
Book Cheap Chicago to Connecticut Plane Tickets
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KAYAK's insights & trends for Chicago to Connecticut flights
Get data-powered insights and trends into flights from Chicago to Connecticut to help you find the cheapest flights, the best time to fly and much more.
How much is a round-trip flight from Chicago to Connecticut?
Flight prices are below average for this route right now.
Flights to Connecticut from Chicago usually cost between $297 and $479 in September.The lowest price found in the past 5 days was $277 on American Airlines (Sep 5-Sep 6).
What is the cheapest Chicago to Connecticut flight route?
The cheapest ticket to Connecticut from Chicago found in the last 5 days was to New Haven, at $117 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Hartford (BDL), and the cheapest round-trip airline ticket found on this route in the last 5 days was $277.
Can I save money by flying with a layover from Chicago to Connecticut?
No, with an average price for the route of $327, prices are generally cheapest when you fly direct.
Which airlines fly non-stop between Chicago and Connecticut?
There are 4 airlines that fly nonstop from Chicago to Connecticut. They are: American Airlines, Southwest, Avelo Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Avelo Airlines at $84 for a round-trip flight to New Haven (HVN). On average, Avelo Airlines offers the best prices for nonstop flights between Chicago and Connecticut.
Which airlines fly most frequently between Chicago and Connecticut?
Chicago and Connecticut are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (44 flights per week), Air New Zealand (37 flights per week), and American Airlines (29 flights per week).
How long does a flight from Chicago to Connecticut take?
The duration of a flight to Connecticut depends on your arrival airport. The shortest routes to Connecticut from Chicago are to Springfield, which takes 2h 01m, and New York, which takes 2h 22m.
Which cabin class options are there for flights between Chicago and Connecticut?
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.
Good to know
Low season | February |
|---|---|
High season | November |
Cheapest flight | $53 |
FAQs - booking Connecticut flights
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Reviews of the top 4 airlines serving from Chicago to Connecticut
Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.
Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.
Overall good, just screaming kids in the area the whole flight.
OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.
The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.
I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.
The staff was very friendly, professional, and courteous. The overall flight was a great experience.
Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.
All was good. I just had a hard time getting connected to the WiFi/internet during the flight
after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though
I'm not a fan of Southwest's model. I don't like the herding style of boarding.
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.
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.
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.
The stewards going to Tampa were amazing. A few of the ones coming back were cold and distant. The girl at the desk at boarding was actually rude.
Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.
It was a good experience, unfortunately my checked baggages were come late and not arrived on time.
Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.
It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.
The SFO lounge closes at 12 midnight. My flight took off at 2AM
It was extremely hot in the cabin the entire flight, vent air was worn
Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.
My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well
The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.
Late start, late arrival and very uncomfortable seats. No legroom, no elbow room because the person next to me was fat. I had to press myself toward the aisle or be rubbing arms with them. As a result, I was bumped every time someone passed in the aisle. But I couldn't get away from the hip encroachment. Who wants to rub hips with an oversized stranger for over 2 hours? I'm not fat, just tall and larger-than-average frame so I need to leg room but it would be nice if other peoples' body parts weren't squeezing under and over the arm of the seating. Why should it cost me so much for simple comfort so United can get a little more profit?
gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on
The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.
Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things
I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight
Long delays to board due to mechanical issues with plane.
Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak
The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN
I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.
The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.
Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times