€304 Find Cheap Flights to Chicago – Compare and Save

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Everything you should know

Cheapest return fare
€397
Typical prices: €480-€658
Icelandair
Thu 18/2Sun 28/2
DUB - ORD • 1 stop
Cheapest direct flights
€466
Typical prices: €454-€639
Aer Lingus
Thu 11/2Sun 21/2
DUB - ORD • Direct
Top airlines
Most flights • 14 per week
Best reviews • 7.6 score
Airline reviews
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Top routes
Insights
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When to book
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 28% compared to booking last minute.
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When to travel
Cheapest • 28% price drop
Most popular
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Flight Deals

Cheap Flights to Chicago

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Thu, 18 Feb - Sun, 28 Feb
Icelandair Logo
11:30 - 17:20DUB  Dublin-ORD Chicago O'Hare Intl
11h 50m1 stop Reykjavik Keflavik Intl
Icelandair Logo
18:30 - 10:15ORD  Chicago O'Hare Intl-DUB Dublin
9h 45m1 stop Reykjavik Keflavik Intl
€397Icelandair
Thu, 11 Feb - Sun, 21 Feb
Icelandair Logo
11:30 - 17:20DUB  Dublin-ORD Chicago O'Hare Intl
11h 50m1 stop Reykjavik Keflavik Intl
Icelandair Logo
18:30 - 10:15ORD  Chicago O'Hare Intl-DUB Dublin
9h 45m1 stop Reykjavik Keflavik Intl
€397Icelandair
Sat, 26 Dec - Thu, 31 Dec
British Airways Logo
13:05 - 18:45DUB  Dublin-ORD Chicago O'Hare Intl
11h 40m1 stop London Heathrow
British Airways Logo
17:10 - 09:55ORD  Chicago O'Hare Intl-DUB Dublin
10h 45m1 stop London Heathrow
€446British Airways
Thu, 25 Feb - Sun, 7 Mar
British Airways Logo
13:05 - 18:45DUB  Dublin-ORD Chicago O'Hare Intl
11h 40m1 stop London Heathrow
British Airways Logo
17:10 - 09:55ORD  Chicago O'Hare Intl-DUB Dublin
10h 45m1 stop London Heathrow
€446British Airways
Mon, 26 Oct - Mon, 2 Nov
Finnair Logo
09:45 - 18:45DUB  Dublin-ORD Chicago O'Hare Intl
14h 00m1 stop Helsinki-Vantaa
Finnair Logo
12:02 - 07:10ORD  Chicago O'Hare Intl-DUB Dublin
13h 08m1 stop Dallas/Fort Worth
€458Finnair
Mon, 26 Oct - Mon, 2 Nov
Finnair Logo
09:45 - 18:45DUB  Dublin-ORD Chicago O'Hare Intl
14h 00m1 stop Helsinki-Vantaa
Finnair Logo
12:02 - 07:10ORD  Chicago O'Hare Intl-DUB Dublin
13h 08m1 stop Dallas/Fort Worth
€458Finnair
Thu, 11 Feb - Sun, 21 Feb
Aer Lingus Logo
16:40 - 19:15DUB  Dublin-ORD Chicago O'Hare Intl
8h 35mdirect
Aer Lingus Logo
21:00 - 10:25ORD  Chicago O'Hare Intl-DUB Dublin
7h 25mdirect
€466Aer Lingus
Fri, 26 Feb - Sun, 7 Mar
Aer Lingus Logo
16:40 - 19:15DUB  Dublin-ORD Chicago O'Hare Intl
8h 35mdirect
Aer Lingus Logo
15:55 - 05:15ORD  Chicago O'Hare Intl-DUB Dublin
7h 20mdirect
€466Aer Lingus
Sun, 21 Feb - Mon, 1 Mar
American Airlines Logo
11:30 - 22:30DUB  Dublin-ORD Chicago O'Hare Intl
17h 00m1 stop Philadelphia
American Airlines Logo
16:50 - 08:30ORD  Chicago O'Hare Intl-DUB Dublin
9h 40m1 stop Philadelphia
€483American Airlines
Sun, 14 Feb - Sat, 20 Feb
American Airlines Logo
11:30 - 17:34DUB  Dublin-ORD Chicago O'Hare Intl
12h 04m1 stop Philadelphia
American Airlines Logo
16:50 - 08:30ORD  Chicago O'Hare Intl-DUB Dublin
9h 40m1 stop Philadelphia
€483American Airlines
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends into flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Shannon, at €397 return. The most popular connection is from Dublin to Chicago, while KAYAK users have found return deals for as low as €397 in the last 5 days.

How much is a flight to Chicago?

A flight to Chicago costs €903 on average. The cheapest price found on KAYAK in the last 2 weeks cost €377 and departed from Dublin. The most popular routes on KAYAK are Dublin to Chicago which costs €813 on average, and Shannon to Chicago, which costs €987 on average.

What is the cheapest day to fly to Chicago?

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as €660. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are €779 on average.

What is the cheapest month to fly to Chicago?

The cheapest month for flights to Chicago is November, where tickets cost €413 on average for return flights. On the other hand, the most expensive months are July and August, where the average cost of tickets from Ireland is €720 and €712 respectively. For one-way flights, the best month to travel is February with an average price of €421.

What is the cheapest time of day to fly to Chicago?

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost €612 on average. The most expensive time of day to fly to Chicago is generally in the morning, which is peak travel time and where the average cost of a ticket is €710.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Dublin €619 return.

How far in advance should I book a flight to Chicago?

To get a below average price, you should book around 3 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Which is the cheapest airport to fly into in Chicago?

Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport (MDW), with an average flight price of €159.

Good to know – Book Cheap Chicago Plane Tickets

Low season

February

Cheapest flight

€304
Best time to beat the crowds (3% less expensive on average)
Most popular time to fly and prices are also 1% lower on average.
Flight from Shannon to Chicago O'Hare Airport

When to book flights to Chicago

Are your dates flexible? Find out the best times to travel to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated return price

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 5 days, the cheapest flight deal to Chicago was found on the route from Shannon, at €397 return. The most popular connection is from Dublin to Chicago, while KAYAK users have found return deals for as low as €397 in the last 5 days.

  • Which Chicago airport is closest to central Chicago?

    The distance between Chicago Midway Airport and the city centre of Chicago is 14 km, which makes it the closest of the 3 Chicago airports airports. Chicago O'Hare Airport is 26 km away from the centre and Chicago Greater Rockford is 126 km away.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs €903. The cheapest price found on KAYAK in the last 2 weeks cost €377 and departed from Dublin Airport.

  • How does KAYAK find such low prices on flights to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for €558 or less one-way and €735 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 5 airlines flying to Chicago

 
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.6
FinnairOverall score based on 1430 reviews
6.9Entertainment
7.7Boarding
7.4Comfort
8.2Crew
6.7Food
Airline reviews

Finnair was ok. But some things were pretty bad: 1. Crew was not friendly, especially a crew member named, Maria. She woke me up while I was deep asleep by force just to let me know that 2 people can’t be on the same seat (my toddler and me) for sleeping. 2. There was no vegetarian option in the menu so I had to eat bread for one meal 3. They didn’t have an option for child meal

2.0 MediocreDivya, Aug 2026
Read more Finnair reviews

Finnair was ok. But some things were pretty bad: 1. Crew was not friendly, especially a crew member named, Maria. She woke me up while I was deep asleep by force just to let me know that 2 people can’t be on the same seat (my toddler and me) for sleeping. 2. There was no vegetarian option in the menu so I had to eat bread for one meal 3. They didn’t have an option for child meal

The food was delicious. There has been a major improvement here in the last few years. Excellent, friendly service. An enjoyable experience.

Awful. Delayed for unknown reason. Boarded late, part of a Tight connection ands had to go through customs and immigration. And they lost my bags.

Late, dirty cabin, charging ports broken, uncomfortable, no tomato juice, barely edible food

Flight on time, landed well ahead of schedule. Attendants were excellent and responsive

The crew was friendly, and the flight landed on time

Rude Iberia security crew at the Madrid terminal. No Iberia officials to be found to redress complaints at the gate. No supervisors. Nothing for processing upgrades at the gate Iberia app did not work to let me upgrade my options to higher classes. No water was offered on a hot day in Madrid. Madrid airport air conditioning was so weak that people were sweating. Never book on any airlines that codeshare with Iberia.

Great if not for the boarding by bus at Heathrow terminal 3. Medieval disappointing time-consuming and very hard on handicapped flyers. It was awful

Do not use KAYAK or Finair for future travel. Unless you purchase the tickets directly from the airline, you were going to have a difficult time checking in. Kayak canceled my flights twice and ended up causing great difficulty in me getting back from Europe because they double sold my tickets between American Airlines and Finair. The event caused significant delays and led to me having to rebook my flights.

It was listed on my ticket as Finnair but there was no indication that the flight was Finnair. In fact the number was even different. There were no employees there until exactly 2 hours before so we had to wait in line at Iberia and hope

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Leaving at 7 when scheduled to leave at 4:20 - you tell me. Understood there was a ground stop. Then having to "reboot" the plane because of a lighting strike, also understood. But basically the flight was a "clusterf#$%".

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

ok, butt flght was delyed for 2,5h from Frankfurt, and next Flight to Columbuse same

Flight was great. Almost miss my connecting flight due to late departure from Haneda. Had to run all through airport in Chicago to make the flight. Experience was great for 1st time flyers using ANA Airlines.

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Seats are complete BS for 10 hrs. The guy at counter canceled our return flight from europe. Lufthansa on the way back made United look like a trailer park gathering. If given the opportunity, I will never fly united again. Lufthansa seats werent much better to be fair but the service was a 10 out of 10. Incant express how difficult umited made my trip.

It was a great experience to fly with ANA, the sit is very comfortable.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

The boarding time for this flight was ridiculous, longest in all my time flying. There was a problem with the original plane so it was switched at the last minute. Not a good substitution. We were delayed in departing. The bathrooms for economy were not adequate. The crew were pleasant but not present in the economy section, in an ~ 8hr flight only twice did they come through offering water, easy to get very dehydrated. I had to go and ask every hour for more water. The seats were cramped, and I have no idea what they did to the coffee but it was undrinkable. The food, was disgusting, utterly inedible, I am stunned by the lack of care and quality with the inflight service, very disappointing, I had expected better from Aer Lingus.

Very comfortable flight. Great service, food options, and entertainment options. With Wi-Fi!

Small plane. Tight seating . What can one say except that it was fast!

The flights are literally always delayed arriving, boarding and taking off so they are always late for the connection. I planned ahead so I was okay but many others aren't. The food was terrible. The staff was very pleasant. I appreciate boarding back to front.

All aspects were excellent - it helped that the flight was only 2/3 full and I had no one sitting in my row. The Pre-check (US Passport Control and Customs) in Dublin made everything so easy when we arrived in Chicago.

Very nice experience. Flight had good entertainment system and good food options. Customer service was very friendly and nice as well.

The same as I stated prior. We incurred extra costs that should be reimbursed, given we were not communicated with about schedule changes.

My flight from Dublin was delayed two hours which ment that I missed my connecting flight to Phoenix. American Airlines provided a hotel room and rebooked my flight for 7:30 AM the next day. I didn't get to the room until 11 pm and I had to be at the airport the next day by 5 AM. The airlines did their best but the schedule was challenging for an 81 year old.

I like Aer Lingus so that is why I’m writing this critique so they can become better. The boarding gate was too small to board properly. Our seats were toward the back of the plane knowing we would be boarding after business class, we moved to that area after business class boarded. An Aer Lingus employee told us we couldn’t stand there. We explained we were the next group to board and wouldn’t even be able to hear when our boarding was called. She didn’t care and was not very professional. The cabin was freezing. I wouldn’t feed my dog the food. We were over an hour late coming into chicago because of weather which can’t be avoided. I asked the crew if they could make an annoucement for before whose final destination is chicago to wait and allow the people with connecting to deplane first. He said there are a lot of people with connecting flights. He said, it doesn’t matter. Well, yes it does. He could have been more considerate of his passengers.

Very pleasant staff, there was some turbulence but the captain was very apologetic and gave notice where possible.

It was amazing. I sat in First Class as a Saga Premium member, and my service was top notch. It was wonderful. I only recently joined Saga Club since I do travel to Scandinavia often and enjoy flying through Reykjavik on Iceland Air versus other ways of travelling to Europe. This was my first trip sitting in first class, which I honestly wasn’t expecting!

There were no places to sit at the gate. Most people had to sit on the floor or stand waiting for the gate to open and board. We were told we needed passport and the person hardly looked at them. Maybe for 2 seconds. No announcement made asking to board by row or group. On a 5.5 hour flight the crew only came through the cabin 2 times offering water and buy everything else. For the price of the ticket at least offer free soda! The airliner was very comfortable

Crew was wonderful. I knew going in that the seats were not lie-flat in business class, but they reclined less than I expected. To save on waste, you have to ask for which pieces of the amenity kit you are interested in, which they will gladly give to you. Flight was fairly short, so no issues. I did have one piece of luggage not show up at terminal on landing. They were great about looking for it. Found it...it actually did make the flight and was listed as "not picked up" (?????--we stayed over an hour looking for it, including in the odd-sized baggage claim.) Since "not picked up" they will not ship to my house and I have to go back to airport, which is in another town. I probably could have pressed this issue, but headed back to airport for another flight anyway, so will pick up then.

It didn't happen. Icelandair cancelled the flight from Nuuk, Greenland to Reykjavik, Iceland so I couldn't fly to Portland. Additionally Icelandair rebooked me on a flight that got cancelled too.

How can the airline deploy the oldest 757-200 with a broken down entertainment system and no WiFi for a cross Atlantic 7:50 hr torture chamber experience?? My seat 3A couldn’t be reclined. The footrest was flimsy and useless. And there’s no leg support unlike their newer 737-Max which they lavish on intra-Europe routes. Shame!!

Only drinks included in economy class was water and coffee seat on the 737 were hard as rock. The landing and passport control in Iceland are the worst I have ever seen. 2 hours to clear customs ???? 3 attendants at pass port control out of more than a dozen closed. I” ll never fly to Iceland or transfer through this airport again.

At least one soda free, felt like I was nickeled to death.

Comfort of seats is not good. Like sitting on a rock for 6 hours. Also no in flight food and limited beverages unless you pay is not nice. Need flight to be dark during the “night” but attendants don’t ask for shades to be lowered..

Good. Lacking overhead bin space. No food offered but you can order online or in flight and pay for snacks.

We had to be bussed to the plane. And it was raining. Not a pleasant experience.

I want to highlight the crew members and their excellent work and professionalism. They work hard to make a long trip the most comfortable as possible, the food and drinks they offer are pretty good. And they are always asking if you need something else. I have had experiences with other airlines where you have to basically beg for a bottle of water. This is not the case. Highly recommended!!!

the blanket was great and pillow helped. really need a toothpick packed with meals

Very comfortable plane. The food was very good (for airplane food). The crew was great

The legroom was lacking and the entertainment system lacked adequate selection of older films. Modern films are generally not very good.

Perfect airline, super friendly, great service, tasty food. Would fly again.

Everything could have been better. What needed to be wrong with United went wrong

It was good. The seats in economy weren’t bad

Very good. Comfortable and I felt well taken care of from start to finish

We were in premium economy seats that appeared to be locked in plae, No reclining. My aching back.

I don’t understand how they charge as much as they do for such a poor experience

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Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago