$30 Find Cheap Flights from Illinois to Connecticut

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Low seasonFebruary
High seasonDecember
Cheapest flight$30
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 27% increase in price.
Flight from Chicago O'Hare Airport to New York LaGuardia Airport

FAQs for booking flights from Illinois to Connecticut

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

    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 Illinois to Connecticut.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Illinois to Connecticut 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 Illinois to Connecticut?

    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 Illinois to Connecticut 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 Illinois to Connecticut?

    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 Illinois to Connecticut 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 Connecticut?

    Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Connecticut is Tweed-New Haven Airport (HVN), with an average flight price of $159.

  • What is the cheapest flight to Connecticut?

    The cheapest ticket to Connecticut from Illinois found in the last 72 hours was to New Haven, at $82 round-trip. The most popular route is Chicago Midway Airport (MDW) to Hartford (BDL) and the cheapest round-trip airline ticket found on this route in the last 72 hours was $197.

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

    The cheapest month for flights from Illinois to Connecticut is September, when tickets cost $276 (return) on average. On the other hand, the most expensive months are May and December, when the average cost of round-trip tickets is $483 and $394 respectively.

  • How long is the flight to Connecticut?

    An average nonstop flight from Illinois to Connecticut takes 5h 44m, covering a distance of 834 miles. The shortest route is Chicago Midway Airport (MDW) to New York LaGuardia Airport (LGA) with an average flight time of 2h 00m.

  • What are the most popular destinations in Connecticut?

    Based on KAYAK flight searches, the most popular destination is New York (96% of total searches to Connecticut). The next most popular destinations are Providence (2%) and Hartford (2%). Searches for flights to New Haven (0%) are also popular.

Reviews of the top 5 airlines serving from Illinois to Connecticut

 
Need help choosing which airline to fly with from Illinois to Connecticut? 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 4244 reviews
7.6Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

4.0 OkayGreg, Jul 2025PDX - DEN
Read more Southwest reviews

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

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.

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.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

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 was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

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!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

My flight was scheduled for about 6:05 departure. There were 11 gate changes from 4-7pm and the flight was 3 hours delayed due to operational issues. The plane taxied around the airport for about half an hour before stopping to be de-iced. It would have been nice if we were alerted of the plan to de-ice prior to the 30 minute drive around the airport. The flight attendant was friendly, which was the only redeeming thing about this flight. As a former flight attendant for United, I was extremely disappointed.

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

They are still charging me after taking 466 and 833 for round trip from AR to to Bradley airport from 19 to 21. Then poor experience. Am hurt and I will say it on social media. Please stay away from this airline. I see in my bank account they are still taking 644. Am trying to stop it. I used to fly United airlines and I suggest that if you don't want extra charges and good service you go back there. American airlines delayed my flight again and I was late for my meeting, no recompensation but charging me over and over.

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

Good communication at the gate and very nice crew in the flight

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

First of all, we never got on the connecting flight to Denver. They delayed our flight for two hours. If we would have gotten on that flight, we would have been stuck in Denver for 13 hours. So we re- routed our flight for a straight through flight to Oklahoma two days later. THEN, they delayed that flight for two hours. After that we were able to finally get on our flight and come home. Frontier Airlines - one of the worst airlines I have ever been on.

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!

Book cheap flights from Illinois to Connecticut

Recent round-trip flight deals

8/6Wed
nonstopSpirit Airlines
2h 09mORD-LGA
8/11Mon
nonstopSpirit Airlines
2h 30mLGA-ORD
$81
9/4Thu
nonstopSpirit Airlines
2h 05mORD-LGA
9/13Sat
nonstopSpirit Airlines
2h 38mLGA-ORD
$88
9/13Sat
nonstopAmerican Airlines
2h 18mORD-EWR
9/16Tue
nonstopAmerican Airlines
2h 35mEWR-ORD
$147
9/9Tue
nonstopSouthwest
2h 10mMDW-LGA
9/23Tue
nonstopSouthwest
2h 25mLGA-MDW
$147
9/20Sat
nonstopAmerican Airlines
2h 18mORD-EWR
9/24Wed
nonstopAmerican Airlines
2h 37mEWR-ORD
$148
9/3Wed
nonstopSouthwest
2h 15mMDW-LGA
9/7Sun
nonstopSouthwest
2h 20mLGA-MDW
$152
8/13Wed
nonstopUnited Airlines
2h 13mORD-EWR
8/20Wed
nonstopUnited Airlines
2h 41mEWR-ORD
$159
9/12Fri
1 stopFrontier
5h 52mORD-JFK
9/14Sun
1 stopFrontier
12h 09mJFK-ORD
$159
8/12Tue
nonstopUnited Airlines
2h 18mORD-EWR
8/16Sat
nonstopUnited Airlines
2h 42mEWR-ORD
$163
8/20Wed
1 stopFrontier
15h 27mMDW-JFK
8/25Mon
1 stopFrontier
18h 27mJFK-MDW
$178

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Recent one-way flight deals

8/6Wed
nonstopSpirit Airlines
2h 09mORD-LGA
$30
7/29Tue
nonstopSpirit Airlines
2h 09mORD-LGA
$42
9/3Wed
nonstopSouthwest
2h 00mMDW-LGA
$69
9/9Tue
nonstopUnited Airlines
2h 17mORD-EWR
$74
11/12Wed
nonstopSouthwest
2h 00mMDW-LGA
$74
10/15Wed
nonstopAmerican Airlines
2h 22mORD-JFK
$75
10/18Sat
1 stopFrontier
5h 55mORD-JFK
$76
8/13Wed
1 stopFrontier
6h 08mORD-JFK
$83
8/5Tue
nonstopUnited Airlines
2h 21mORD-EWR
$84
8/6Wed
nonstopAmerican Airlines
2h 09mORD-LGA
$85

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Last minute flights from Illinois to Connecticut

Last minute flight, train and bus deals

7/19Sat
multi-stopFrontier
8h 50mSTL-JFK
7/26Sat
multi-stopFrontier
8h 39mJFK-STL
$210
7/19Sat
multi-stopFrontier
8h 52mSTL-EWR
7/24Thu
multi-stopFrontier
8h 35mEWR-STL
$218
7/19Sat
multi-stop
6h 37mORD-EWR
7/26Sat
multi-stop
7h 30mEWR-ORD
$220
7/19Sat
nonstop
2h 09mORD-LGA
7/23Wed
multi-stop
10h 34mLGA-ORD
$243
7/19Sat
nonstopSouthwest
2h 10mMDW-LGA
7/26Sat
nonstopSouthwest
2h 20mLGA-MDW
$264
7/19Sat
nonstopAmerican Airlines
2h 16mORD-EWR
7/26Sat
multi-stopAmerican Airlines
5h 35mEWR-ORD
$274
7/19Sat
multi-stopSouthwest
4h 20mMDW-LGA
7/26Sat
nonstopSouthwest
2h 20mLGA-MDW
$274
7/19Sat
nonstopAmerican Airlines
2h 16mORD-EWR
7/22Tue
nonstopAmerican Airlines
2h 44mEWR-ORD
$283
7/19Sat
nonstopUnited Airlines
2h 34mORD-EWR
7/20Sun
nonstopUnited Airlines
2h 38mEWR-ORD
$330
7/15Tue
multi-stopUnited Airlines
6h 11mSTL-EWR
7/19Sat
nonstopUnited Airlines
3h 05mEWR-STL
$375

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Everything you need to know for your flight to Connecticut

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