Cheap Flights to Winnetka: Winnetka Flight Deals

View €249 flight on Tue, 11 Nov 2025Opens in a new window

Popular airlines to Winnetka

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Cheap round-trip flights to Winnetka

Prices were available within the past 7 days and start at €249 for one-way flights and €344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Icelandair
Tue, 17 Feb - Tue, 24 Feb
DUB
Dublin
ORD
Chicago
€344 Return, found 6 days ago
€344
Return
found 6 days ago
Select Icelandair flight, departing Tue, 17 Feb from Dublin to Chicago, returning Tue, 24 Feb, priced at €344 found 6 days ago
TAP Portugal
Tue, 11 Nov - Fri, 28 Nov
DUB
Dublin
ORD
Chicago
€354 Return, found 1 hour ago
€354
Return
found 1 hour ago
Select TAP Portugal flight, departing Tue, 11 Nov from Dublin to Chicago, returning Fri, 28 Nov, priced at €354 found 1 hour ago
Aer Lingus
Sat, 21 Feb - Sat, 28 Feb
DUB
Dublin
ORD
Chicago
€404 Return, found 1 day ago
€404
Return
found 1 day ago
Select Aer Lingus flight, departing Sat, 21 Feb from Dublin to Chicago, returning Sat, 28 Feb, priced at €404 found 1 day ago
Air France
Fri, 21 Nov - Tue, 25 Nov
DUB
Dublin
MDW
Chicago
€408 Return, found 6 days ago
€408
Return
found 6 days ago
Select Air France flight, departing Fri, 21 Nov from Dublin to Chicago, returning Tue, 25 Nov, priced at €408 found 6 days ago
United
Sat, 18 Oct - Fri, 24 Oct
SNN
Shannon
ORD
Chicago
€431 Return, found 6 days ago
€431
Return
found 6 days ago
Select United flight, departing Sat, 18 Oct from Shannon to Chicago, returning Fri, 24 Oct, priced at €431 found 6 days ago

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

July is typically the cheapest month to fly

From €66 - €224 per traveller.

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 further 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

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Winnetka. With Expedia you get highly specialised services, combining the best of technology, in-depth knowledge and the best connections in order to offer great deals to Winnetka. Expedia shares your passion for travel and has built the best online travel service that promotes and encourages travel. Whether you are looking for cheap flights to Winnetka, or are just on the lookout for the best flights to Winnetka, you are sure to find the best deals with Expedia.ie.

"One of the many benefits of booking your flights through Expedia is that we are one of the world’s largest online travel agency, which means we use our collective experience and work tirelessly to bring you the best prices. With Expedia you get a user-friendly internet experience and a dedicated customer support service that ensures that everything goes smoothly. The goal of Expedia is to offer premium services at the lowest price, all at one single place. If you wish to save even more try combing a hotel in Winnetka to your flight and create a personalised low cost city break or holiday to your favourite destination. Book early and you could save even more!

If you have an Expedia.ie itinerary number and have a question or concern about your travel plans you can call us on (01) 524 5005 from 8am - 10pm Monday to Friday, and 9am - 10pm at weekends and an Expedia agent will help you.

Travel information

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
€344

Trending flights to Winnetka

Prices were available within the past 7 days and start at €249 for one-way flights and €344 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Icelandair
Tue, 17 Feb - Tue, 24 Feb
DUB
Dublin
ORD
Chicago
€344 Return, found 6 days ago
€344
Return
found 6 days ago
Select Icelandair flight, departing Tue, 17 Feb from Dublin to Chicago, returning Tue, 24 Feb, priced at €344 found 6 days ago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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