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Find cheap flights from Chicago Midway Airport to Connecticut from $62

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 8/21. 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
Fri 7/5
Fri 7/12

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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$112

Good to know

Low season

May

High season

October

Cheapest flight

$62
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Chicago Midway Airport to New York LaGuardia Airport

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 7% 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 10377 reviews
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
8.6Crew
Airline reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

2.0 MediocreFelipe, Jun 2024DTW - SAN
Read more about Delta reviews

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

There was plenty of overhead room but half of the passengers were told they had to check their carryon bags. My partner and I checked in as early as possible and our seats were split across the aisle.

Friendly flight attendants. Comfort plus seats were very comfortable and had lots of leg room. 10A and 10 B.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Flight was good and clean but delayed over an hour on the return flight.

The non stop flight and able to go into Atlantic City airport. They could lower the prices. It starts out low but then if you want to bring luggage and pick your seat the price goes up quite a bit.

Flight got diwngraded last minute and left us stranded. I was told I’ll be given credit for my luggage and seat upgrades but haven’t got anything yet

We can’t predict circumstances like this ahead of time, but I give your staff a hats off for immediately giving us updated informations.

It was nice! There was a very unhappy child in front of us and the flight attendant did a great job calming the child. I was impressed.

The plane was not on time for boarding or departure or arrivals.

EVERYTHING WAS WONDERFUL HOSPITALITY THE HELP.THE SEATING FRIENDLY ALWAYS HAVE A GOOD RIDE NOT ONE BAD EXPERIENCE WITH THEM

This was the smoothest flight I have had in awhile. I was also offered an exit row seat for a great upgrade cost and was able to sleep almost thr whole flight due to comfort and a smooth flight. We left on time and arrived on time.

No food not even water offered unless you buy it and no usb in the seat but other than that everything was good

Because our flight from marsh Harbor to Fort Lauderdale was over three hours delayed it caused us to miss our flight in Fort Lauderdale. Because we missed that flight, it cost us nearly $100 apiece for four different travelers which totaled nearly $400. We are seeking a reimbursement for the flight that we missed in Fort Lauderdale Florida.

The agent at check-in was strident, unwelcoming, and condescending to customers ahead of me.

Flight was delay 9hrs and nothing was provided at airport, had to go and get a room to sleep in, paid for Uber back and fort with no offers until we landed back home a 1hr later for a $75 voucher for a future flight.

Didn't like anything..entire crew was very rude to everyone on the flight. Plane old and the trays fall down on you the while time you're flying. Charged more for a carry on bag than for the plane ticket itself. Did make it from point a to point b, but worth the extra money to fly with another airline

9 hours of delay!! Was not able to check my luggage that I paid for!!!

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Book cheap flights from Chicago to Connecticut

Recent round-trip flight deals

9/10Tue
1 stopFrontier
11h 22mMDW-LGA
9/17Tue
1 stopFrontier
5h 29mLGA-MDW
$112
9/4Wed
1 stopFrontier
13h 54mMDW-LGA
9/6Fri
1 stopFrontier
5h 29mLGA-MDW
$113
9/7Sat
1 stopDelta
5h 29mMDW-EWR
9/11Wed
1 stopDelta
5h 04mEWR-MDW
$156
10/12Sat
1 stopDelta
4h 09mMDW-EWR
10/15Tue
1 stopDelta
5h 03mEWR-MDW
$186
6/17Mon
nonstopSouthwest
2h 05mMDW-LGA
6/22Sat
nonstopSouthwest
2h 30mLGA-MDW
$235
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/19Fri
1 stopAllegiant Air
10h 22mEWR-MDW
$238
6/17Mon
nonstopSouthwest
2h 05mMDW-LGA
6/20Thu
nonstopSouthwest
2h 25mLGA-MDW
$239
6/24Mon
1 stopAllegiant Air
11h 57mMDW-EWR
7/1Mon
1 stopAllegiant Air
10h 23mEWR-MDW
$260
7/1Mon
2 stops
26h 26mMDW-EWR
7/8Mon
1 stop
10h 22mEWR-MDW
$295
6/17Mon
3 stops
23h 53mMDW-EWR
6/21Fri
1 stop
10h 23mEWR-MDW
$298

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Recent one-way flight deals

8/21Wed
1 stopFrontier
10h 03mMDW-LGA
$62
9/11Wed
1 stopFrontier
10h 03mMDW-LGA
$63
8/13Tue
1 stopDelta
5h 06mMDW-EWR
$78
9/9Mon
1 stopDelta
6h 01mMDW-EWR
$89
6/14Fri
1 stopAllegiant Air
19h 51mMDW-EWR
$101
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$106
7/8Mon
nonstopSouthwest
2h 10mMDW-LGA
$122
7/8Mon
2 stopsSouthwest
11h 55mMDW-LGA
$142
6/14Fri
2 stops
14h 05mMDW-EWR
$149
6/17Mon
2 stops
10h 39mMDW-EWR
$152

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Last minute flights from Midway to Connecticut

Last minute flight, train and bus deals

6/8Sat
multi-stopFrontier
22h 34mMDW-LGA
6/11Tue
multi-stopFrontier
6h 07mLGA-MDW
$211
6/8Sat
multi-stopFrontier
22h 34mMDW-LGA
6/12Wed
multi-stopFrontier
17h 58mLGA-MDW
$212
6/10Mon
nonstopSouthwest
2h 10mMDW-LGA
6/11Tue
nonstopSouthwest
2h 25mLGA-MDW
$326
6/10Mon
multi-stopSouthwest
4h 25mMDW-LGA
6/12Wed
nonstopSouthwest
2h 35mLGA-MDW
$335
6/7Fri
multi-stopAllegiant Air
11h 31mMDW-EWR
6/14Fri
multi-stopAllegiant Air
10h 23mEWR-MDW
$361
6/10Mon
multi-stopDelta
4h 41mMDW-JFK
6/17Mon
multi-stopDelta
5h 05mJFK-MDW
$376
6/8Sat
multi-stopDelta
6h 02mMDW-EWR
6/12Wed
multi-stopDelta
3h 43mEWR-MDW
$397
6/9Sun
multi-stop
26h 14mMDW-PVD
6/15Sat
multi-stop
15h 11mPVD-MDW
$399
6/7Fri
multi-stopAllegiant Air
19h 51mMDW-EWR
6/10Mon
multi-stopAllegiant Air
9h 49mEWR-MDW
$442
6/9Sun
multi-stop
28h 21mMDW-EWR
6/28Fri
multi-stop
10h 23mEWR-MDW
$504

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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:

$82