$58 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 4/16. 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, Apr 14 - Fri, Apr 17
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$102Frontier
Tue, Apr 14 - Thu, Apr 16
Frontier Logo
2:15 pm - 1:16 am
MDW
-
EWR
10h 01m
1 stop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$103Frontier
Tue, Apr 21 - Fri, Apr 24
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$104Frontier
Fri, Apr 17 - Sat, Apr 18
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$105Frontier
Wed, Apr 15 - Mon, Apr 20
Frontier Logo
7:30 am - 10:38 am
MDW
-
EWR
2h 08mnonstop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$106Frontier
Fri, Apr 10 - Wed, Jun 3
Southwest Logo
8:10 am - 11:15 am
MDW
-
LGA
2h 05mnonstop
Southwest Logo
9:30 pm - 11:00 pm
LGA
-
MDW
2h 30mnonstop
$177Southwest
Mon, May 4 - Wed, May 6
Multiple Airlines Logo
2:15 pm - 8:59 pm
MDW
-
LGA
5h 44m
1 stop
Multiple Airlines Logo
5:45 am - 2:12 pm
LGA
-
MDW
9h 27m
1 stop
$187Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
1:15 pm - 4:25 pm
MDW
-
PVD
2h 10mnonstop
Southwest Logo
12:45 pm - 2:20 pm
PVD
-
MDW
2h 35mnonstop
$257Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
1:00 pm - 7:00 pm
MDW
-
PVD
5h 00m
1 stop
Southwest Logo
6:10 pm - 7:40 pm
PVD
-
MDW
2h 30mnonstop
$267Southwest
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
7:45 am - 1:50 pm
MDW
-
PVD
5h 05m
2 stops
Southwest Logo
12:45 pm - 2:20 pm
PVD
-
MDW
2h 35mnonstop
$268Southwest
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 $413.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$58
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Chicago Midway Airport to Newark Liberty 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: New York $147 one-way - $241 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.
8.0
SouthwestOverall score based on 4320 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

We had a 5 hour delay on the tarmac in Baltimore

2.0 MediocreDavid, Mar 2026
ALB - BWI
Read more Southwest reviews

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)