€270 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 4/6. 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, 0 bags

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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest return fare
€495
Typical prices: €694-€518
JetBlue
Fri 8/5Sun 17/5
DUB - ORD • 1 stop
Cheapest direct flights
€501
Typical prices: €694-€518
Finnair
Fri 8/5Sun 17/5
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
Cheapest
Most popular
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travellers who book at least 3 weeks in advance save around 31% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 24% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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

Fri, 8 May - Sun, 17 May
JetBlue Logo
11:30 - 07:44
DUB
-
ORD
26h 14m
1 stop
JetBlue Logo
06:00 - 08:20
ORD
-
DUB
20h 20m
1 stop
€495JetBlue
Fri, 8 May - Sun, 17 May
JetBlue Logo
11:30 - 07:44
DUB
-
ORD
26h 14m
1 stop
JetBlue Logo
06:00 - 08:20
ORD
-
DUB
20h 20m
1 stop
€495JetBlue
Sun, 10 May - Wed, 13 May
JetBlue Logo
11:30 - 07:44
DUB
-
ORD
26h 14m
1 stop
JetBlue Logo
08:35 - 09:00
ORD
-
DUB
18h 25m
1 stop
€496JetBlue
Wed, 27 May - Wed, 3 Jun
Icelandair Logo
12:15 - 21:25
DUB
-
ORD
15h 10m
1 stop
Icelandair Logo
22:25 - 11:05
ORD
-
DUB
30h 40m
1 stop
€498Icelandair
Fri, 8 May - Sun, 17 May
Finnair Logo
09:30 - 11:30
DUB
-
ORD
8h 00mdirect
Finnair Logo
22:25 - 11:50
ORD
-
DUB
7h 25mdirect
€501Finnair
Wed, 27 May - Wed, 3 Jun
Icelandair Logo
12:15 - 21:25
DUB
-
ORD
15h 10m
1 stop
Icelandair Logo
22:25 - 11:05
ORD
-
DUB
30h 40m
1 stop
€507Icelandair
Sat, 2 May - Wed, 6 May
KLM Logo
06:15 - 14:15
ORK
-
ORD
14h 00m
1 stop
KLM Logo
17:10 - 14:40
ORD
-
ORK
15h 30m
1 stop
€563KLM
Thu, 28 May - Thu, 4 Jun
KLM Logo
13:05 - 21:36
SNN
-
ORD
14h 31m
1 stop
KLM Logo
06:07 - 11:10
ORD
-
SNN
23h 03m
1 stop
€568KLM
Sat, 2 May - Wed, 6 May
Delta Logo
06:15 - 14:15
ORK
-
ORD
14h 00m
1 stop
Delta Logo
13:36 - 10:20
ORD
-
ORK
14h 44m
2 stops
€568Delta
Sat, 2 May - Wed, 6 May
Delta Logo
06:15 - 14:15
ORK
-
ORD
14h 00m
1 stop
Delta Logo
11:08 - 10:20
ORD
-
ORK
17h 12m
2 stops
€568Delta
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 €495 return. The most popular connection is from Vienna to Chicago and KAYAK users have found return deals for as low as €627 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 €669 on average. The cheapest price found on KAYAK in the last 2 weeks cost €497 and departed from Dublin. The most popular routes on KAYAK are Dublin to Chicago which costs €634 on average, and Shannon to Chicago, which costs €792 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 €611. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are €758 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 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 September, where tickets cost €396 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 €659 and €638 respectively. For one-way flights, the best month to travel is September with an average price of €396.

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 €588 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 €720.

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 €534 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 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 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 €129.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight€270
Best time to beat the crowds but there is an average 2% increase in price.
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 €495 return. The most popular connection is from Vienna to Chicago and KAYAK users have found return deals for as low as €627 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 €669. The cheapest price found on KAYAK in the last 2 weeks cost €497 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 €537 or less one-way and €649 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 1386 reviews
8.2Crew
6.9Entertainment
7.5Comfort
7.7Boarding
6.7Food
Airline reviews

On a more than 8 hours flight was only one meal included, which I have never experienced before. Always two meals on the overseas flight. It was very weird.

4.0 OkayAnikó, Apr 2026
BUD - HEL
Read more Finnair reviews

On a more than 8 hours flight was only one meal included, which I have never experienced before. Always two meals on the overseas flight. It was very weird.

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

Positive: It was refreshingly easy and polite check-in and boarding staff. Flight was on time and Helsinki is a very well-signposted airport. Shopping was nice as well. Flight was not full and I had lots of space in economy. Flight was perfectly on time. Negative: Food and drink not very good, but that it is normal on any airline. Didn't expect anything else.

Business seating is soooo uncomfortable. You can sit straight up or lay down. You need pillows behind you because the back doesn’t lay down. Those are need to “prop” you up. The chair has no padding whatsoever. Food was gross. I’ve eaten on Finnair before and the food was exceptional. This time it gave 2 people in our party diarrhea. It was the chicken dish. I took 2 bites and didn’t eat anything more. The flight attendants were nice. You needed an additional lounge in Terminal D at DFW Airport. After waiting 40 minutes to enter, we finally gave up and went to a bar across from the club doors. I’m unsure if I’ll ever book a Finnair flight again.

It was a good flight, very comfortable seats for sleeping in business class. Probably the most comfortable business class seat I've ever had (20+ times in business class on various airlines). Service was good, but the only downside is my screen didn't work and it had to be reset multiple times to get it to shut off. I had to block my eyes because the screen was white almost the entire flight and I wore an eye mask when I slept. But when eating and reading in my seat, my eyes hurt because the only way to turn the screen off was reset it and the screen would only be off for a few minutes at a time.

Everything was wonderful! AirBus seats are more comfortable to sleep in as compared to the Boeing planes.

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.

It was okay. The airplane was a little smaller than a flight from Thailand to Helsinki.

Wish that everyone would board the back of the plane first. Also let kids on first. The gate wasn’t open at arrival and we waited 45 minutes to takeoff. They made up for time in the air.

This was an absolutely exceptional flight. The flight attendants were extremely attentive and very friendly. They seemed to go out of their way to make us comfortable and to make sure that we had everything we needed., We were in business and were very happy with the size and the details for our pods. We would definitely recommend Finnair and will definitely be flying with them again.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

Food and drink service was very low quality. The flight attendants in business class must have been short some staff. Service was sluggish and not much English was spoken

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

Just a bad day to fly. Flight was delayed from scheduled 6:50 pm departure to 8:50 pm. Combination of factors mostly related to weather at the destination airport (which is where the incoming flight originated) which delayed the inbound flight over an hour. Once on board, we taxied but had to hold again on the taxiway for 10 minutes or so. We did not get wheels up until after 9 pm. The flight was smooth but about 18 minutes from our destination, we had to hold for several minutes more due to weather at ORD. We finally landed at ORD about 11:08 pm (accounting for the time difference, that was about a 3 hour delay from our scheduled departure time). It felt like we were never going to get to our destination. But the flight crew and attendants were very good. The movie selection onboard was also very nice. Got to watch half of a movie just during our taxi from the gate at ATL due to the delay!

The crew was friendly. The plane was comfortable. In-flight wifi didn't work well at all. The ride was quite turbulent but understandable given the weather.

My issue is with the SkyWest terminal. The flight was not listed on the main airport flight screen list, and I had to do a Google search to locate the terminal and gate. We had to ask several airport employees where to locate the phantom gate. The airport did not provide adequate signage and was confusing. When we arrived, there was one vendor providing services that quickly closed, leaving zero options for food and drink while we waited hours for our delayed flight. The crew that assisted with check-in and boarding was VERY friendly.

Economy seats a bit small but other than that it was all good.

Checked in ok for 3 flights at the airport check-in desk, but apparently I was not checked in to my connecting flights even though I was assured that I was and had seats on all 3 flights. Aer Lingus departure was also delayed for 1.5 hours which gave no time to collect bags to go through customs.

No complimentary drinks or snacks offered on a 2 hour flight was disappointing but everything else went well

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.

I love the direct flights. It saves a lot of hassle and allows immigration and customs in Ireland, making arrival much easier.

Great. Has a problem with DOB. Fixed 4 us. Led to a 5 hour earlier flight to London!

One of the best flight experiences I've have had in along time. Would fly with them again.

So, the trip from Dublin to LA did not really happen because the flight took off before we could finish the transfer.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

The most uncomfortable seat i’ve ever had on a flight

Waiting area on top of stairs before Boarding the bus wasn’t great. Took a long time to load the bus to gate.

The real reason why the flying experience with Icelandair ---was mediocre was because of not being able to enter DC airspace yesterday evening. This obviously was out of your control and do realize this is a safety issue. I did notice---that everything was being done to get us to Washington Dulles and we did arrive at Dulles SAFELY with just a 4 hour delay. Thank you!

The staff was kind and helpful. There was no food, and you needed to bring your own earphones to use the entertainment, which I didn’t know.

They wouldn’t check in my luggage even though I had one checked bag prepaid. So I took my bag to the gate and tried to check it in there and two employees scolded me for bringing a large bag to the gate. I told them I was trying to check it in and that it was prepaid, and they said they couldn’t guarantee that it would arrive at my destination but they finally let me drop it off when boarding the plane and pick it up right after exiting the plane. There was no food, and there was no entertainment.

Overall satisfied and would fly with them again. They could improve the check-in efficiency at BOS, we got backed up because it seemed there were passengers requiring much more time for check in.

The customer service was unbeatable from the wheelchair assist team to the flight attendants. The pilot also did an excellent job managing the turbulence.

Delays at check-in, seemed like they were short ground staff at the time and some passengers needed extra processing.

Food - Non-Existent. You pay for everything. It is strictly Pay-to-Play!

Again, we paid $ 328.00 for specific seats are were assigned those seats.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Valparaiso
Benton Harbor
New Buffalo

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.