$107 Find Cheap Flights from Connecticut to Illinois - Compare and Save

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Cheap Flights from Connecticut to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Chicago
2h 20mNonstop
from $235per person
Bloomington
5h 17m2 stops
from $339per person
Decatur
Decatur
6h 15m2 stops
from $376per person
Moline
4h 49m2 stops
from $377per person
Peoria
5h 01m2 stops
from $422per person
Champaign
Champaign
5h 53m2 stops
from $506per person
Useful Info

Good to know

Low season

January

Cheapest flight

$107
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from New Haven 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 airlines fly most frequently to Illinois?

    Connecticut and Illinois are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (33 flights per week), Southwest (29 flights per week), and Air New Zealand (28 flights per week).

  • How many airports are there in Illinois?

    There are 12 airports in Illinois. The busiest airport is Chicago O'Hare Airport (ORD), with 91% of all flights arriving there.

  • 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 $277.

  • 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 $468. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $593 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 afternoon, when round-trip flights cost $425 on average. Morning departures are around 12% 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 $506.

  • What is the cheapest flight to Illinois?

    The cheapest ticket to Illinois from Connecticut found in the last 5 days was to Chicago Midway Airport, at $130 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 5 days was $130.

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

    The cheapest month for flights from Connecticut to Illinois is May, when tickets cost $203 (return) on average. On the other hand, the most expensive months are February and January, when the average cost of round-trip tickets is $299 and $262 respectively.

  • How many cities have direct flights to Illinois?

    From Connecticut, there are direct flights to Illinois from 2 cities. The city with the most direct flights is Hartford, with 172 direct flights each week.

  • How many direct flights to Illinois are there each day?

    There are around 26 direct flights from within Connecticut to Illinois every day. Most flights (63%) depart in the morning.

  • How many direct flights to Illinois are there each week?

    Each week there are around 177 direct flights from within Connecticut to Illinois. The most common day for departures is Monday, with 16% of flights taking off on this day.

  • How long is the flight to Illinois?

    An average nonstop flight from Connecticut to Illinois takes 5h 27m, covering a distance of 823 miles. The shortest route is New York LaGuardia Airport (LGA) to Chicago Midway Airport (MDW) with an average flight time of 2h 20m.

  • How many long-haul flights are there to Illinois each week?

    There are not any long-haul (6-12 hour flight duration) or medium-haul (3-6 hour flight duration) flights to Illinois. Instead, there are 177 short-haul flights (up to 3 hour flight duration), with the most arriving from Hartford.

  • 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%) 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 4213 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

10.0 ExcellentLaura, Sep 2026
Read more Southwest reviews

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

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.

Packed old plane with uncomfortable seats. Great crew, especially Tara who was helpful to many. No water offered. Hard landing. Discount pricing is the benefit!

Flight was smooth. We boarded early and left Grand Rapids about a half hour ahead of schedule. We then arrived in Lakeland about 40 minutes early. Flights attendants (3) were welcoming and pleasant. Wish we would have at least been offered to buy a bottle of water. No beverage service at all.

I really liked the young man who checked me in and took my bags! He was so kind and was very helpful! I told my sister about the great service and him and she said that is why she flies Avelo Air.

The flight was delayed by a lot and the seats are pretty tight

Surprisingly was one of the better flights I’ve been on

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

Avelo provided exactly what I expected. They are a low-cost option with no frills but the experience was comfortable and the staff was great! I will be using them in the future for trips when cost is a priority for me.

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

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

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.

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline much.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

The price. Omg $1100. Was crazy and it was not clear on the website.

Excellent. I had a medical emergency on flight SNA-ORD and the attendants were very helpful.

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.

Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.

Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.

No WiFi, no power to charge phone, confusing boarding, delays

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

I volunteered to let them put my carry on suitcase in the baggage storage area. But when we landed I was told it was being unloaded IN A DIFFERENT TERMINAL! I had to walk (painful for me) a long way to retrieve my bag and my ride had to move from the waiting area they were in to a totally different one. Not happy.

Another American Airlines flight, another significant delay. At least this one wasn't canceled like many others have been. This time we sat on the runway at LaGuardia for 2.5 hours. By my count that is 7 American flights the last three months that have been delayed 2 hours or more or canceled entirely.

There was no clear update on the flight until last minute and made it an hour delay. No clear flight aircraft or incoming flight which we will be boarding. We would plan accordingly for our connecting flight. This is one one the worst service, I also had to buy an another ticket with different ai carrier. American airline was not letting me plan my trip, made us just waiting. Not a good service at all.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

My luggage was lost at some point during my layover between Chicago and LHR. I landed Tuesday morning, and did not get it until Thursday night. Ironically, the people at the ticket desk had added a “priority” sticker to my tracking tag.

My experience was fine, with one surprising exception. After leveling off at cruising altitude, the main cabin flight attendant made an announcement that he had a cold, so he would not be coming through the aisle to provide cabin service. He claimed this was in consideration of his health and safety and ours. However, if passengers wanted a beverage, he invited them to come to the back of he plane, where he would provide service. I understand that a flight attendant's primary responsibility is to ensure passenger safety, but a secondary role is to provide service. If this flight attendant was too sick to perform his duties - and if he truly cared about passenger health and safety , as he claimed - he should have stayed home and called in sick, rather than exposing the cabin to his germs.

The flight was delayed multiple times. Breakfast was not served and only an apology given and statement that we could find better pastries in Paris. Seats were extremely narrow and uncomfortable.

We waited over 30 minutes for a gate in Chicago and more than 15 minutes for the doors to open. Cookies were missing from the menu.

Flight was 2 hr late but at least I was upgraded to first class

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

We were stuck with no gate upon landing for 90 minutes. Unacceptable.

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