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Find cheap flights from Chicago Midway Airport to Connecticut from $105

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Connecticut departing on 5/11. 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
Wed 5/29
Wed 6/5

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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 York1 stop$119

Good to know

Low season

April

High season

November

Cheapest flight

$105
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from Chicago Midway Airport to Hartford

FAQs - booking Connecticut flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Connecticut from Chicago Midway Airport 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 Midway 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 to Connecticut with an airline and back to Chicago Midway Airport with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago Midway 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 to Connecticut from Chicago Midway Airport 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 10% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 3 airlines serving from Midway to Connecticut

 
Need help choosing which airline to fly with from Midway 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
DeltaOverall score based on 10932 reviews
7.4food
8.2boarding
7.9comfort
8.6crew
8.0entertainment
Airline reviews

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

8.0 ExcellentCynthia, Apr 2024TYS - ATL
Read more about Delta reviews

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

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.

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. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

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.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Flight was cancelled and I had to spend the night in the airport lugging my suitcase around

Book cheap flights from Chicago to Connecticut

Recent round-trip flight deals

5/30Thu
1 stopFrontier
10h 17mMDW-BDL
6/4Tue
1 stopFrontier
6h 46mBDL-MDW
$155
5/16Thu
1 stopFrontier
10h 43mMDW-BDL
5/18Sat
1 stopFrontier
10h 42mBDL-MDW
$159
5/16Thu
1 stopFrontier
10h 43mMDW-BDL
5/18Sat
2 stopsFrontier
11h 58mBDL-MDW
$164
5/30Thu
1 stopFrontier
10h 17mMDW-BDL
6/5Wed
1 stopFrontier
14h 54mBDL-MDW
$165
5/25Sat
1 stopFrontier
23h 01mMDW-BDL
5/26Sun
1 stopFrontier
27h 08mBDL-MDW
$179
5/18Sat
1 stopFrontier
23h 01mMDW-BDL
5/20Mon
1 stopFrontier
5h 41mBDL-MDW
$181
5/28Tue
1 stopDelta
6h 18mMDW-BDL
6/4Tue
1 stopDelta
8h 15mBDL-MDW
$302
6/19Wed
1 stopDelta
4h 43mMDW-BDL
6/23Sun
1 stopDelta
4h 03mBDL-MDW
$312
5/21Tue
1 stopDelta
6h 41mMDW-BDL
5/29Wed
1 stopDelta
4h 26mBDL-MDW
$332
5/30Thu
3 stops
32h 39mMDW-BDL
6/4Tue
3 stops
25h 07mBDL-MDW
$695

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Recent one-way flight deals

5/11Sat
1 stopFrontier
13h 15mMDW-BDL
$105
6/17Mon
1 stopFrontier
22h 30mMDW-BDL
$110
7/24Wed
1 stopFrontier
29h 04mMDW-BDL
$111
5/23Thu
1 stopFrontier
10h 17mMDW-BDL
$125
5/24Fri
1 stopFrontier
28h 39mMDW-BDL
$128
5/29Wed
1 stopDelta
5h 59mMDW-BDL
$133
5/4Sat
1 stopFrontier
13h 15mMDW-BDL
$135
10/26Sat
1 stopDelta
5h 17mMDW-BDL
$148
5/28Tue
1 stopDelta
6h 18mMDW-BDL
$169
6/7Fri
2 stops
20h 53mMDW-BDL
$190

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Last minute flights from Midway to Connecticut

Last minute flight, train and bus deals

5/2Thu
multi-stopFrontier
23h 23mMDW-BDL
5/6Mon
multi-stopFrontier
13h 08mBDL-MDW
$226
5/3Fri
multi-stopFrontier
17h 28mMDW-BDL
5/6Mon
multi-stopFrontier
13h 08mBDL-MDW
$237
5/2Thu
multi-stopFrontier
23h 23mMDW-BDL
5/4Sat
multi-stopFrontier
25h 50mBDL-MDW
$260
5/2Thu
multi-stopFrontier
23h 23mMDW-BDL
5/5Sun
multi-stopFrontier
15h 09mBDL-MDW
$268
4/30Tue
multi-stopDelta
6h 14mMDW-BDL
5/4Sat
multi-stopDelta
7h 26mBDL-MDW
$838
5/1Wed
multi-stopDelta
6h 45mMDW-BDL
5/2Thu
multi-stopDelta
4h 04mBDL-MDW
$906
4/30Tue
multi-stopDelta
12h 28mMDW-BDL
5/4Sat
multi-stopDelta
7h 26mBDL-MDW
$1,019
5/1Wed
multi-stopDelta
8h 31mMDW-BDL
5/7Tue
multi-stopDelta
8h 15mBDL-MDW
$1,239
5/2Thu
multi-stopDelta
6h 28mMDW-BDL
5/7Tue
multi-stopDelta
8h 13mBDL-MDW
$1,242
5/2Thu
multi-stopDelta
8h 33mMDW-BDL
5/6Mon
multi-stopDelta
5h 07mBDL-MDW
$1,269

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Chicago Midway Airport - Connecticut Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Connecticut - Chicago Midway Airport

Cabin classes:

$144