$42 Find Cheap Flights from Connecticut to Illinois

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

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

Save 20% or moreCompare multiple travel sites with one search.

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

Bundle and saveSave money when you bundle your flight + hotel.

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

Useful Info
Useful Info

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$42
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 16% lower on average.
Flight from Newark Liberty 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 $227.

  • What is the cheapest day to fly to Illinois?

    Based on KAYAK data, the cheapest day to fly to Illinois is Thursday where round-trip tickets can be as cheap as $441. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $534 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 $437 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 6h 20m, covering a distance of 821 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 (94% of total searches to Illinois). The next most popular destinations are St. Louis (6%) and Moline (0%). Searches for flights to Peoria (0%), to Springfield (0%) and to Evansville (0%) are also popular.

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 4285 reviews
8.0Comfort
8.6Crew
8.2Boarding
7.6Entertainment
7.1Food
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

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 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 crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

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

Everything was on time, we arrived early, everything worked well.

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Worst airline experience. They were rude and kept changing our seats and/or giving our seats away so our family didn’t get to sit with each other. Almost everyone we dealt with at both airports with this airline was rude. The app kept giving us wrong information making things take longer. Dealing with them before TSA can take close to an hour…longer than I’ve ever had to deal with before. Never using this airline again.

Book cheap flights from Connecticut to Illinois

Recent round-trip flight deals

7/4Fri
nonstopSpirit Airlines
2h 37mEWR-ORD
7/8Tue
nonstopSpirit Airlines
2h 18mORD-EWR
$85
7/8Tue
nonstopSpirit Airlines
2h 37mEWR-ORD
7/8Tue
nonstopSpirit Airlines
2h 18mORD-EWR
$87
7/15Tue
nonstopUnited Airlines
2h 40mLGA-ORD
8/13Wed
nonstopUnited Airlines
2h 18mORD-LGA
$97
8/13Wed
nonstopSouthwest
2h 20mLGA-MDW
9/3Wed
nonstopSouthwest
2h 00mMDW-LGA
$97
11/1Sat
nonstopAmerican Airlines
2h 58mJFK-ORD
11/5Wed
nonstopAmerican Airlines
2h 11mORD-JFK
$99
8/5Tue
nonstopSouthwest
2h 20mLGA-MDW
8/9Sat
nonstopSouthwest
2h 10mMDW-LGA
$117
8/5Tue
nonstopAmerican Airlines
2h 46mLGA-ORD
8/8Fri
nonstopAmerican Airlines
2h 04mORD-LGA
$120
8/12Tue
nonstopUnited Airlines
2h 42mEWR-ORD
8/15Fri
nonstopUnited Airlines
2h 13mORD-EWR
$143
6/25Wed
1 stopFrontier
5h 42mEWR-MDW
7/1Tue
1 stopFrontier
12h 05mMDW-EWR
$160
7/1Tue
1 stopFrontier
11h 35mEWR-ORD
7/9Wed
1 stopFrontier
6h 10mORD-EWR
$160

Search by stops

Search by airline

Search by price

Recent one-way flight deals

7/8Tue
nonstopSpirit Airlines
2h 37mEWR-ORD
$42
7/4Fri
nonstopSpirit Airlines
2h 35mLGA-ORD
$42
9/9Tue
nonstopAmerican Airlines
2h 41mJFK-ORD
$49
7/15Tue
nonstopUnited Airlines
2h 38mLGA-ORD
$49
7/22Tue
nonstopSouthwest
2h 20mLGA-MDW
$49
8/19Tue
nonstopAmerican Airlines
2h 40mBDL-ORD
$69
7/5Sat
nonstopUnited Airlines
2h 39mEWR-ORD
$69
9/3Wed
nonstopSouthwest
2h 25mLGA-MDW
$69
7/1Tue
1 stopFrontier
5h 42mEWR-MDW
$80
6/24Tue
1 stopFrontier
6h 30mEWR-ORD
$80

Search by stops

Search by airline

Search by price

Last minute flights from Connecticut to Illinois

Last minute flight, train and bus deals

6/18Wed
multi-stop
11h 04mLGA-ORD
7/9Wed
nonstop
2h 09mORD-LGA
$140
6/17Tue
multi-stopFrontier
6h 30mEWR-ORD
6/24Tue
multi-stopFrontier
6h 06mORD-EWR
$148
6/20Fri
multi-stopSpirit Airlines
9h 40mEWR-ORD
6/28Sat
nonstopSpirit Airlines
2h 18mORD-EWR
$172
6/20Fri
nonstopSpirit Airlines
2h 37mEWR-ORD
6/27Fri
nonstopSpirit Airlines
2h 18mORD-EWR
$224
6/20Fri
nonstopSouthwest
2h 25mLGA-MDW
6/27Fri
nonstopSouthwest
2h 10mMDW-LGA
$274
6/20Fri
multi-stopAmerican Airlines
6h 24mJFK-ORD
6/28Sat
multi-stopAmerican Airlines
4h 56mORD-JFK
$280
6/20Fri
nonstopUnited Airlines
2h 38mEWR-ORD
6/24Tue
nonstopUnited Airlines
2h 20mORD-EWR
$283
6/20Fri
multi-stopAmerican Airlines
5h 32mJFK-ORD
6/27Fri
multi-stopAmerican Airlines
4h 40mORD-JFK
$284
6/20Fri
nonstopSouthwest
2h 25mLGA-MDW
6/24Tue
nonstopSouthwest
2h 10mMDW-LGA
$293
6/20Fri
nonstopUnited Airlines
2h 38mEWR-ORD
6/28Sat
nonstopUnited Airlines
2h 21mORD-EWR
$300

Search by stops

Search by airline

Search by price

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.

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.