Find flights
Deals
When to book
FAQs & Tips
Airlines

Find cheap flights from Chicago to Connecticut from $49

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 5/21. 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
Tue 6/4
Tue 6/11

Search hundreds of travel sites at once for deals on flights to Connecticut

In the last 7 days travelers have searched 43,369,418 times on KAYAK, and here is why:

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Bundle and saveSave money when you bundle your flight + hotel.

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

December

Cheapest flight

$49
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 5% 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 1537 reviews
8.0Entertainment
8.4Boarding
8.2Comfort
8.6Crew
7.9Food
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.

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.

Everything was fantastic! The crew really went above and beyond to make it a great flight. I felt cared for with EVA.

t and I Flight crew did excellent job taking care of us and feeding us and staying professional. The boarding was delayed by an hour and then extra security measures were taken. No real explanation except for they said it was more of a maintenance dey

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

Everything was good, hard to really comfortable on a flight that long.

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.

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.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

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.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

Book cheap flights from Chicago to Connecticut

Recent round-trip flight deals

5/15Wed
1 stopSpirit Airlines
7h 00mORD-BDL
6/4Tue
1 stopSpirit Airlines
5h 14mBDL-ORD
$109
5/29Wed
1 stop
24h 10mORD-BDL
6/4Tue
1 stop
5h 14mBDL-ORD
$128
5/23Thu
1 stopFrontier
5h 51mORD-BDL
5/25Sat
1 stopFrontier
28h 56mBDL-ORD
$156
7/17Wed
1 stopFrontier
24h 13mORD-BDL
7/24Wed
1 stopFrontier
28h 34mBDL-ORD
$157
5/30Thu
nonstopAmerican Airlines
2h 07mORD-BDL
6/5Wed
nonstopAmerican Airlines
2h 37mBDL-ORD
$257
5/30Thu
1 stopAmerican Airlines
4h 41mORD-BDL
6/5Wed
nonstopAmerican Airlines
2h 35mBDL-ORD
$265
5/29Wed
1 stopDelta
5h 59mMDW-BDL
6/5Wed
1 stopDelta
4h 26mBDL-MDW
$276
6/4Tue
1 stopDelta
6h 18mMDW-BDL
6/12Wed
1 stopDelta
5h 04mBDL-MDW
$302
6/5Wed
nonstopUnited Airlines
2h 16mORD-BDL
6/11Tue
nonstopUnited Airlines
2h 38mBDL-ORD
$327
8/2Fri
nonstopUnited Airlines
2h 15mORD-BDL
8/5Mon
nonstopUnited Airlines
2h 38mBDL-ORD
$334

Search by stops

Search by airline

Search by price

Recent one-way flight deals

5/21Tue
1 stopFrontier
5h 47mORD-BDL
$49
5/28Tue
1 stopFrontier
5h 47mORD-BDL
$68
5/14Tue
2 stopsSpirit Airlines
21h 01mORD-BDL
$74
5/14Tue
3 stopsSpirit Airlines
27h 22mORD-BDL
$83
5/29Wed
nonstopAmerican Airlines
2h 14mORD-BDL
$129
5/28Tue
1 stopDelta
6h 18mMDW-BDL
$138
5/25Sat
nonstopAmerican Airlines
2h 07mORD-BDL
$144
6/3Mon
1 stopDelta
3h 39mORD-BDL
$153
6/23Sun
nonstopUnited Airlines
2h 22mORD-BDL
$201
5/28Tue
2 stopsUnited Airlines
12h 23mORD-BDL
$213

Search by stops

Search by airline

Search by price

Last minute flights from Chicago to Connecticut

Last minute flight, train and bus deals

5/9Thu
multi-stopFrontier
24h 06mMDW-BDL
5/12Sun
multi-stopFrontier
15h 09mBDL-MDW
$248
5/9Thu
multi-stopFrontier
24h 11mORD-BDL
5/12Sun
multi-stopFrontier
14h 27mBDL-ORD
$268
5/7Tue
multi-stopSpirit Airlines
10h 47mORD-BDL
5/11Sat
multi-stopSpirit Airlines
5h 14mBDL-ORD
$360
5/10Fri
multi-stopSpirit Airlines
18h 54mORD-BDL
5/12Sun
multi-stopSpirit Airlines
7h 49mBDL-ORD
$391
5/7Tue
multi-stopUnited Airlines
15h 44mORD-BDL
5/8Wed
multi-stopUnited Airlines
13h 35mBDL-ORD
$760
5/10Fri
nonstopAmerican Airlines
2h 14mORD-BDL
5/12Sun
multi-stopAmerican Airlines
5h 32mBDL-ORD
$769
5/7Tue
multi-stopUnited Airlines
11h 54mORD-BDL
5/8Wed
multi-stopUnited Airlines
12h 17mBDL-ORD
$774
5/7Tue
multi-stopAmerican Airlines
6h 11mORD-BDL
5/11Sat
nonstopAmerican Airlines
2h 45mBDL-ORD
$837
5/8Wed
multi-stopDelta
6h 17mMDW-BDL
5/10Fri
multi-stopDelta
4h 26mBDL-MDW
$916
5/9Thu
multi-stopDelta
6h 41mMDW-BDL
5/12Sun
multi-stopDelta
8h 55mBDL-MDW
$1,216

Search by stops

Search by airline

Search by price

Flights to Connecticut

Return flight deals:

Connecticut - Chicago

Cabin classes:

$687
$666
$538
$144