MDW

$49 Find Cheap Flights from Connecticut to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Midway departing on 7/22. 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

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Cheap Flights from Connecticut to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Connecticut to Midway 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 Connecticut to Midway

Tue, Aug 5 - Wed, Aug 6
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
Southwest Logo
7:05 pm - 10:15 pmMDW-LGA
2h 10mnonstop
$97Southwest
Find Deal
Tue, Jul 8 - Sat, Jul 12
Southwest Logo
9:35 pm - 10:55 pmLGA-MDW
2h 20mnonstop
Southwest Logo
4:25 pm - 7:35 pmMDW-LGA
2h 10mnonstop
$117Southwest
Find Deal
Sat, Sep 13 - Tue, Sep 16
Delta Logo
9:40 am - 12:32 pmEWR-MDW
3h 52m1 stop
Delta Logo
6:00 am - 12:20 pmMDW-EWR
5h 20m1 stop
$157Delta
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Tue, Jul 8 - Tue, Jul 22
Delta Logo
6:00 am - 8:44 amEWR-MDW
3h 44m1 stop
Delta Logo
6:20 pm - 11:13 pmMDW-EWR
3h 53m1 stop
$167Delta
Find Deal
Sat, Sep 20 - Tue, Sep 23
Frontier Logo
1:01 pm - 11:09 pmJFK-MDW
11h 08m1 stop
Frontier Logo
8:00 am - 7:28 amMDW-JFK
22h 28m1 stop
$182Frontier
Find Deal
Tue, Sep 9 - Wed, Sep 10
Frontier Logo
9:00 am - 10:58 pmJFK-MDW
14h 58m1 stop
Frontier Logo
8:00 am - 12:40 amMDW-JFK
15h 40m1 stop
$184Frontier
Find Deal
Sun, Jul 13 - Fri, Jul 18
Allegiant Air Logo
9:55 am - 9:41 amEWR-MDW
24h 46m1 stop
Allegiant Air Logo
10:31 am - 9:05 amMDW-EWR
21h 34m1 stop
$224Allegiant Air
Find Deal
Fri, Aug 1 - Mon, Aug 4
Allegiant Air Logo
9:55 am - 1:56 pmEWR-MDW
5h 01m1 stop
Allegiant Air Logo
1:11 pm - 9:05 amMDW-EWR
18h 54m1 stop
$232Allegiant Air
Find Deal
Thu, Jul 10 - Wed, Jul 16
Logo
10:12 am - 9:41 amEWR-MDW
24h 29m2 stops
Logo
4:27 pm - 12:05 pmMDW-EWR
18h 38m1 stop
$291
Find Deal
Tue, Jun 24 - Fri, Jun 27
Logo
11:55 am - 3:37 pmEWR-MDW
28h 42m1 stop
Logo
10:34 am - 7:00 pmMDW-EWR
31h 26m2 stops
$299
Find Deal
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Good to know

Low seasonJanuary
High seasonJuly
Cheapest flight$49
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from New York LaGuardia Airport to Chicago Midway Airport

FAQs for booking Connecticut to Chicago Midway Airport flights

  • How does KAYAK find such low prices on flights from Connecticut to Chicago Midway Airport?

    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 Connecticut to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Connecticut to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from 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 Connecticut to Chicago Midway Airport?

    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 Chicago Midway Airport with an airline and back to Connecticut with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Connecticut to Chicago Midway Airport?

    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 Chicago Midway Airport from Connecticut up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Midway

Information on your arrival and departure airports

Chicago Midway Airport (MDW)

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