€320 Find Cheap Flights to Chicago – Compare and Save

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 5/10. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest return fare
€469
Multiple Airlines
Thu 24/12Sat 2/1
SNN - ORD • 1 stop
Cheapest direct flights
€531
Typical prices: €405-€568
Aer Lingus
Tue 22/9Tue 24/11
DUB - ORD • Direct
Top airlines
Most flights • 14 per week
Best reviews • 7.7 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 33% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
Most popular
Good to know
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+1
+1
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Flight Deals
Booking Insights
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, 24 Dec - Sat, 2 Jan
Multiple Airlines Logo
07:50 - 13:45SNN  Shannon-ORD Chicago O'Hare Intl
11h 55m1 stop London Heathrow
Multiple Airlines Logo
17:10 - 11:30ORD  Chicago O'Hare Intl-SNN Shannon
12h 20m1 stop London Heathrow
€469Multiple Airlines
Thu, 5 Nov - Fri, 13 Nov
Multiple Airlines Logo
07:50 - 13:45SNN  Shannon-ORD Chicago O'Hare Intl
11h 55m1 stop London Heathrow
Multiple Airlines Logo
17:10 - 15:45ORD  Chicago O'Hare Intl-SNN Shannon
16h 35m1 stop London Heathrow
€469Multiple Airlines
Thu, 10 Sep - Mon, 14 Sep
Aer Lingus Logo
11:35 - 14:00DUB  Dublin-ORD Chicago O'Hare Intl
8h 25mdirect
Aer Lingus Logo
21:15 - 14:50ORD  Chicago O'Hare Intl-DUB Dublin
11h 35m1 stop London Heathrow
€530Aer Lingus
Tue, 22 Sep - Tue, 24 Nov
Aer Lingus Logo
11:35 - 14:00DUB  Dublin-ORD Chicago O'Hare Intl
8h 25mdirect
Aer Lingus Logo
15:55 - 05:15ORD  Chicago O'Hare Intl-DUB Dublin
7h 20mdirect
€531Aer Lingus
Sat, 29 Aug - Sat, 5 Sep
Finnair Logo
09:30 - 11:30DUB  Dublin-ORD Chicago O'Hare Intl
8h 00mdirect
Finnair Logo
22:20 - 11:50ORD  Chicago O'Hare Intl-DUB Dublin
7h 30mdirect
€534Finnair
Thu, 27 Aug - Sat, 5 Sep
Finnair Logo
09:30 - 11:30DUB  Dublin-ORD Chicago O'Hare Intl
8h 00mdirect
Finnair Logo
22:20 - 11:50ORD  Chicago O'Hare Intl-DUB Dublin
7h 30mdirect
€534Finnair
Sat, 19 Sep - Sat, 3 Oct
American Airlines Logo
11:45 - 19:38DUB  Dublin-ORD Chicago O'Hare Intl
13h 53m1 stop Charlotte Douglas
American Airlines Logo
16:45 - 09:35ORD  Chicago O'Hare Intl-DUB Dublin
10h 50m1 stop Charlotte Douglas
€557American Airlines
Sat, 19 Sep - Fri, 2 Oct
American Airlines Logo
11:45 - 19:38DUB  Dublin-ORD Chicago O'Hare Intl
13h 53m1 stop Charlotte Douglas
American Airlines Logo
21:01 - 09:35ORD  Chicago O'Hare Intl-DUB Dublin
30h 34m1 stop Charlotte Douglas
€557American Airlines
Wed, 2 Dec - Sun, 6 Dec
United Airlines Logo
10:40 - 13:20DUB  Dublin-ORD Chicago O'Hare Intl
8h 40mdirect
United Airlines Logo
18:30 - 08:10ORD  Chicago O'Hare Intl-DUB Dublin
7h 40mdirect
€631United Airlines
Wed, 2 Dec - Sun, 6 Dec
United Airlines Logo
10:40 - 13:20DUB  Dublin-ORD Chicago O'Hare Intl
8h 40mdirect
United Airlines Logo
18:30 - 08:10ORD  Chicago O'Hare Intl-DUB Dublin
7h 40mdirect
€633United 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?

These are the best return prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Shannon, at €469 return. The most popular connection is from Dublin to Chicago, while KAYAK users have found return deals for as low as €529 in the last 5 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 €903 on average. The cheapest price found on KAYAK in the last 2 weeks cost €486 and departed from Dublin. The most popular routes on KAYAK are Dublin to Chicago which costs €825 on average, and Shannon to Chicago, which costs €1,056 on average.

See prices from:

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where round-trip tickets can be as cheap as €658. On the other hand, the most expensive day to fly is Monday, where round-trip prices are €811 on average.

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 round-trip 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 €412 on average for return flights. On the other hand, the most expensive months are August and July, where the average cost of tickets from Ireland is €736 and €718 respectively. For one-way flights, the best month to travel is February with an average price of €424.

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

The average price for all round-trip flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago is generally in the evening, when round-trip flights cost €606 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 €706.

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 €692 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 33% 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 €126.

Good to know – Book Cheap Chicago Plane Tickets

Low season

January

Cheapest flight

€320
Best time to beat the crowds (8% 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
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 5 days, the cheapest flight deal to Chicago was found on the route from Shannon, at €469 return. The most popular connection is from Dublin to Chicago, while KAYAK users have found return deals for as low as €529 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 €486 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 €579 or less one-way and €782 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

 
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.
7.7
FinnairOverall score based on 1427 reviews
7.4Comfort
6.7Food
6.9Entertainment
8.2Crew
7.7Boarding
Airline reviews

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

10.0 ExcellentMatti, Jul 2026
Read more Finnair reviews

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

All reviews good because...flight from BWI to London ,economy seats was miserable. I usually book 1,step up from economy but this would have added 1500 bucks 1 way. Bit the bullet and upgraded for retun flight, otherwise all ratings would have been rock bottom.

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

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.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

Gluten free snack options and meals that offer both gluten free and dairy free.

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

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

On time departure and arrival at LAX - good inflight entertainment - all basic seats on every airline right now begin to feel small after 10 hours!!

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.

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.

The ticket was reserved in my name but not paid for by underpricer. Alaska airlines was unable to issue my ticket (could not connect the ticket with the PNR) due to an error with underpricer and I spent the better part of 2 hours at the ticket counter trying to rectify.

Terrible way of boarding in Reykjavik. Seats comfortable. Meal was good.

Unlike my prior three connections on this latest journey, this flight was fairly good. Only issue was boarding as it was once again one of those Icelandic issues of bunch up, walk in the rain to a bus that then has you run up three flights of stairs to board the plain. I was in Saga class but the bus scramble eliminates any chance you get on first and have to then find a place to squeeze your carry on into an overhead that the people in economy populate so they can grab it on their way out up front. But unlike other Icelandic flights this journey I did find more the of the business class like accommodations then the other air segments. This one found a pillow and blanket waiting for me and I actually received a small cup of sparkling wine and had a bottle of water in place. Service was attentive and the flight departed and arrived on time. Received a menu and had choices of a hot or cold meal. I choose the hot which was cod and it was good. Decent size portion, salad and a choice of dinner rolls. Beverage menu was a selection of wines, beer and soft drinks. Desert was a small Tiramisu. Overall the six hour flight was a good experience for the price point.

We paid for saga class, which is the business class for international. My seat was broken and did not recline and my monitor for in-flight entertainment was broken.

The flight itself was fine, even with a one-hour delay leaving on the Reykjavik tarmac (the lost time was made up during flight). Our experience at the Reykjavik airport on arrival was terrible due mostly to the one hour it took for passport control. Only two stations were open for our category, and the room was full with a huge crowd.

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.

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

I wish the plane had pod seating for business class. I had a window seat (8K) and I had to climb over the person sitting on the aisle when I needed to get up. Also there is no partition between the seats for privacy when sleeping. The Asian airlines have much nicer business class seating. Their seats are wider for better comfort when sleeping.

The seat space seemed small especially when the person ahead reclined but other than that, very good.

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Everything you need to know for your flight to Chicago

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.