€319 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 9/9. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
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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Flight Deals

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

Thu, 30 Oct - Tue, 4 Nov
 Logo
17:15 - 15:20DUB-ORD
27h 05m1 stop
 Logo
17:20 - 15:45ORD-DUB
16h 25m1 stop
€394
Find Deal
Fri, 17 Oct - Mon, 20 Oct
Scandinavian Airlines Logo
12:20 - 16:10DUB-ORD
33h 50m2 stops
Scandinavian Airlines Logo
19:15 - 10:55ORD-DUB
33h 40m2 stops
€395Scandinavian Airlines
Find Deal
Sat, 27 Dec - Tue, 30 Dec
American Airlines Logo
10:55 - 18:45DUB-ORD
13h 50m1 stop
American Airlines Logo
18:45 - 12:10ORD-DUB
11h 25m1 stop
€398American Airlines
Find Deal
Fri, 26 Dec - Mon, 5 Jan
British Airways Logo
08:50 - 18:45DUB-ORD
15h 55m1 stop
British Airways Logo
20:45 - 15:20ORD-DUB
12h 35m1 stop
€400British Airways
Find Deal
Thu, 23 Oct - Wed, 5 Nov
British Airways Logo
10:40 - 18:15DUB-ORD
13h 35m1 stop
British Airways Logo
21:45 - 17:00ORD-DUB
13h 15m1 stop
€402British Airways
Find Deal
Sat, 13 Sep - Mon, 29 Sep
United Airlines Logo
09:20 - 20:11DUB-ORD
16h 51m1 stop
United Airlines Logo
20:20 - 09:45ORD-DUB
7h 25mdirect
€407United Airlines
Find Deal
Thu, 4 Sep - Wed, 10 Sep
United Airlines Logo
09:20 - 14:55DUB-ORD
11h 35m1 stop
United Airlines Logo
20:20 - 09:45ORD-DUB
7h 25mdirect
€409United Airlines
Find Deal
Thu, 23 Oct - Wed, 29 Oct
Aer Lingus Logo
16:40 - 19:00DUB-ORD
8h 20mdirect
Aer Lingus Logo
18:45 - 07:05ORD-DUB
7h 20mdirect
€426Aer Lingus
Find Deal
Thu, 4 Sep - Wed, 10 Sep
Aer Lingus Logo
16:40 - 19:00DUB-ORD
8h 20mdirect
Aer Lingus Logo
15:45 - 05:10ORD-DUB
7h 25mdirect
€434Aer Lingus
Find Deal
Tue, 23 Dec - Tue, 20 Jan
American Airlines Logo
07:50 - 18:45SNN-ORD
16h 55m1 stop
American Airlines Logo
18:45 - 16:45ORD-SNN
16h 00m1 stop
€533American Airlines
Find Deal
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 Shannon, at €393 return. The most popular connection is from Dublin to Chicago and KAYAK users have found return deals for as low as €394 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 €798 on average. The cheapest price found on KAYAK in the last 2 weeks cost €246 and departed from Dublin. The most popular routes on KAYAK are Dublin to Chicago which costs €682 on average, and Shannon to Chicago, which costs €862 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 January, where tickets cost €426 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 €608 and €587 respectively. For one-way flights, the best month to travel is January with an average price of €426.

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 €468 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 3 weeks before departure, which saves you about 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 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 seasonJanuary
Cheapest flight€319
Best time to beat the crowds (15% less expensive on average)
Most popular time to fly (2% more expensive 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
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 Shannon, at €393 return. The most popular connection is from Dublin to Chicago and KAYAK users have found return deals for as low as €394 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 €798. The cheapest price found on KAYAK in the last 2 weeks cost €246 and departed from Dublin 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 €623. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are €715 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 €793.

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

    Each week there are around 35 direct flights from within Ireland to Chicago. The most common day for departures is Friday, with 14% 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 €710 or less one-way and €589 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, +72 more

ANA, Aer Lingus, +73 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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, +72 more

ANA, Aer Lingus, +73 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +73 more

ANA, Aer Lingus, +74 more

Friday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 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 8943 reviews
7.7Boarding
7.1Entertainment
7.3Comfort
8.1Crew
6.6Food
Airline reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

8.0 ExcellentAnonymous, Aug 2025YOW - ORD
Read more United Airlines reviews

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

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.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

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.

A little late, but an overall pleasant flight. Staff pleasent hand helpful, a great start to our holiday.

Not JetBlue's fault but Aer Lingus never explained how to transfer to JetBlue.

We had a long delay leaving IOM. No food or drunk service as it is a short flight. Shuttled by bus from terminal to plane with packed in conditions on bus.

Overall it was good experience and it was my first trip with Aer Lingus. One thing I was embarrassed was that someone occupied my seat so I was asked to use another seat. Due to this unhappy happening I almost missed the connecting flight because the random seat was far from the flight door. Food was fine, I liked the macaroni and cheese with fresh bread.

The space between seats was reduced even further. Could not even open the tray table fully and got compressed the moment the front guy reclined. For a long haul flight it was extremely uncomfortable.

Not satisfying due to loss Luguage for 4days. Damage Luguage that had no way to fill up a report for and me as a client to spend more money and time to replace it. Thank you for soliciting my opinion, but it was unfortunately a very disappointing experience. Stephanie Zvi

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.

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.

Best smelling onboard bathrooms ever. Even after use the whole flight. Biggest overhead bins. Most legroom in economy class. Great Icelandiic music. Really nice staff. Icelandair is awesome! (Don’t fly Air Canada! During the strike they lied about no flights available (I booked this flight myself) and hid the process to get money back on their website by obscuring menu titles, then made it difficult and time consuming to fill out. I’m Canadian. Don’t trust Air Canada!

It was good. The air plane is clean and staff were friendly.

Worst airline I’ve ever flown. Delayed 5.5 hrs, missed connecting flight, and missed an entire day of vacation. Zero customer service

Everything sucked. No food, one small glass of water, a tiny coffee, 5.5 hour delay with no customer service. Would never recommend flying them.

The crew was wonderful at check in, the gate and on board. Felt the luggage had more room than the passengers. The seats were smaller than most domestic U.S. airlines. I'm only 5'2" and I had little legroom. There were only 2 bathrooms in coach. Needed more. The flight was very smooth but not the most comfortable.

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.

We missed the connection because we had to wait for a shuttle from the plane to the Terminal. Also, we needed assistance and none was available.

When we arrived at the airport - 1st step - printing out your boarding pass - no issue. Not long lines as these machines. 2nd step - processing your bag drop off. There was only one associate there to help 10 kiosks. We had a family in front of us for 20 minutes trying to work on the machine and figure out every step for 4 pieces of luggage. My husband alerted the associate who was able to assist the family. Highly suggest that there are more associates to assist in this process. Besides this issue, security check went very quickly. Our flight was direct to Philadelphia. We had to carry our bags down two flights of steps, then out to the tarmac to a bus, then carry our bags up two flights of stairs to the plane. No one on the flight was expecting that long trek. I could see some people were struggling a bit. All in all - great flight crew, plane was clean and food was great!

There were no gluten-free vegan options available, so food was very limited on this flight, and some of the crew weren’t especially helpful about it. To make matters worse, a passenger was sick on board, and although the area was cleaned, the smell lingered for the rest of the journey. On top of that, we ended up circling for an extra hour, which only made the unpleasant situation drag on even longer.

Checking in prior on line and wait time at Gatwick was terrible. I would rate a big fat ZERO.

There was a slight delay. Otherwise, everything else was satisfactory.

The company that I bought my tickets through, Cheapflightsfares, failed to provide my confirmation information in a timely manner, so I was unable to check on at the country and therefore unable to make my flight. As a matter of fact, I STILL have not received the confirmation. After having read more and more reviews about the company, Cheapflightsfares appears to have scammed hundreds of hopeful travelers out of thousands of dollars. Please look into this company and, for the sake of anyone planning their next trip, stop allowing them to do business through you.

I checked in to bags, one arrived one was delayed. I did not receive the bag for 4 days - arrived on Tuesday, received bag on Saturday!

It was ok. Our flight was delayed 2 hours, and then again on arrival. The explanation given felt feeble.

The plane was known to be late in advance of takeoff. My guess is that it was known to be late at 11am or 5 hours before scheduled takeoff time. We were late to leave and with a wheelchair and the a cart, we only made it to gate. We raced! Inside plane, all was great

The booking agent, cheapflightsfares, messed up, and the information for the seats we paid extra for was not sent to American Airlines. We were separated on the return flight and sent to the lowest economy section. The flight attendant helped arrange seating at the back of the plane to allow my wife and me to sit together.

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