departing Thu, Oct. 9 from Toronto to Chicago, returning Wed, Oct. 15, priced at CA $243 found 6 hours ago
United
Fri, Nov. 28 - Sun, Nov. 30
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Fri, Nov. 28 from Toronto to Chicago, returning Sun, Nov. 30, priced at CA $244 just found
Porter Airlines
Tue, Aug. 12 - Wed, Sep. 3
YTZ
Toronto
MDW
Chicago
CA $249 Roundtrip, found 4 days ago
CA $249
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Aug. 12 from Toronto to Chicago, returning Wed, Sep. 3, priced at CA $249 found 4 days ago
American Airlines
Thu, Oct. 23 - Tue, Oct. 28
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, just found
CA $256
Roundtrip
just found
Select American Airlines flight, departing Thu, Oct. 23 from Calgary to Chicago, returning Tue, Oct. 28, priced at CA $256 just found
WestJet
Thu, Oct. 23 - Sun, Oct. 26
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, just found
CA $256
Roundtrip
just found
Select WestJet flight, departing Thu, Oct. 23 from Calgary to Chicago, returning Sun, Oct. 26, priced at CA $256 just found

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

June is typically the cheapest month to fly

From CA $105 - CA $339 per traveller.

Graph displaying average flight prices per month

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

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 Winfield 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 Winfield.

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

Frequently asked questions

What is the name of Winfield's airport?
The majority of visitors prefer to fly into O'Hare Intl. Airport (ORD) when visiting the bustling city of Winfield.
How far is ORD from central Winfield?
O'Hare Airport is 24 kilometres from central Winfield, so be prepared for a bit of a commute into the centre.
What airport is best to fly into Winfield?
Flying to Winfield means hitting the runway at ORD or Chicago Airport. The first is 24 kilometres away from the centre of the city. The second is 32 kilometres away.
How many airlines fly to Winfield?
There are 51 airlines that service Winfield from 237 airports around the world.
Which airlines fly to Winfield?
United Airlines, American Airlines and Delta are the most frequent fliers to Winfield. The majority of these flights arrive here from New York, with United Airlines offering the most services on this route.
How many nonstop flights are there to Winfield?
With approximately 7,564 nonstop flights each week, you'll be hitting the tarmac in Winfield before you can say, "Are we there yet?"
Where are the most popular flights to Winfield departing from?
Travellers often depart from New York, Washington and Dallas airports when heading to Winfield.
How long is the flight to Winfield Airport?
Where you depart from determines how much of the in-flight entertainment you'll get to enjoy. From New York to Winfield, the average flight time is 2 hours and 44 minutes. From Washington it's around 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Winfield?
Don't leave booking your flight to Winfield until the last moment. That's one move well-versed jet-setters use to get the best deals. Booking well in advance means more choices and cheaper flights. Also, look around online and compare your options. If your destination has multiple airports, you may be able to nab a great price by flying into a smaller terminal. Finally, another easy way to save some cash is be ready to book fast. If you spot a fantastic bargain, don't hold off --- grab it while you can.
Do you have any tips for my flight to Winfield?
If you're poorly prepared, air travel can be overwhelming. But don't hit the panic button just yet. Follow these handy tips and enjoy a stress-free start to your getaway in Winfield. What to pack in your hand luggage:

  • The secret to having a hassle-free flight experience is to plan ahead. So, let's start with the essentials: passport, official ID, credit cards and any vital medications. Next, bring items that'll help keep you busy, like your laptop or a few magazines. It's also wise to pack your chargers, a neck pillow and a pair of headphones. Last but not least, don't forget to chuck in toiletry items like a toothbrush, lip balm and a fresh change of clothes.

Do not pack the following items in your hand luggage:

  • Check carefully that you don't have sharp or pointed objects lurking in your hand luggage. Other banned items include flammable or explosive goods, such as fuel and fireworks, and liquids and gels in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by donning layers, and pick flat, closed-toe shoes like slip-ons.
  • Caused by sustained periods of immobility, deep vein thrombosis (DVT) is a blood clotting condition that can affect passengers during long-distance flights. Reduce the risks by staying hydrated, keeping your legs and feet moving and wearing compression socks to help your circulation.

How to get through airport security fast when flying to Winfield?
It's all about being prepared. We've compiled some handy tips and tricks for a hassle-free trip through security. Look out Winfield, here you come:

  • Be sure to keep your passport and travel documents within easy reach. They're the first things you'll be asked for by airport security.
  • Next up is the X-ray machine. Empty your pockets and remove anything metal that is likely to beep. This includes items like earphones or headphones, as well as bulky coats or jackets. They'll need to be placed on the conveyor belt for screening.
  • Your electronic gadgets like phones and laptops will also need to go on a tray for inspection. Don't worry though, you'll be back online before you know it.
  • Remove liquids and gels from your hand luggage. They usually need to be sent through the X-ray scanner separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a single quart-size (one litre), clear zip-close bag.
  • Lightweight sneakers are a great footwear choice as you're less likely to have to remove them when going through security. Hiking boots and other heavy shoes are often subjected to additional screening.
  • Pocket knives and other sharp items can't be taken on board. They'll be seized at security, so put them in your checked suitcase.

Flights to Winfield information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $243

Trending flights to Winfield

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Oct. 8 - Wed, Oct. 8
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, found 4 hours ago
CA $243
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Wed, Oct. 8 from Toronto to Chicago, returning Wed, Oct. 8, priced at CA $243 found 4 hours ago
*Available to Expedia members.