$75 Find Cheap Flights from Chicago O'Hare Airport to Connecticut - Compare and Save

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Cheap Flights from O'Hare Intl to Connecticut

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
New Haven
2h 20mNonstop
from $135per person
New York
2h 10mNonstop
from $229per person
Newark
2h 06mNonstop
from $238per person
Providence
2h 31mNonstop
from $275per person
Hartford
2h 19mNonstop
from $277per person
Booking Insights

KAYAK's insights & trends for O'Hare Intl to Connecticut flights

Get data-powered insights and trends into flights from O'Hare Intl 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 O'Hare Intl Airport to Connecticut?

Flight prices are below average for this route right now.

Flights to Connecticut from Chicago O'Hare Intl Airport usually cost between $300 and $518 in December.
The lowest price found in the past 5 days was $277 on Delta (Dec 15-Jan 5).

What is the cheapest Chicago O'Hare Intl Airport to Connecticut flight route?

The cheapest ticket to Connecticut from Chicago O'Hare Intl Airport 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 $315.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Connecticut?

No, with an average price for the route of $333, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Connecticut?

The cheapest month for flights from Chicago O'Hare Intl Airport to Connecticut is December, when tickets cost $301 (return) on average. On the other hand, the most expensive months are July and January, when the average cost of round-trip tickets is $527 and $490 respectively.

Good to know

Low season

April

Cheapest flight

$75
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Chicago to New Haven

FAQs - booking Connecticut flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport 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 O'Hare Airport to Connecticut.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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 O'Hare Airport 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

  • Looking for a cheap flight? 25% of our users found tickets from Chicago O'Hare Airport to the following destinations at these prices or less: Newark $181 one-way - $299 round-trip; New York $160 one-way - $286 round-trip

Reviews of the top 3 airlines serving from O'Hare Intl to Connecticut

 
Need help choosing which airline to fly with from O'Hare Intl 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.
7.5
Avelo AirlinesOverall score based on 85 reviews
8.2Crew
5.0Entertainment
5.1Food
7.7Boarding
7.1Comfort
Airline reviews

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!

8.0 ExcellentMaurice, Aug 2026
Read more Avelo Airlines reviews

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.

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

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.

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?

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

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. :)

More options for your flight from O'Hare Intl to Connecticut

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