$64 Find Cheap Flights from Chicago Midway Airport to Connecticut

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 1/28. 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
1 adult, Economy, 0 bags

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Connecticut, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Connecticut, as well as popular online travel agencies
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Flight Deals

Book Cheap Midway to Connecticut Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Midway to Connecticut that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Midway to Connecticut

Tue, Jan 13 - Wed, Jan 28
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:10 am - 12:05 pm
EWR
-
MDW
6h 55m1 stop
$104Frontier
Sun, Jan 18 - Thu, Jan 22
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 11:45 am
EWR
-
MDW
6h 45m1 stop
$115Frontier
Thu, Jan 15 - Thu, Jan 22
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 11:45 am
EWR
-
MDW
6h 45m1 stop
$117Frontier
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
8:19 pm - 2:50 pm
MDW
-
EWR
17h 31m1 stop
Multiple Airlines Logo
10:30 pm - 12:02 am
EWR
-
MDW
2h 32mnonstop
$118Multiple Airlines
Tue, Jan 13 - Tue, Jan 20
Frontier Logo
6:30 pm - 9:30 pm
MDW
-
EWR
2h 00mnonstop
Frontier Logo
6:00 am - 12:05 pm
EWR
-
MDW
7h 05m1 stop
$121Frontier
Tue, Jan 13 - Tue, Jan 20
Southwest Logo
5:55 pm - 9:00 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$139Southwest
Sat, Jan 24 - Tue, Jan 27
Southwest Logo
5:35 pm - 8:40 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$148Southwest
Sat, Jan 17 - Sun, Jan 18
Delta Logo
11:45 am - 8:08 pm
MDW
-
BDL
7h 23m1 stop
Delta Logo
5:40 am - 8:52 am
BDL
-
MDW
4h 12m1 stop
$177Delta
Fri, Jan 23 - Sun, Jan 25
Multiple Airlines Logo
1:00 pm - 11:16 pm
MDW
-
BDL
9h 16m2 stops
Multiple Airlines Logo
12:11 pm - 10:19 pm
BDL
-
MDW
11h 08m1 stop
$244Multiple Airlines
Wed, Feb 18 - Sat, Feb 21
Delta Logo
6:17 pm - 11:39 pm
MDW
-
BDL
4h 22m1 stop
Delta Logo
5:30 am - 8:53 am
BDL
-
MDW
4h 23m1 stop
$245Delta
Booking Insights

KAYAK's insights & trends for Midway to Connecticut flights

Get data-powered insights and trends into flights from Midway to Connecticut to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago Midway Airport to Connecticut flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Connecticut from Chicago Midway Airport found in the last 72 hours was to New Haven, at $82 round-trip. The most popular route is from Chicago Midway Airport (MDW) to Hartford (BDL), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $157.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$64
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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 from Chicago Midway Airport to Connecticut 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 from Chicago Midway Airport to Connecticut with an airline and back 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 from Chicago Midway Airport to Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Connecticut

  • Looking for a cheap flight? 25% of our users found tickets from Chicago Midway Airport to the following destinations at these prices or less: Newark $67 one-way - $62 round-trip

Reviews of the top airline flying from Midway to Connecticut

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Connecticut. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
7.9
SouthwestOverall score based on 4250 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything you need to know for your flight from Midway to Connecticut

Information on your arrival and departure airports

Chicago Midway Airport (MDW)