$35 Find Cheap Flights from Connecticut to Illinois

1 adult

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 22% 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 seasonMay
Cheapest flight$35
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 10% 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 $221.

  • 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 $445. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $541 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 $440 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 $482.

  • 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 $136 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 $136.

  • 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 11m, 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 15m.

  • What are the most popular destinations in Illinois?

    Based on KAYAK flight searches, the most popular destination is Chicago (92% of total searches to Illinois). The next most popular destinations are St. Louis (7%) and Moline (0%). Searches for flights to Evansville (0%), to Peoria (0%) and to Bloomington (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 4294 reviews
7.6Entertainment
8.6Crew
8.2Boarding
7.1Food
8.0Comfort
Airline reviews

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

8.0 ExcellentJohn, Apr 2025PVD - FLL
Read more Southwest reviews

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.

Plz don't take away free bags and free seating

The seats were a bit cramped and worn, but otherwise okay.

I would have liked to arrive on time - not 5 hours late!

After a 3 hour layover in Denver my flight was delayed over 5 hours! No explanation; no assistance; no offer to provide compensation; no one at Southwest was willing to offer any assistance. 8 hours in the Denver airport - ridiculous!

It was a perfect flight in all aspects! Both legs!

Only one drink pass through the cabin for a 4 hour flight. Quite rough and bumpy landing.

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

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

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

The aircrew was solid, the flight was chill, I had no issues. The gate agent was not the best. I was trying to use a military bag upgrade to move my bag from under the seat to the overhead bins and he told me there’s no overhead bins on the plane, argued with me why booking put a military member in basic economy (I don’t really understand this) and made it an issue to even try to help me stating I’d have to call reservations to get a bag upgrade. When every other agent with United can add it at the gate, this man couldn’t be bothered.

They canceled our flight and left us stranded to figure it out

Everything was very good. Was able to change a make run flight leaving on direct earlier in the app -seamless!!! Well done

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.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

All was good expecting the seats need a bit of cushion. Besides that I can’t complain.

You get what you pay for, and the flights went smoothly. There’s no reclining chairs, no screens, And there isn’t always wifi, but the plane was clean and staff was friendly and the takeoff/landing were smooth.

The only positive is that the flight made it both ways. Getting charged for every little thing after the cost of the ticket itself is comical, considering how the plane and services are as bottom-tier as possible. The self check-in kiosks are useless. It’s nice to think that you can print your boarding pass, tag your checked bag, and then just drop it off. But no, they still make you go through the line once you finish- what’s the point of the self check-in then? Any questions for the staff seem like the biggest inconvenience and were met with condescending responses. This was my first and now last time ever flying with Spirit. After all the extra costs, subpar plane and staff, I see no value. I’d rather drive the 13 hours than give Spirit another dime.

The flight was fine however what started as a reasonable priced ticket could have become an overpriced ticket with additional charge for carry on as well as checked bag $79 per bag per person each way. Additional charge for choosing one’s seat, additional charge for beverage and snack, we were on what was described as a new plane yet there were no audio/visual on the jet. A bare bones service but not at a bare bones price. Will think twice before flying Spirit again. 😕

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

The reps working at the airport counter were dumber than a second coat of paint.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

Not very good. Paid in excess of $400 for assigned seating for my family and that was not provided. I want that money back.

The seats were hard molded plastic covered in plastic vinyl. And the scam to charge people extra to sit together. Don’t they know we can just ask someone to trade seats. And watching the staff separate young children from parents… super classy. We had to guilt them into offering up our seats. This companies policies suck. Don’t give them your money.

The seats were awful, hard plastic covered in sheet vinyl. The airline tries to scam you into paying extra to get seat together when the flight wasn’t full. They were going to separate a family with young children but my wife who had a row to herself gave up her seat so the young mom could be with her young boys. I’m never giving this airline my money again.

It was a short flight so no food or entertainment….

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

I’ve never traveled on Frontier before. If you want basic, no frills, friendly service at great prices then give them a fly!

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The worst flight of my life. Never will I fly frontier again

Book cheap flights from Connecticut to Illinois

Recent round-trip flight deals

5/28Wed
nonstopSpirit Airlines
2h 32mEWR-ORD
6/4Wed
nonstopSpirit Airlines
2h 21mORD-EWR
$72
5/28Wed
nonstopSpirit Airlines
2h 37mLGA-ORD
6/4Wed
nonstopSpirit Airlines
2h 09mORD-LGA
$74
5/13Tue
nonstopSouthwest
2h 20mLGA-MDW
5/14Wed
nonstopSouthwest
2h 05mMDW-LGA
$137
5/13Tue
nonstopAmerican Airlines
3h 09mJFK-ORD
5/14Wed
nonstopAmerican Airlines
2h 16mORD-JFK
$138
5/24Sat
nonstopUnited Airlines
2h 42mEWR-ORD
5/25Sun
nonstopUnited Airlines
2h 13mORD-EWR
$147
5/20Tue
nonstopAmerican Airlines
2h 39mJFK-ORD
5/22Thu
nonstopAmerican Airlines
2h 16mORD-JFK
$153
5/14Wed
nonstopUnited Airlines
2h 35mLGA-ORD
5/14Wed
1 stopUnited Airlines
6h 05mORD-LGA
$157
5/14Wed
nonstopSouthwest
2h 20mLGA-MDW
5/21Wed
nonstopSouthwest
2h 05mMDW-LGA
$157
5/15Thu
1 stopFrontier
18h 07mJFK-STL
5/20Tue
1 stopFrontier
15h 40mSTL-JFK
$181
5/14Wed
1 stopFrontier
18h 07mJFK-STL
5/20Tue
1 stopFrontier
15h 40mSTL-JFK
$188

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/20Tue
nonstopSpirit Airlines
2h 32mEWR-ORD
$35
5/28Wed
nonstopSpirit Airlines
2h 32mEWR-ORD
$37
5/29Thu
nonstopUnited Airlines
2h 38mLGA-ORD
$69
5/28Wed
nonstopSouthwest
2h 20mLGA-MDW
$69
6/17Tue
nonstopAmerican Airlines
2h 43mBDL-ORD
$79
7/9Wed
1 stopFrontier
8h 04mJFK-ORD
$88
6/3Tue
nonstopAmerican Airlines
2h 39mJFK-ORD
$89
6/25Wed
nonstopUnited Airlines
2h 37mLGA-ORD
$89
6/25Wed
nonstopSouthwest
2h 20mLGA-MDW
$89
8/16Sat
1 stopFrontier
18h 57mJFK-ORD
$92

Search by stops

Search by airline

Search by price

Last minute flights from Connecticut to Illinois

Last minute flight, train and bus deals

5/5Mon
multi-stop
6h 33mLGA-ORD
5/6Tue
nonstop
2h 05mORD-LGA
$163
5/2Fri
multi-stop
11h 59mEWR-ORD
5/7Wed
nonstop
2h 21mORD-EWR
$170
5/5Mon
nonstopUnited Airlines
2h 41mLGA-ORD
5/7Wed
nonstopUnited Airlines
2h 15mORD-LGA
$179
5/5Mon
multi-stopFrontier
18h 07mJFK-STL
5/11Sun
multi-stopFrontier
30h 35mSTL-JFK
$179
5/2Fri
multi-stopFrontier
11h 59mEWR-ORD
5/7Wed
multi-stopFrontier
8h 56mORD-EWR
$207
5/5Mon
nonstopUnited Airlines
2h 49mEWR-ORD
5/12Mon
nonstopUnited Airlines
2h 13mORD-EWR
$249
5/5Mon
nonstopAmerican Airlines
2h 46mLGA-ORD
5/8Thu
nonstopAmerican Airlines
2h 10mORD-LGA
$263
5/5Mon
nonstopSouthwest
2h 20mLGA-MDW
5/12Mon
nonstopSouthwest
2h 10mMDW-LGA
$264
5/5Mon
multi-stopSouthwest
6h 55mLGA-MDW
5/7Wed
multi-stopSouthwest
4h 30mMDW-LGA
$267
5/3Sat
multi-stopAmerican Airlines
5h 16mLGA-STL
5/10Sat
nonstopAmerican Airlines
2h 28mSTL-LGA
$285

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.