€255 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 19/5. 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
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Everything you should know

Cheapest return fare
€470
Typical prices: €666-€511
JetBlue
Fri 8/5Sun 17/5
DUB - ORD • 1 stop
Cheapest direct flights
€511
Typical prices: €706-€519
Finnair
Fri 8/5Thu 14/5
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 30% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 23% 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
10:40 - 20:53
DUB
-
ORD
16h 13m
1 stop
JetBlue Logo
06:00 - 08:20
ORD
-
DUB
20h 20m
1 stop
€470JetBlue
Fri, 8 May - Sat, 16 May
JetBlue Logo
10:40 - 20:53
DUB
-
ORD
16h 13m
1 stop
JetBlue Logo
07:20 - 08:20
ORD
-
DUB
19h 00m
1 stop
€473JetBlue
Fri, 8 May - Sun, 17 May
JetBlue Logo
10:40 - 20:53
DUB
-
ORD
16h 13m
1 stop
JetBlue Logo
06:00 - 08:20
ORD
-
DUB
20h 20m
1 stop
€476JetBlue
Thu, 16 Apr - Mon, 20 Apr
Icelandair Logo
14:15 - 18:15
DUB
-
ORD
10h 00m
1 stop
Icelandair Logo
19:25 - 13:15
ORD
-
DUB
11h 50m
1 stop
€483Icelandair
Fri, 17 Apr - Fri, 24 Apr
Icelandair Logo
12:15 - 21:25
DUB
-
ORD
15h 10m
1 stop
Icelandair Logo
22:25 - 11:05
ORD
-
DUB
30h 40m
1 stop
€484Icelandair
Mon, 27 Apr - Fri, 8 May
American Airlines Logo
11:45 - 17:58
DUB
-
ORD
12h 13m
1 stop
American Airlines Logo
16:17 - 09:35
ORD
-
DUB
11h 18m
1 stop
€487American Airlines
Tue, 28 Apr - Tue, 5 May
Delta Logo
06:15 - 14:15
ORK
-
ORD
14h 00m
1 stop
Delta Logo
13:36 - 14:40
ORD
-
ORK
19h 04m
2 stops
€563Delta
Tue, 28 Apr - Tue, 5 May
KLM Logo
06:15 - 14:15
ORK
-
ORD
14h 00m
1 stop
KLM Logo
16:20 - 16:40
ORD
-
ORK
18h 20m
1 stop
€567KLM
Tue, 28 Apr - Tue, 5 May
Delta Logo
06:15 - 18:13
ORK
-
ORD
17h 58m
2 stops
Delta Logo
17:04 - 14:40
ORD
-
ORK
15h 36m
2 stops
€568Delta
Sat, 11 Apr - Tue, 21 Apr
KLM Logo
10:00 - 18:40
DUB
-
MDW
14h 40m
1 stop
KLM Logo
12:52 - 08:45
MDW
-
DUB
13h 53m
1 stop
€570KLM
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 €470 return. The most popular connection is from Vienna to Chicago and KAYAK users have found return deals for as low as €604 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 €691 on average. The cheapest price found on KAYAK in the last 2 weeks cost €467 and departed from Dublin. The most popular routes on KAYAK are Dublin to Chicago which costs €642 on average, and Shannon to Chicago, which costs €783 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 €625. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are €748 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 €406 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 €636 and €628 respectively. For one-way flights, the best month to travel is September with an average price of €405.

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 €600 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 €717.

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 €548 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 30% 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 €131.

Good to know – Book Cheap Chicago Plane Tickets

Low seasonJanuary
Cheapest flight€255
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly (2% 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 €470 return. The most popular connection is from Vienna to Chicago and KAYAK users have found return deals for as low as €604 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 €691. The cheapest price found on KAYAK in the last 2 weeks cost €467 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 €546 or less one-way and €632 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 1376 reviews
7.7Boarding
7.5Comfort
8.2Crew
6.9Entertainment
6.7Food
Airline reviews

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

10.0 ExcellentFrancesca, Mar 2026
LHR - BOS
Read more Finnair reviews

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.

We had an excellent trip with Finnair. This was our first time and we’re very pleased. The only issue was with the boarding - it was a little bit confusing and needs a little bit of streamlining.

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!

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

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.

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

Like - the crew were nice Dislike - sitting on the tarmac for long periods after boarding and landing.

I was not admitted to the flight!!! i need a refund for this.

It’s my new favourite airline! Everything was smooth and relaxed!

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.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

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!

Nice, quick flight. There were lots of empty seats so they told me I could sit next to the emergency exit where I would have more legroom.

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!

Travelling to a place near Chicago?

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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.