$72 Find Cheap Flights from Chicago to Connecticut - Compare and Save

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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 typical for this route right now.

Flights to Connecticut from Chicago usually cost between $277 and $378 in September.
The lowest price found in the past 5 days was $279 on Multiple Airlines (Sep 22-Sep 26).

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 $58 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 $283.

Can I save money by flying with a layover from Chicago to Connecticut?

No, with an average price for the route of $295, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago to Connecticut?

The cheapest month for flights from Chicago to Connecticut is October, when tickets cost $306 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $503 and $464 respectively.

Good to know

Low season

February

Cheapest flight

$72
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago to New Haven

FAQs - booking Connecticut flights

  • Where are the most common layovers between Chicago and Connecticut?

    If your flight has one or more stops, you might need to endure layovers at Philadelphia International Airport (PHL), Dulles International Airport (IAD) or Ronald Reagan Washington National Airport (DCA).

  • Which airlines are the best choices for those with kids?

    Many airlines, like American Airlines, will allow parents with young children to board early so they're able to enjoy successful flights. Some, like Delta, will also provide kids with activity kits to help keep them busy on flights.

  • Will I be able to take a pet with me on a flight from Chicago to Connecticut?

    Yes, you will be able to fly with a pet as your carry-on when you're flying to Connecticut through most airlines, but you will need to meet certain requirements. If you're flying with Delta, for instance, your pet will need to be at least 8 weeks old and in good health. It will need to be vaccinated for rabies and fit into a kennel that is no larger than 18 x 11 x 11 inches.

  • What steps can I take to make a flight from Chicago to Connecticut sustainable?

    If you're worried about the sustainability of a flight from Chicago to Connecticut, fly with an airline like American Airlines. They've updated their fleet with fuel-friendly flights and invested in electric equipment to reduce their carbon emissions, with a goal of becoming carbon-neutral by 2050.

  • How does KAYAK find such low prices on flights from Chicago 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 Chicago to Connecticut.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Connecticut

  • There are two major airports in Chicago that can get you to Connecticut. Chicago O'Hare International Airport (ORD) is located on the Northwest side of the city, while Chicago Midway International Airport (MDW) is on the Southwest side. Regardless of which Chicago airport you choose, you'll be able to use airlines like American Airlines, Delta, Frontier, Spirit Airlines, and United Airlines to get to Bradley International Airport (BDL) in Connecticut.
  • When flying from Chicago to Connecticut, you might have to make at least one stop. But before you book a flight that includes a layover, search for non-stop flights through airlines like American Airlines and United Airlines. They'll be able to help you get to Connecticut within just 2 to 2.5 hours in many cases.
  • Whether you take a direct flight from Chicago to Connecticut or book one with stops along the way, it would be worth looking into reserving a first-class seat. Some airlines, like Frontier and Spirit Airlines, won't be able to set you up with a first-class experience. But others, like American Airlines, Delta, and United Airlines, can help you get access to a comfortable seat with extra legroom and other amenities in first class.
  • If you're interested in trying to save money while flying from Chicago to Connecticut, you might want to think about packing light for it. If you're able to bring just a carry-on bag that meets your airline's requirements, you can take it on a flight for free. Otherwise, most airlines, including Delta, Frontier, and Spirit Airlines, will charge you extra baggage fees for every bag you check.
  • If you get to Chicago O'Hare International Airport early for a flight to Connecticut and have time to kill, consider visiting a lounge offered by your airline, such as American Airlines' Admirals Club or United Airlines' United Club. Chicago Midway International Airport also has a lounge called Club MDW, which is open to all passengers for a fee.

Reviews of the top 4 airlines serving from Chicago to Connecticut

 
Need help choosing which airline to fly with from Chicago 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 4201 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

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.

10.0 ExcellentDenis, Aug 2026
Read more Southwest reviews

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.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

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.

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?

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

One thing you can always count on is your AA flight getting delayed. This is not surprising when they operate these planes like a greyhound bus with wings.

The seats cushion on my seat (exit row) needs to be replaced. It felt like I was sitting on a bar rather than a seat cushion. Also, I was in the middle seat and I sat next to an oversized guy (window seat) and he took up about 25% of my space. Otherwise, the experience was good. :)

The flight was delayed by about an hour due to a maintenance issue which later then required a change of planes. The crew was great and friendly. The in-flight entertainment did not play properly on Apple Vision Pro in a Safari browser. Although the movie trailers would play fine, the actual movies themselves just had a black screen with audio. There must be something with copy protection or something that isn’t compatible with the Safari browser on Apple Vision Pro. The free inflight Wi-Fi for American Airlines Advantage members is a nice bonus. and is great that they aren’t charging extra for things that have become basic utilities in 2026, like internet access.

Good flight, regional jet so old and seats could use an upgrade

More options for your flight from Chicago to Connecticut

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