$40 Find Cheap Flights from Connecticut to Illinois

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Low seasonJanuary
High seasonJuly
Cheapest flight$40
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from New York John F Kennedy Airport to Chicago O'Hare Airport

FAQs for booking flights from Connecticut to Illinois

  • How does KAYAK find such low prices on flights from Connecticut to Illinois?

    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 from Connecticut to Illinois.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Illinois?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Connecticut to Illinois is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Connecticut to Illinois?

    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 from Connecticut to Illinois 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 from Connecticut to Illinois?

    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 from Connecticut to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which is the cheapest airport to fly into in Illinois?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Illinois is Chicago Midway Airport (MDW), with an average flight price of $246.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Wednesday where round-trip tickets can be as cheap as $442. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $530 on average.

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

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $436 on average. Morning departures are around 8% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $472.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Connecticut found in the last 72 hours was to Chicago Midway Airport, at $51 round-trip. The most popular route is Hartford (BDL) to Chicago Midway Airport (MDW) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $51.

  • What is the cheapest month to fly from Connecticut to Illinois?

    The cheapest month for flights from Connecticut to Illinois is October, when tickets cost $253 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $523 and $493 respectively.

  • How long is the flight to Illinois?

    An average nonstop flight from Connecticut to Illinois takes 5h 26m, covering a distance of 827 miles. The shortest route is New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW) with an average flight time of 2h 20m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (93% of total searches to Illinois). The next most popular destinations are St. Louis (6%) and Moline (0%). Searches for flights to Peoria (0%), to Evansville (0%) and to Springfield (0%) are also popular.

Reviews of the top 5 airlines serving from Connecticut to Illinois

 
Need help choosing which airline to fly with from Connecticut to Illinois? 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.
8.0
SouthwestOverall score based on 4252 reviews
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
7.6Entertainment
Airline reviews

It was one and half hour late... Not sure if any other experience matters.

4.0 OkaySudhir, Jul 2025LGA - MCI
Read more Southwest reviews

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Expect nothing and you will be fine. Seats are crammed.

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

You get what you pay for. The plane was dirty and the seats were awful.

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

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.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

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.

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.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

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.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Terrible communication with weather delay, lost baggage, near impossible to reach customer service

My tickets got canceled on me by your site and I didn't have a flight. Then you kept sending me emails on the status of q flight I didn't have tickets for.

The delay was ridiculous because nary a word escaped from the gate attendant regarding our flight status. It was a complete joke.

I missed a flight because of a delay. I had to buy a new ticket through Southwest.

The crew was mostly okay. The flight attendant who answered our questions was curt and unhelpful unfortunately. He seemed upset and I understand having off days.

Flight was delayed one hour. Notification to the crowd waiting near the gate was terrible…announcements were unclear and very hard to hear and therefore understand. Frontier does NOT send texts to notify, only email. The reader board over the gate itself was NEVER updated to indicate the gate had been changed. It’s like a bunch of children are running things.

I’m not gonna fly Frontier Airlines because booking is not an option. No water or food is for high price, not equipped for health emergency incompetent crew for emergency services. Cheap airline shows it is cheaper in all service categories. Boarding is the best of all airlines!

We’ve all seen the YouTube vids of out of control passengers. But this was an instance of a highly aggressive, bully flight attendant. Yelling in the face of a vet with PTSD who was texting their family. And no , we had not yet been instructed to put our phones in airplane mode. My suggestion is that you should pay whatever difference there is in order to avoid Frontier airlines. Additionally, after 3hrs trying to get customer service frontier offered a $25 voucher. I declined. This experience was so traumatic. To be verbally assaulted and abused by a flight attendant that has the power to say “boo” and I miss my flight ( which was to a family member’s funeral ). Frontier is unsafe and I cannot impress enough how much I discourage anyone ( esp those with any kind of disability like PTSD ) flying on Frontier.

My flight was delayed by two hours which made it so that I would miss my layover flight. I stood in line for customer service for over an hour and when I reached the agent she told me to scan a QR code and it'll give me options. I wasn't offered any help, guidance or compensation, only told that I have options but that I had to figure it all out myself. I was refunded part of the trip and had to buy an expensive same day ticket from another airline in order to get home. I will never fly Frontier again.

We were delayed three times ,and that destroyed my plans, and reservations

Book cheap flights from Connecticut to Illinois

Recent round-trip flight deals

8/19Tue
nonstopJetBlue
2h 58mJFK-ORD
8/25Mon
nonstopJetBlue
2h 12mORD-JFK
$70
8/12Tue
nonstopJetBlue
2h 48mJFK-ORD
12/16Tue
nonstopJetBlue
2h 13mORD-JFK
$77
8/5Tue
nonstopUnited Airlines
2h 39mLGA-ORD
8/9Sat
nonstopUnited Airlines
2h 22mORD-LGA
$91
9/4Thu
nonstopSouthwest
2h 20mLGA-MDW
9/8Mon
nonstopSouthwest
2h 10mMDW-LGA
$91
9/4Thu
nonstopAmerican Airlines
2h 41mLGA-ORD
9/8Mon
nonstopAmerican Airlines
2h 18mORD-LGA
$92
9/5Fri
nonstopUnited Airlines
2h 37mLGA-ORD
9/8Mon
nonstopUnited Airlines
2h 24mORD-LGA
$98
10/3Fri
nonstopSouthwest
2h 30mLGA-MDW
10/6Mon
nonstopSouthwest
2h 05mMDW-LGA
$98
9/16Tue
nonstopAmerican Airlines
2h 51mLGA-ORD
9/19Fri
nonstopAmerican Airlines
2h 00mORD-LGA
$100
10/2Thu
1 stopFrontier
12h 09mJFK-ORD
10/5Sun
1 stopFrontier
12h 09mORD-JFK
$159
7/24Thu
1 stopFrontier
8h 35mEWR-STL
7/26Sat
1 stopFrontier
8h 52mSTL-EWR
$160

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Recent one-way flight deals

11/12Wed
nonstopJetBlue
2h 48mJFK-ORD
$40
8/12Tue
nonstopJetBlue
2h 48mJFK-ORD
$44
8/13Wed
nonstopUnited Airlines
2h 37mLGA-ORD
$46
8/19Tue
nonstopSouthwest
2h 20mLGA-MDW
$46
9/11Thu
nonstopAmerican Airlines
2h 41mLGA-ORD
$47
9/12Fri
nonstopUnited Airlines
2h 37mLGA-ORD
$53
9/19Fri
nonstopSouthwest
2h 20mLGA-MDW
$53
10/4Sat
nonstopAmerican Airlines
2h 41mJFK-ORD
$67
8/19Tue
1 stopFrontier
7h 10mJFK-ORD
$77
8/19Tue
1 stopFrontier
7h 10mJFK-ORD
$78

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Last minute flights from Connecticut to Illinois

Last minute flight, train and bus deals

7/15Tue
multi-stopSpirit Airlines
14h 00mLGA-ORD
7/23Wed
nonstopSpirit Airlines
2h 09mORD-LGA
$183
7/15Tue
multi-stopFrontier
11h 18mJFK-ORD
7/15Tue
multi-stopFrontier
6h 04mORD-JFK
$185
7/15Tue
nonstopUnited Airlines
2h 38mLGA-ORD
8/12Tue
nonstopUnited Airlines
2h 20mORD-LGA
$187
7/15Tue
nonstopUnited Airlines
2h 42mEWR-ORD
8/12Tue
nonstopUnited Airlines
2h 34mORD-EWR
$210
7/15Tue
nonstopAmerican Airlines
2h 52mEWR-ORD
7/22Tue
nonstopAmerican Airlines
2h 30mORD-EWR
$225
7/15Tue
nonstopSouthwest
2h 20mLGA-MDW
7/22Tue
nonstopSouthwest
2h 10mMDW-LGA
$225
7/15Tue
nonstopDelta
2h 52mLGA-ORD
7/22Tue
nonstopDelta
2h 17mORD-LGA
$225
7/15Tue
multi-stopAmerican Airlines
7h 37mEWR-ORD
7/22Tue
nonstopAmerican Airlines
2h 30mORD-EWR
$235
7/15Tue
nonstopSouthwest
2h 20mLGA-MDW
7/22Tue
multi-stopSouthwest
7h 40mMDW-LGA
$245
7/15Tue
multi-stopDelta
3h 43mEWR-MDW
8/12Tue
multi-stopDelta
5h 10mMDW-EWR
$245

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Everything you need to know for your flight to Illinois

Cabin class types available on flights to Connecticut

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

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