Cheap Flights to Winnetka , IL from CA $178

View CA $178 flight on Tue, Oct 6, 2026Opens in a new window

Popular airlines to Winnetka

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How much is the cheapest flight to Winnetka?

Prices were available within the past 7 days and start at CA $178 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
Tue, Sep 22 - Sat, Sep 26
YUL
Montreal
ORD
Chicago
CA $282 Roundtrip, found 8 hours ago
CA $282
Roundtrip
found 8 hours ago
Select Air Canada flight, departing Tue, Sep 22 from Montreal to Chicago, returning Sat, Sep 26, priced at CA $282 found 8 hours ago
Porter Airlines
Tue, Jun 16 - Sat, Jun 20
YTZ
Toronto
MDW
Chicago
CA $342 Roundtrip, just found
CA $342
Roundtrip
just found
Select Porter Airlines flight, departing Tue, Jun 16 from Toronto to Chicago, returning Sat, Jun 20, priced at CA $342 just found
American Airlines
Wed, Jun 17 - Fri, Jun 19
YYZ
Toronto
ORD
Chicago
CA $355 Roundtrip, just found
CA $355
Roundtrip
just found
Select American Airlines flight, departing Wed, Jun 17 from Toronto to Chicago, returning Fri, Jun 19, priced at CA $355 just found
United
Sun, Jun 7 - Sat, Jun 13
YYZ
Toronto
ORD
Chicago
CA $355 Roundtrip, just found
CA $355
Roundtrip
just found
Select United flight, departing Sun, Jun 7 from Toronto to Chicago, returning Sat, Jun 13, priced at CA $355 just found
Delta
Tue, Jun 9 - Sat, Jun 20
YYZ
Toronto
MDW
Chicago
CA $362 Roundtrip, found 2 days ago
CA $362
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 9 from Toronto to Chicago, returning Sat, Jun 20, priced at CA $362 found 2 days ago

Alternative airports near Winnetka

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city centre is 27 minutes. Flights from CA $502
ORD
O'Hare Intl.
Average driving time to city centre27 min
Flights from CA $502
Select flight to Midway Intl. MDW. Cheapest option available. Average driving time to city centre is 38 minutes. Flights from CA $387
MDW
Midway Intl.
Cheapest
Average driving time to city centre38 min
Flights from CA $387

Frequently asked questions

What is the name of Winnetka's airport?
O'Hare Intl. Airport (ORD) is the main airport in Winnetka.
How far is O'Hare Intl. Airport (ORD) from central Winnetka?
It's 21 kilometres from O'Hare Intl. Airport (ORD) to downtown Winnetka. Make things easier by working out the best way of getting from the airport to the city centre before you touchdown.
What airport is best to fly into Winnetka?
There are two main airports that service Winnetka. ORD is around 21 kilometres from the downtown area, while Midway Airport is approximately 32 kilometres away. As soon as you find a good price and work out where you're staying, you'll have a better idea of which one to head to.
How many airlines fly to Winnetka?
There are a total of 51 airlines connecting Winnetka to 237 airports around the world.
Which airlines fly to Winnetka?
In general, travellers choose to fly with United Airlines, American Airlines and Delta when heading to Winnetka. The biggest proportion of these flights come in from New York, with United Airlines servicing this route the most.
How many nonstop flights are there to Winnetka?
Flying to someplace new is much more straightforward when there aren't any stopovers to slow you down. If you're heading to Winnetka, the fantastic news is that there are approximately 7,564 direct flights each week.
Where are the most popular flights to Winnetka departing from?
The most popular flights to Winnetka leave from New York, Washington and Dallas airports.
How long is the flight to Winnetka Airport?
If it's New York you're departing, you'll be in the sky for around 2 hours and 44 minutes before you touchdown in Winnetka. Tarmac to tarmac from Washington typically takes 2 hours and 15 minutes and from Dallas, it's 2 hours and 18 minutes.
How to book the cheapest flight to Winnetka?
Don't leave locking in your flight to Winnetka until the last minute. That's one move savvy jet-setters use to get the best deals. Booking ahead means more options and more affordable flights. Also, look around online and compare your options. If your destination has multiple airports, you may be able to nab an excellent deal by flying into one a little farther out. Lastly, be ready to book quickly if you find a real bargain. It might not be available for too long. With a bit of knowledge and some good fortune, the perfect fare can be yours.
Do you have any tips for my flight to Winnetka?
Depending on where you're coming from, your flight to Winnetka could be as easy as pie or it could drag on forever. We've compiled some useful travel tips that will help you start your unforgettable escape on the right foot. What to pack in your hand luggage:

  • First and foremost, put in your passport, travel docs, bank cards and medications. Next, you'll want some entertainment to while away the time. A juicy novel and a phone crammed with your favourite movies are some wonderful options. If you hope to catch more than just forty winks, a quality neck pillow and a pair of noise-cancelling headphones will also be useful. Finally, find room for a toothbrush and some deodorant so you'll arrive at your destination looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • While the list of banned items can differ between air carriers, the general rule to follow is avoid carrying anything sharp, flammable or explosive. This includes box cutters, razor blades, spray paint and flares. Sporting equipment like hockey sticks, and objects that could harm other people, such as pepper spray and firearms, 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 donning layers, and pick flat, slightly roomy shoes like slip-ons.
  • It's likely you've heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To lower your risk on board, stay hydrated, consider wearing compression socks and do gentle foot and leg exercises in your seat.

How to get through airport security fast when flying to Winnetka?
Being prepared before you arrive at the airport can make your getaway to Winnetka a piece of cake. Read through our useful tips for a speedy journey past security:

  • First things first. Your boarding pass and passport will need to be shown to airport security personnel. Keep them handy so you don't have to dig around for them.
  • The X-ray machine comes next. Empty your pockets and remove anything metal that is likely to set off the scanner's alarm. This includes items like headphones or earphones, as well as heavy coats or jackets. They'll all need to go on the X-ray conveyor belt.
  • All electronic gadgets, including your tablet and phone, are also required to be scanned separately.
  • Any gels or liquids, such as lip balm or cologne, that you want to take on board need to be in containers no greater than 3.4 ounces (100 millilitres). Also, everything must fit inside a quart-size (one litre), zip-lock bag.
  • There's a good chance you'll be asked to take your shoes off for scanning, so wearing lightweight sneakers is always a smart idea.
  • Airlines won't allow any pocket knives or other sharp items in the cabin. If you need to bring these kinds of items, put them in your checked luggage.

Book with confidence

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

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 Winnetka 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 Winnetka.

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

Travel information

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

Trending flights to Winnetka

Prices were available within the past 7 days and start at CA $178 for one-way flights and CA $282 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Wed, Sep 16 - Wed, Sep 16
YTZ
Toronto
ORD
Chicago
CA $340 Roundtrip, found 21 hours ago
CA $340
Roundtrip
found 21 hours ago
Select Porter Airlines flight, departing Wed, Sep 16 from Toronto to Chicago, returning Wed, Sep 16, priced at CA $340 found 21 hours ago

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