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Find cheap flights from Chicago Midway Airport to Connecticut from $59

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 6/5. 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
Sat 6/22
Sat 6/29

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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$114

Good to know

Low season

May

High season

October

Cheapest flight

$59
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 11% 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 10561 reviews
7.4Food
8.2Boarding
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

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

6.0 GoodPeter, May 2024SLC - HNL
Read more about Delta reviews

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.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

I got a one-way, last-minute nonstop flight from PDX to BWI for only $125. Yes, I got nicked $79 more for a checked suitcase and $89 more for the BIG SEAT option, but it was worth it, even with $4.50 for coffee and $10 for a snack (the latter no different than any other airline). The grand total was still less flying on any other airline.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Book cheap flights from Chicago to Connecticut

Recent round-trip flight deals

6/5Wed
1 stopFrontier
9h 46mMDW-LGA
9/21Sat
1 stopFrontier
10h 53mLGA-MDW
$114
6/5Wed
1 stopFrontier
9h 46mMDW-LGA
6/11Tue
2 stopsFrontier
16h 20mLGA-MDW
$121
9/4Wed
1 stopDelta
5h 24mMDW-EWR
9/7Sat
1 stopDelta
6h 47mEWR-MDW
$188
6/6Thu
nonstopSouthwest
2h 05mMDW-LGA
6/7Fri
nonstopSouthwest
2h 20mLGA-MDW
$188
6/25Tue
1 stopDelta
8h 09mMDW-EWR
7/30Tue
1 stopDelta
5h 04mEWR-MDW
$208
6/24Mon
nonstopSouthwest
2h 10mMDW-LGA
6/26Wed
nonstopSouthwest
2h 20mLGA-MDW
$236
6/14Fri
1 stopAllegiant Air
10h 57mMDW-EWR
6/21Fri
1 stopAllegiant Air
10h 23mEWR-MDW
$239
6/7Fri
1 stopAllegiant Air
19h 51mMDW-EWR
6/14Fri
1 stopAllegiant Air
10h 23mEWR-MDW
$269
6/7Fri
2 stops
8h 34mMDW-EWR
6/14Fri
1 stop
10h 23mEWR-MDW
$297
6/14Fri
2 stops
19h 00mMDW-EWR
6/17Mon
1 stop
10h 23mEWR-MDW
$303

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Recent one-way flight deals

6/5Wed
1 stopFrontier
9h 46mMDW-LGA
$59
6/5Wed
1 stopFrontier
9h 46mMDW-LGA
$63
7/10Wed
1 stopDelta
5h 56mMDW-EWR
$94
7/15Mon
1 stopAllegiant Air
11h 58mMDW-EWR
$103
10/15Tue
1 stopDelta
5h 06mMDW-EWR
$104
7/1Mon
1 stopAllegiant Air
11h 57mMDW-EWR
$106
6/13Thu
nonstopSouthwest
2h 05mMDW-LGA
$122
7/10Wed
nonstopSouthwest
2h 05mMDW-LGA
$127
6/8Sat
1 stopSpirit Airlines
13h 13mMDW-EWR
$173
6/8Sat
2 stopsSpirit Airlines
16h 07mMDW-LGA
$214

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Last minute flights from Midway to Connecticut

Last minute flight, train and bus deals

5/28Tue
multi-stopFrontier
31h 34mMDW-LGA
6/1Sat
multi-stopFrontier
13h 19mLGA-MDW
$257
5/28Tue
multi-stopFrontier
15h 00mMDW-LGA
5/29Wed
multi-stopFrontier
16h 53mLGA-MDW
$261
5/28Tue
multi-stopFrontier
15h 00mMDW-LGA
5/29Wed
multi-stopFrontier
16h 53mLGA-MDW
$268
5/25Sat
multi-stopDelta
4h 37mMDW-EWR
5/29Wed
multi-stopDelta
5h 06mEWR-MDW
$336
5/25Sat
multi-stopDelta
4h 24mMDW-JFK
5/29Wed
multi-stopDelta
6h 20mJFK-MDW
$371
5/28Tue
multi-stop
14h 00mMDW-EWR
6/3Mon
multi-stop
9h 48mEWR-MDW
$494
5/27Mon
multi-stop
19h 49mMDW-EWR
5/31Fri
multi-stop
9h 48mEWR-MDW
$545
5/25Sat
multi-stopPorter Airlines
6h 30mMDW-EWR
6/4Tue
multi-stopPorter Airlines
9h 27mEWR-MDW
$703
5/25Sat
multi-stopPorter Airlines
7h 30mMDW-EWR
6/4Tue
multi-stopPorter Airlines
10h 27mEWR-MDW
$708
5/25Sat
multi-stopVolaris
27h 15mMDW-JFK
5/26Sun
multi-stopVolaris
32h 17mJFK-MDW
$1,222

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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:

$84