€261 Find Cheap Flights to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 28/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
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Cheap Flights to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for return flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent return flight deals to Chicago

Wed, 10 Sep - Wed, 1 Oct
Icelandair Logo
12:15 - 21:15DUB-ORD
15h 00m1 stop
Icelandair Logo
19:25 - 13:15ORD-DUB
11h 50m1 stop
€320Icelandair
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Wed, 10 Sep - Wed, 1 Oct
Icelandair Logo
12:15 - 18:15DUB-ORD
12h 00m1 stop
Icelandair Logo
19:25 - 13:15ORD-DUB
11h 50m1 stop
€321Icelandair
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Thu, 15 Jan - Thu, 22 Jan
Scandinavian Airlines Logo
12:30 - 16:45DUB-ORD
34h 15m1 stop
Scandinavian Airlines Logo
19:20 - 18:20ORD-DUB
17h 00m1 stop
€323Scandinavian Airlines
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Wed, 29 Oct - Tue, 4 Nov
British Airways Logo
10:20 - 19:45DUB-ORD
14h 25m1 stop
British Airways Logo
17:10 - 09:35ORD-DUB
10h 25m1 stop
€384British Airways
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Mon, 1 Sep - Tue, 9 Sep
British Airways Logo
15:20 - 11:55DUB-ORD
26h 35m1 stop
British Airways Logo
20:40 - 14:45ORD-DUB
12h 05m1 stop
€386British Airways
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Fri, 5 Sep - Mon, 15 Sep
American Airlines Logo
07:40 - 14:50SNN-ORD
13h 10m1 stop
American Airlines Logo
17:40 - 11:20ORD-SNN
11h 40m1 stop
€527American Airlines
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Tue, 16 Sep - Tue, 23 Sep
American Airlines Logo
21:15 - 14:50SNN-ORD
23h 35m1 stop
American Airlines Logo
20:40 - 20:35ORD-SNN
17h 55m1 stop
€528American Airlines
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Mon, 15 Sep - Mon, 22 Sep
United Airlines Logo
09:30 - 11:45SNN-ORD
8h 15mdirect
United Airlines Logo
18:02 - 10:15ORD-SNN
10h 13m1 stop
€609United Airlines
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Mon, 25 Aug - Sun, 31 Aug
United Airlines Logo
09:30 - 11:45SNN-ORD
8h 15mdirect
United Airlines Logo
15:00 - 10:15ORD-SNN
13h 15m2 stops
€611United Airlines
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Fri, 29 Aug - Sun, 31 Aug
Aer Lingus Logo
20:30 - 15:45ORK-ORD
25h 15m2 stops
Aer Lingus Logo
22:25 - 19:50ORD-ORK
15h 25m2 stops
€659Aer Lingus
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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?

These are the best round-trip prices found by users searching on KAYAK in the last 72 hours.

In the last 3 days, the cheapest flight deal to Chicago was found on the route from Dublin, at €276 return. The most popular connection is from Shannon to Chicago and KAYAK users have found return deals for as low as €477 in the last 3 days.

How much is a flight to Chicago?

The average and cheapest price for all round-trip flights to Chicago from each origin found by users searching on KAYAK in the last month.

A flight to Chicago costs €939 on average. The cheapest price found on KAYAK in the last 2 weeks cost €406 and departed from Shannon. The most popular routes on KAYAK are Shannon to Chicago which costs €784 on average, and Dublin to Chicago, which costs €828 on average.

See prices from:

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights to Chicago is November, where tickets cost €437 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 €647 and €580 respectively. For one-way flights, the best month to travel is November with an average price of €437.

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 €710 return.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 5 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 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 €146.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight€261
Best time to beat the crowds (13% less expensive on average)
Most popular time to fly (1% more expensive on average)
Flight from Dublin 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or returns with a duration up to 40 days. The information is for flights to Chicago based on your location. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs - booking Chicago flights

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Dublin, at €276 return. The most popular connection is from Shannon to Chicago and KAYAK users have found return deals for as low as €477 in the last 3 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 €939. The cheapest price found on KAYAK in the last 2 weeks cost €406 and departed from Shannon Airport.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where round-trip tickets can be as cheap as €617. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are €719 on average.

  • 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.

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

    The cheapest time of day to fly to Chicago is generally at night, when round-trip flights cost €606 on average. The most expensive time of day to fly to Chicago is generally in the afternoon, which is peak travel time and where the average cost of a ticket is €772.

  • How many direct flights to Chicago are there each week?

    Each week there are around 36 direct flights from within Ireland to Chicago. The most common day for departures is Wednesday, with 17% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for €870 or less one-way and €722 or less round-trip.
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Prefer to fly direct to Chicago?

 
Nonstop data is based off flight results for the next 60 days. Find direct flights from all airlines flying nonstop to Chicago.
Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Direct departures

Ireland to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Direct returns

Chicago to Ireland

Monday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Tuesday

ANA, Aer Lingus, Aeromexico, +74 more

ANA, Aer Lingus, +75 more

Wednesday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Thursday

ANA, Aer Lingus, Aeromexico, +75 more

ANA, Aer Lingus, +76 more

Friday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Saturday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

See more direct flights

Reviews of the top 5 airlines flying to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Ireland to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.4
United AirlinesOverall score based on 8909 reviews
7.7Boarding
7.0Entertainment
7.3Comfort
8.1Crew
6.6Food
Airline reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

4.0 OkayGary, Jul 2025PIA - ORD
Read more United Airlines reviews

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Everything went well. I made my connection which is always a concern.

Delightful flight, ahead of time with a super crew, thanks

I wish Aer Lingus offered free wifi and had power outlets at the seats. Overall, the flight was good. Seat back entertainment had some interesting options. Food and snack options were mediocre at best. I enjoyed the canned red wine.

This was the most expensive economy flight per minute of flight time ever. But the quality was lacking. Extremely Aer Lingus rude staff at LHR said that the flight from London to Dublin (Ireland) was “NOT international.” Horrified at the colonial and imperial perspective. Seats were dirty with trash in seat pockets. Airline doesn’t clean or care about hygiene and safety.

In business class overhead bins were minuscule. Had to use cabin staff to find a place for my carry-on bag. Boarding process was shambolic, as “passengers who needed assistance in boarding” absorbed an excessive amount of time and attention that Aer Lingus was apparently unprepared for.

Aer Lingus was fabulous.nhowever, Aiirfare Assist who Kayak routes me to to purchase tickets for m was awful. They messed up my reservation so bad that after about six hours on the phone with them over the week before departure, I had been choice but to show up at the airport. The Aer Lingus staff were amazing and got it sorted out but I would recommend not using Airfare Assist.

I had a great experience. I wasn’t sure what to expect but the crew helped me check my bags and made sure I got in the correct line to board. It was a bit of a walk to my gate so arrive early. I would recommend securing a flight that includes checking in your bag if you remotely think your baggage is over 10kg/22lbs. Be safe and upgrade unless you are carrying a backpack or weekend type baggage.

Dublin to Boston was decent. Food and entertainment was included and that was expected for the rate paid.

No entertained. food and beverages were not complimentary. they lost my checked luggage which made my 10 day vacation unpleasant.

Flight was on time. Boarding was quick and efficient. Seats were comfortable. Food was fine.

Boarded with no problems. Sat on the tarmac for an hour before taking off. We were the last ones on our connecting flight. Didn't think we were going to make it. Our flight to Iceland was similarly delayed. When we've flown other airlines, pilots have tried to make up time while in the air. This doesn't seem to be something that Icelandair does. We made all of our flights, but it was stressful and we didn't think it was going to happen based on the time we arrived.

The flight was delayed and as a consequence we missed our connecting flight. Were stuck for another 6h in Reykyavik. Appreciated that we got a generous food voucher at least. Would have liked to see more information upon arrival including a person waiting for connecting flight travellers and informing already that we will not catch the flight and directing us to the office dealing with the matter; unfortunately that didnt happen and we hence first needed to find out whether flight had indeed left already and then locate the adequate office to help us with booking us on the next connecting flight. Also my suitcase broke and it is not clear whether it is happened on the leg with Iceland Air from DC to Reykyavik or on the leg with Lufthansa from Reykyavik to Frankfurt. Finally, understood that it is a low cost company but at least provision of earplugs for free would have been nice, instead of making them buy.

Good service. No complementary food for international flight. WiFi kinda pricey. Got the job done for the right price.

Still one of my favorite airlines, but the entertainment options were a bit lacking. It didn't help that my screen didn't work on one of the legs of the trip.

The plane was very small and the aisle was so narrow that every time someone walked by they rubbed against me, so it was very uncomfortable.

Everything was good. Only issue comes from being vegan and flying. The food options are super limited.

Paid for a Premium seat...minimal recline, no footrest. Maybe slightly wider than a cheap economy seat. Zero chance of getting any rest on this plane

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..

Seats in premier saga class were narrow and hard. Very uncomfortable for a 5-hour flight.

Iceland airlines doesn't provide any meal on flight to and from New York, except water and soda. Airline over charge for checking in luggage. I'm really upset.

We were kicked off this flight by British Airways due to delays on our connecting flight also operated by British airways and were rebooked on a different carrier which delayed our arrival home by > 26 hours.

Everything about the flight check-in was smooth no line the plane is clean and bathroom

Excellent everywhere but Philly, the most rotten airport in the world.

Check in was not the greatest as had to talk to an agent to clarify things and then he transferred us to another agent who had difficulty processing my credit card as there was a system glitch and not a card error.

I was put into business class. Wow! My flight attendant was great! The food amazing’

The gate at London Gatwick had confusing signs for the different zones and the staff seemed harried because people didn't know when it was their turn to come to the desk. Plus, with there were too many carry-on bag travelers, myself included. The charge scheme for checking bags is frustrating. If you travel light, you want the freedom to leave as soon as you deplane. When you are forced to gate-check your bag simply because the flight is fully booked, you lose whatever time you'd hoped to save because you're still stuck waiting for your bag to come off the conveyor belt.

Safe arrival. Improvement on Time efficiency Effective Communication will be great.

Not so good with their baggage handling as they damaged one of my check in luggage

A good flight back to Tampa and thankfully although we had a 90 minute delay because of thunder storms from Charlotte to bottom iof Florida, it was a prudent to avoid these for a comfortable flight as opposed to being tossed around with turbulence.

All went well on the flight, not happy of course with having to pay for a seat and in hold luggage of £50

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Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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