Cheap Flights to Chicago: Chicago Flight Deals

View €319 flight on Wed, 21 Jan 2026Opens in a new window

Popular airlines to Chicago

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Cheap round-trip flights to Chicago

Prices were available within the past 7 days and start at €319 for one-way flights and €355 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Sat, 7 Feb - Sun, 15 Feb
DUB
Dublin
ORD
Chicago
€355 Return, found 2 hours ago
€355
Return
found 2 hours ago
Select TAP Portugal flight, departing Sat, 7 Feb from Dublin to Chicago, returning Sun, 15 Feb, priced at €355 found 2 hours ago
Icelandair
Fri, 12 Dec - Sun, 14 Dec
DUB
Dublin
ORD
Chicago
€388 Return, found 1 day ago
€388
Return
found 1 day ago
Select Icelandair flight, departing Fri, 12 Dec from Dublin to Chicago, returning Sun, 14 Dec, priced at €388 found 1 day ago
Scandinavian Airlines
Sat, 24 Jan - Mon, 2 Feb
DUB
Dublin
ORD
Chicago
€390 Return, just found
€390
Return
just found
Select Scandinavian Airlines flight, departing Sat, 24 Jan from Dublin to Chicago, returning Mon, 2 Feb, priced at €390 just found
American Airlines
Sat, 24 Jan - Mon, 2 Feb
DUB
Dublin
ORD
Chicago
€397 Return, just found
€397
Return
just found
Select American Airlines flight, departing Sat, 24 Jan from Dublin to Chicago, returning Mon, 2 Feb, priced at €397 just found
Aer Lingus
Fri, 5 Dec - Mon, 15 Dec
DUB
Dublin
ORD
Chicago
€415 Return, found 1 day ago
€415
Return
found 1 day ago
Select Aer Lingus flight, departing Fri, 5 Dec from Dublin to Chicago, returning Mon, 15 Dec, priced at €415 found 1 day ago

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

August is typically the cheapest month to fly

From €74 - €317 per traveller.

Frequently asked questions

What is the name of Chicago's airport?
Chicago has more than one airport, but most travellers touch down at O'Hare Intl. Airport (ORD).
How far is O'Hare Intl. Airport (ORD) from central Chicago?
The journey from O'Hare Intl. Airport (ORD) to downtown Chicago is fairly long. You'll need to travel 26 kilometres before you can check in to your city hotel.
What airport is best to fly into Chicago?
A flight to Chicago means hopping off the plane at O'Hare Airport or Chicago Airport. The first is 26 kilometres away from downtown. The second is 14 kilometres away.
How many airlines fly to Chicago?
There are a total of 51 airlines connecting Chicago with 237 airports globally.
Which airlines fly to Chicago?
Chicago receives the highest number of flights from United Airlines, American Airlines and Delta with United Airlines being the number one choice of airline. New York is the most popular city for passengers to jet off from.
How many nonstop flights are there to Chicago?
With roughly 7,564 nonstop flights running every week, you'll be hitting the runway in Chicago before you can ask, "Are we there yet?"
Where are the most popular flights to Chicago departing from?
The most popular flights to Chicago set off from New York, Washington and Dallas airports.
How long is the flight to Chicago Airport?
If it's New York you're leaving behind, you'll be in the air for around 2 hours and 44 minutes before you arrive in Chicago. Terminal to terminal from Washington generally takes 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Chicago?
Don't leave booking your flight to Chicago until the last minute. That's one trick seasoned travellers use to get the best prices. Booking well in advance means more choices and cheaper flights. Don't stop there, however. Do some research and see if there is more than one airport at your destination. Fares often differ depending on which airport you go for. Don't forget to compare fares across air carriers too. Finally, another easy way to save a few dollars is be ready to book at a moment's notice. If you stumble on a good bargain, don't hold off — grab it while you can.
Do you have any tips for my flight to Chicago?
Depending on where you're coming from, your trip to Chicago could be simple and straightforward or it could go on forever. We've put together some handy tips that will help you start your next unforgettable escape on the right foot. What to pack in your hand luggage:

  • It's simple — first, pack your passport, travel documents, wallet and daily medications. Next, you'll need some in-flight entertainment to while away the hours. A thrilling book and a laptop filled with your favourite shows are some wonderful options. If you intend to take a quick nap, a neck pillow and a pair of earplugs will also be useful. Finally, leave some space for a few toiletry items to ensure you touchdown feeling fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of shampoo and hair gel in your checked luggage. Any gels or liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp or pointed objects, like a Swiss Army knife, and dangerous products which are explosive or flammable, such as spray paint, flares and fireworks, are also restricted.

What to wear on a flight:

  • Choose comfort over style. Prepare for changes in temperature by donning layers, and opt for flat, enclosed shoes like sneakers.
  • Most of us have heard about deep vein thrombosis (DVT), a blood clot condition caused by long periods of inactivity. To reduce your risk on board, stay hydrated, consider wearing compression socks and move your lower limbs often.

How to get through airport security fast when flying to Chicago?
The secret is to be well prepared before you arrive at airport security. That way, you'll be boarding that plane to Chicago in a flash. Follow these helpful tips and get your holiday off to a fantastic start:

  • First things first. Your passport and boarding pass will need to be shown to airport security personnel. Keep them at hand so you don't have to dig around for them.
  • Your belt, jacket, keys and other small items, like your headphones, will need to go through the X-ray machine. Make the whole process faster by removing them as your turn draws near.
  • For just a few moments, you'll need to unplug from the digital world. Your phone, laptop and any other electronic gadgets will need to go through the scanner.
  • Remove all gels and liquids from your hand luggage. They often need to be sent through the X-ray machine separately. Each product 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.
  • The right choice of footwear can save you several minutes. Boots are often required to be removed and X-rayed separately. Slip-on shoes usually aren't.
  • Airlines will not allow any sharp objects to come on board with you. If you must bring these kinds of items, check them in.

Book with confidence

Expedia.ie is an online travel company that specialises in securing the best prices for flights to Chicago. 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 Chicago. 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 Chicago, or are just on the lookout for the best flights to Chicago, 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 Chicago 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

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
€101

Trending flights to Chicago

Prices were available within the past 7 days and start at €319 for one-way flights and €355 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

TAP Portugal
Sat, 7 Feb - Sun, 15 Feb
DUB
Dublin
ORD
Chicago
€355 Return, found 2 hours ago
€355
Return
found 2 hours ago
Select TAP Portugal flight, departing Sat, 7 Feb from Dublin to Chicago, returning Sun, 15 Feb, priced at €355 found 2 hours ago

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