$59 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 2/16. 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

Mon, Apr 20 - Tue, May 12
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
Thu, Mar 26 - Tue, Mar 31
Frontier Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Frontier Logo
1:30 pm - 3:02 pm
EWR
-
MDW
2h 32mnonstop
$106Frontier
Tue, Apr 21 - Thu, May 14
Frontier Logo
2:20 pm - 1:16 am
MDW
-
EWR
9h 56m
1 stop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$108Frontier
Sat, Apr 18 - Wed, Apr 22
Frontier Logo
2:20 pm - 9:29 pm
MDW
-
EWR
6h 09m
1 stop
Frontier Logo
11:30 am - 1:00 pm
EWR
-
MDW
2h 30mnonstop
$110Frontier
Tue, Feb 17 - Thu, Feb 19
Southwest Logo
8:40 am - 11:50 am
MDW
-
LGA
2h 10mnonstop
Southwest Logo
6:30 pm - 8:15 pm
LGA
-
MDW
2h 45mnonstop
$117Southwest
Tue, Mar 17 - Wed, Mar 25
Multiple Airlines Logo
7:30 am - 10:30 am
MDW
-
EWR
2h 00mnonstop
Multiple Airlines Logo
5:39 pm - 10:19 pm
EWR
-
MDW
5h 40m
1 stop
$117Multiple Airlines
Sat, Feb 28 - Mon, Mar 2
Southwest Logo
10:20 am - 1:25 pm
MDW
-
LGA
2h 05mnonstop
Southwest Logo
6:00 am - 7:40 am
LGA
-
MDW
2h 40mnonstop
$125Southwest
Mon, Feb 9 - Wed, Feb 11
Multiple Airlines Logo
7:00 pm - 11:24 am
MDW
-
BDL
15h 24m
1 stop
Multiple Airlines Logo
7:20 am - 11:27 am
BDL
-
MDW
29h 07m
2 stops
$239Multiple Airlines
Wed, Feb 25 - Tue, Mar 3
Delta Logo
6:00 am - 11:58 am
MDW
-
PVD
4h 58m
1 stop
Delta Logo
5:30 am - 11:59 am
PVD
-
MDW
7h 29m
1 stop
$317Delta
Thu, Feb 26 - Sat, Feb 28
Delta Logo
6:00 am - 11:58 am
MDW
-
PVD
4h 58m
1 stop
Delta Logo
3:00 pm - 10:31 pm
PVD
-
MDW
8h 31m
1 stop
$327Delta
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 $259.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$59
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 9% 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 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 $109 one-way - $197 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 4268 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

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

Information on your arrival and departure airports

Chicago Midway Airport (MDW)