Cheap Flights to Winnetka , IL from CA $152

View CA $152 flight on Sat, Oct. 25, 2025Opens 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 $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Nov. 28 - Sun, Nov. 30
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 16 hours ago
CA $244
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Fri, Nov. 28 from Toronto to Chicago, returning Sun, Nov. 30, priced at CA $244 found 16 hours ago
United
Sat, Nov. 1 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, just found
CA $244
Roundtrip
just found
Select United flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $244 just found
Porter Airlines
Tue, Aug. 12 - Wed, Sep. 3
YTZ
Toronto
MDW
Chicago
CA $249 Roundtrip, found 6 days ago
CA $249
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Tue, Aug. 12 from Toronto to Chicago, returning Wed, Sep. 3, priced at CA $249 found 6 days ago
WestJet
Sat, Oct. 11 - Mon, Oct. 27
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 15 hours ago
CA $256
Roundtrip
found 15 hours ago
Select WestJet flight, departing Sat, Oct. 11 from Calgary to Chicago, returning Mon, Oct. 27, priced at CA $256 found 15 hours ago
American Airlines
Fri, Oct. 24 - Mon, Oct. 27
YYC
Calgary
ORD
Chicago
CA $256 Roundtrip, found 15 hours ago
CA $256
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Fri, Oct. 24 from Calgary to Chicago, returning Mon, Oct. 27, priced at CA $256 found 15 hours ago

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 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!

Frequently asked questions

What is the name of Winnetka's airport?
Most travellers prefer to fly into O'Hare Intl. Airport (ORD) when visiting the happening city of Winnetka.
How far is O'Hare Airport from central Winnetka?
If you're staying in central Winnetka, it's a good idea to organize how you'll get into the city before you arrive. The downtown area is 21 kilometres from O'Hare Airport.
What airport is best to fly into Winnetka?
A flight to Winnetka means hitting the runway at either O'Hare Airport or Chicago Airport. The first is 21 kilometres away from the centre of the city. The second is 32 kilometres away.
How many airlines fly to Winnetka?
Winnetka is serviced by 51 airlines from at least 237 airports across the globe.
Which airlines fly to Winnetka?
United Airlines, American Airlines and Delta fly the most frequently to Winnetka. The highest number of flights come from New York, with United Airlines offering the most services on this route.
How many nonstop flights are there to Winnetka?
Flying to somewhere new is much simpler when there aren't any stopovers to slow you down. If you're off to Winnetka, the awesome news is that there are roughly 7,564 nonstop flights operating every week.
Where are the most popular flights to Winnetka departing from?
The most popular flights to Winnetka set off from New York, Washington and Dallas airports.
How long is the flight to Winnetka Airport?
If you're heading to Winnetka from New York, you're looking at a flight duration of 2 hours and 44 minutes. Those departing from Washington should expect to be airborne for around 2 hours and 15 minutes. From Dallas it's around 2 hours and 18 minutes away.
How to book the cheapest flight to Winnetka?
We've all come across those travellers who somehow score incredibly cheap plane tickets whenever they fly. Would you like to know how to do it for your Winnetka vacation? Don't wait until the last minute to lock in your flight. Another excellent way to get a bargain is to shop around. If where you're headed has several airports, look into the cost of flying into a less busy terminal. Last of all, another easy way to save a few dollars is be ready to book fast. If you stumble on a terrific deal, don't hesitate --- snap it up while you can.
Do you have any tips for my flight to Winnetka?
Depending on where you're coming from, your trip to Winnetka could be a piece of cake or it could drag on forever. Below are some handy tips that will help you start your next big adventure on the right foot. What to pack in your hand luggage:

  • First, pack your passport, travel docs, cash and daily medications. Next, you'll need some extra in-flight entertainment to while away the hours. A thrilling novel and a phone filled with your favourite shows are some wonderful options. If you hope to take a quick nap, a comfy neck pillow and some earplugs will also come in handy. Finally, leave some space for a few toiletry items to ensure you arrive feeling fresh and ready to go.

Do not pack the following items in your hand luggage:

  • Double-check that you don't have sharp objects (like a knife or scissors) lurking in one of the compartments of your hand luggage. Other banned items include explosive or flammable goods, such as aerosol cans and bleach, and liquids and gels in containers larger than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Your top priority is to feel as comfortable as possible. Pick shoes that are easy to pull on and off, dress in loose, natural fibers and don't forget to take a jacket in case you get cold in the cabin.
  • Deep vein thrombosis (DVT), a blood clot condition caused by lengthy periods of inactivity, can be a risk on long-haul flights. Try to wander 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 Winnetka?
The simple answer is --- be prepared. We've compiled some top tips for a speedy trip through security. Look out Winnetka, here you come:

  • Be sure to keep your ID and travel documents someplace easily accessible. They're the first things you'll be asked for by security.
  • Time to strip down. Well kind of. Your jacket, belt, keys and other contents of your pockets, like your earphones, will need to go on a tray through the X-ray machine. Make your life easier by removing them before your turn arrives.
  • For just a few moments, you'll have to unplug from technology. Your laptop, phone and any other electronics must also be sent through the scanner.
  • Any liquids or gels, such as perfume or hand cream, that you want to bring 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 possibility that you'll need to remove your shoes for scanning, so wearing slip-on shoes is always a wise idea.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp objects like a pocket knife or tools, put them in your checked luggage. They won't be allowed in the cabin.

Flights to Winnetka information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $244

Trending flights to Winnetka

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $244 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Nov. 28 - Sun, Nov. 30
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 16 hours ago
CA $244
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Fri, Nov. 28 from Toronto to Chicago, returning Sun, Nov. 30, priced at CA $244 found 16 hours ago
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