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Find cheap flights from Chicago to Connecticut from $60

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Connecticut departing on 5/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sun 6/9
Sun 6/16

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Best Connecticut Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

New York
New Yorknonstop$50

Good to know

Low season

February

High season

November

Cheapest flight

$60
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Chicago O'Hare Airport to Hartford

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 to Connecticut from Chicago 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 to Connecticut with an airline and back to Chicago 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 to Connecticut from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Connecticut

  • Morning departure is around 21% cheaper than an evening flight, on average*.
  • 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.
See more tips
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 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.
8.3
EVA AirOverall score based on 1524 reviews
8.4Boarding
7.9Food
8.2Comfort
8.6Crew
8.0Entertainment
Airline reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

8.0 ExcellentAnonymous, Apr 2024TPE - JFK
Read more about EVA Air reviews

The type of the food requested (Asian vegetarian) was not properly met with. They have very limited snack items that may compensate for the main meals.

The quality of the food is pretty good. Thank you, EVA Air.

Fast and efficient boarding. Flight was on time. Service was very good for our long flight. First time flying with this airline and I would highly recommend.

Eva Air's Business Class is pretty decent. With the given price, I think that the food can be better.

Pleasant crew. Very long flight, a bit uncomfortable at times being seated, but not too bad.

No ice for the drinks. Only gave a half a cup of your beverage. Not enough water. I got very dehydrated.

Eva air is a good airline. The seats on the way to Taipei could have certainly been more comfortable, but all in all it was a pretty good experience.

Eva is one of the top airlines in Asia... but often are over priced. Finally found a reasonable rate.

My original flight was rescheduled & EVA did a good job rescheduling my flight & connecting flight.

Polite hard working crew. No complaints really. Meals were not to my liking.

I’ve had a couple flights this week on United that were delayed by an hour or more

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

The control panel for the seat back screen did not work at all after takeoff.

Plane was so old it had cigarette butt trays in the seat

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Flight was delayed at departure due to weather and the need for de-icing. The flight was smooth but there was a delay at arrival due to weather. We were in a hold for 20 minutes or more. The flight arrived more than 30 minutes late. Airlines have no control over the weather and I'm glad that they follow all safety procedures. Had to wait a long time for my checked luggage. Whole process was slow and the bags arrived wet due to the rain. The onboard wifi and entertainment access was spotty and the signal was dropped several times. Otherwise the crew was great and friendly. They tried to get everyone's bags stowed and seated so we could take off.

Regarding the boarding: it needs more efforts to make it more convenient

Deicing in Denver took forever and I almost missed my connection. De-ice faster! Not Americans fault.

Flight delayed then canceled! I will NEVER fly Spirit Airlines again and will tell all my friends!

Absolutely terrible. The boarding process had zero organization. Mobs of people trying to board. People were climbing over my child's stroller with her in it. No families were boarded first. Boarding was delayed with no reasoning or notification that it would be late. We were then stuck on the plane for 45 minutes after landing. Then waited over two hours for our luggage. There was zero communication with the travelers. Never have I experienced such I professionalism and disgrace of others. Extremely disappointed.

For it to have left on time! Instead of two hours early with zero notice

Flight kept delayed from morning to late afternoon so I had to make other arrangements

Crew was nice, explained emergency protocol very well. Flight took off and arrived on time. Pilot explained the small delay that occurred with docking and providing updates. I would definitely fly spirit again.

Terrible… missed our flight due to ridiculously long time to go thru baggage check-in!

The crew was not great or professional. It seemed like they didn't really want to be there. A true lack of effort for accommodating customers.

Everything was really good but the seats are not very comfortable.

I paid for WiFi, but it (WiFi) was very very slow, will never take again! Impossible open Utube 😤😤😤

I had no legroom, although I paid for extra legroom. I could barely put my bag in front of my feet and under the seat. The Wi-Fi was horrible. In fact the flight attendant said that they had to reboot it and see if it was going to work and never did.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

I didn't get to do this flight l, hard to review

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Book cheap flights from Chicago to Connecticut

Recent round-trip flight deals

6/5Wed
1 stopSpirit Airlines
5h 26mORD-BDL
6/11Tue
1 stopSpirit Airlines
10h 07mBDL-ORD
$130
5/30Thu
1 stopSpirit Airlines
4h 43mORD-BDL
6/4Tue
1 stopSpirit Airlines
5h 14mBDL-ORD
$136
5/31Fri
1 stopFrontier
28h 39mMDW-BDL
6/4Tue
1 stopFrontier
6h 46mBDL-MDW
$158
5/31Fri
1 stopFrontier
28h 39mMDW-BDL
6/9Sun
1 stopFrontier
9h 06mBDL-MDW
$161
6/12Wed
nonstopUnited Airlines
2h 15mORD-BDL
6/26Wed
nonstopUnited Airlines
2h 38mBDL-ORD
$257
6/4Tue
nonstopAmerican Airlines
2h 07mORD-BDL
6/4Tue
1 stopAmerican Airlines
4h 44mBDL-ORD
$265
6/1Sat
nonstopAmerican Airlines
2h 14mORD-BDL
6/5Wed
nonstopAmerican Airlines
2h 35mBDL-ORD
$272
6/5Wed
1 stopDelta
8h 15mMDW-BDL
6/11Tue
1 stopDelta
8h 18mBDL-MDW
$276
8/17Sat
1 stopDelta
4h 36mMDW-BDL
11/20Wed
1 stopDelta
3h 56mBDL-MDW
$291
6/18Tue
nonstopUnited Airlines
2h 17mORD-BDL
6/24Mon
nonstopUnited Airlines
2h 36mBDL-ORD
$303

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Recent one-way flight deals

5/18Sat
1 stopSpirit Airlines
4h 43mORD-BDL
$60
6/11Tue
1 stopSpirit Airlines
4h 53mORD-BDL
$66
5/16Thu
1 stopFrontier
5h 51mORD-BDL
$75
5/28Tue
1 stopFrontier
5h 47mORD-BDL
$79
7/2Tue
1 stopDelta
4h 45mMDW-BDL
$138
6/20Thu
nonstopAmerican Airlines
2h 22mORD-BDL
$144
6/11Tue
nonstopUnited Airlines
2h 17mORD-BDL
$164
6/23Sun
nonstopAmerican Airlines
2h 22mORD-BDL
$175
6/8Sat
nonstopUnited Airlines
2h 15mORD-BDL
$187
5/28Tue
1 stopDelta
5h 04mMDW-BDL
$265

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Last minute flights from Chicago to Connecticut

Last minute flight, train and bus deals

5/15Wed
multi-stop
26h 18mORD-BDL
5/16Thu
multi-stop
28h 57mBDL-ORD
$200
5/14Tue
multi-stopFrontier
15h 21mORD-BDL
5/16Thu
multi-stopFrontier
28h 57mBDL-ORD
$262
5/11Sat
multi-stopSpirit Airlines
4h 43mORD-BDL
5/13Mon
multi-stopSpirit Airlines
5h 14mBDL-ORD
$461
5/14Tue
multi-stopSpirit Airlines
4h 45mORD-BDL
5/15Wed
multi-stopSpirit Airlines
5h 14mBDL-ORD
$481
5/14Tue
multi-stopUnited Airlines
7h 04mORD-BDL
5/15Wed
nonstopUnited Airlines
2h 37mBDL-ORD
$729
5/14Tue
multi-stopAmerican Airlines
9h 34mORD-BDL
5/16Thu
nonstopAmerican Airlines
2h 41mBDL-ORD
$771
5/14Tue
nonstopAmerican Airlines
2h 14mORD-BDL
5/16Thu
nonstopAmerican Airlines
2h 41mBDL-ORD
$824
5/14Tue
nonstopUnited Airlines
2h 17mORD-BDL
5/16Thu
nonstopUnited Airlines
2h 40mBDL-ORD
$829
5/14Tue
multi-stopDelta
6h 18mMDW-BDL
5/16Thu
multi-stopDelta
4h 26mBDL-MDW
$848
5/14Tue
multi-stopDelta
6h 17mMDW-BDL
5/15Wed
multi-stopDelta
3h 58mBDL-MDW
$916

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Flights to Connecticut

Return flight deals:

Connecticut - Chicago

Cabin classes:

$687
$666
$538
$135