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$70+ Cheap flights from Connecticut to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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Cheap flight deals from Connecticut to Midway

Keep the following information in mind while searching for Connecticut to Midway flight deals. Data was last updated September 16, 2025.

Round-trip from

$137
(Southwest)

One-way from

$70
(Southwest)

Popular in

April

Cheapest in

August

Average price

$317

Good round-trip deal

$314 or less

Good one-way deal

$170 or less
From Connecticut to Chicago Midway
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One-way flight from Connecticut to Chicago Midway
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Highest demand for flights based on searches. 5% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Connecticut to Chicago Midway.
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Price to beat on a one-way flight from Connecticut to Chicago Midway.
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Find flight deals from Connecticut to Midway

Cheapest flights from Connecticut to Midway
Explore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 16, 2025.

This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:05 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 10/75:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/15$137
This SmartFares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/76:30 amLGA - MDW
1 stop8h 08mFrontier
Wed 10/88:05 amMDW - LGA
1 stop7h 24mFrontier
Deal found 9/14$138
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:29 amLGA - MDW
1 stop6h 09mFrontier
Tue 11/41:56 pmMDW - LGA
1 stop8h 31mFrontier
Deal found 9/14$141
This Southwest deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:15 amLGA - MDW
Nonstop2h 25mSouthwest
Tue 11/47:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/16$142
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:30 pmLGA - MDW
1 stop6h 40mFrontier
Sun 11/1612:30 pmMDW - LGA
1 stop8h 30mFrontier
Deal found 9/14$143
This Gotogate deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/11:20 pmLGA - MDW
1 stop6h 19mFrontier
Sun 11/211:21 amMDW - LGA
1 stop8h 43mFrontier
Deal found 9/13$144
This Flightnetwork deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/266:30 amLGA - MDW
1 stop10h 30mFrontier
Sat 9/2711:23 amMDW - LGA
1 stop7h 39mFrontier
Deal found 9/14$145
This Booking.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:25 amJFK - MDW
1 stop6h 13mFrontier
Wed 11/52:06 pmMDW - JFK
1 stop9h 27mFrontier
Deal found 9/15$146
This Booking.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:55 pmLGA - MDW
1 stop13h 21mFrontier
Sun 10/2611:57 amMDW - LGA
1 stop27h 00mFrontier
Deal found 9/16$146
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/231:01 pmJFK - MDW
1 stop8h 20mFrontier
Sun 10/269:26 pmMDW - JFK
1 stop9h 02mFrontier
Deal found 9/14$147
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/18:15 amLGA - MDW
Nonstop2h 25mSouthwest
Mon 11/37:15 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 9/15$147
This Booking.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/19:00 amJFK - MDW
1 stop10h 39mFrontier
Mon 11/31:37 pmMDW - JFK
1 stop9h 56mFrontier
Deal found 9/14$148

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.

Fly from

Connecticut

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/28

9:45 pm-11:10 pm

Nonstop2h 25m

Chicago Midway

Wed 11/5

8:25 am-11:30 am

Nonstop2h 05m

$137

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 12/5

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 12/10

7:15 pm-10:20 pm

Nonstop2h 05m

$142

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Mon 10/27

1:01 pm-11:46 pm

1 stop11h 45m

Chicago Midway

Wed 10/29

2:06 pm-12:33 am

1 stop9h 27m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/1

9:00 am-6:39 pm

1 stop10h 39m

Chicago Midway

Mon 11/3

1:37 pm-12:33 am

1 stop9h 56m

$147

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 10/3

9:00 am-4:00 pm

1 stop8h 00m

Chicago Midway

Mon 10/6

5:33 pm-1:08 am

1 stop6h 35m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 10/7

2:00 pm-3:20 pm

Nonstop2h 20m

Chicago Midway

Wed 10/8

5:55 pm-11:10 pm

1 stop4h 15m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 11/1

8:15 am-9:40 am

Nonstop2h 25m

Chicago Midway

Mon 11/3

7:15 pm-10:20 pm

Nonstop2h 05m

$147

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 10/1

9:35 pm-10:55 pm

Nonstop2h 20m

Chicago Midway

Tue 10/7

5:55 pm-9:00 pm

Nonstop2h 05m

$152

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/1

9:55 pm-11:20 pm

Nonstop2h 25m

Chicago Midway

Wed 1/7

1:25 pm-11:15 pm

2 stops8h 50m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 11/13

12:40 pm-5:25 pm

1 stop5h 45m

Chicago Midway

Sun 11/16

6:10 am-9:15 am

Nonstop2h 05m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to Chicago Midway Airport

What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $160). Flying from Connecticut to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CT to MDW?

Find hourly flight availability from Connecticut to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 16, 2025.

When flying from Connecticut to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Chicago Midway Airport?

    Airlines like Southwest, Frontier, and Delta fly from Connecticut to Chicago Midway Airport in about 2h 25m. The time it takes to get you to your destination can typically vary by up to 9h 20m. The distance between Connecticut and Chicago Midway Airport is about 722 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Connecticut to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $70 on Southwest. Other airlines that offer cheap prices include Frontier from $82 and Delta from $89 one-way.

  • What are the most popular routes from Connecticut to Chicago Midway Airport?

    The most popular flight routes from Connecticut to Chicago Midway Airport are New York John F Kennedy Intl - Chicago Midway, New York LaGuardia - Chicago Midway and Newark - Chicago Midway.

  • What are the cheapest flights from Connecticut to Chicago Midway Airport?

    The cheapest flight price from Connecticut to Chicago Midway Airport is $104. On average you can expect to pay $328. The most popular route, (New York John F Kennedy Intl - Chicago Midway), can usually be booked for $146.

  • Can I find deals for flights from Connecticut to Midway that include hotel bookings?

    Yes. In addition to deals on Connecticut to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Midway.

  • Can I find deals for business class flights from Connecticut to Midway?

    Yes. Cheapflights offers flight deals from Connecticut to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $160). Flying from Connecticut to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Connecticut to Midway

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Philadelphia to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Boston to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Ontario to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
LaGuardia to Midway flights
Atlanta to Midway flights
Newark to Midway flights
Los Angeles to Midway flights
Dulles Intl to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Austin to O'Hare Intl flights
San Francisco to Midway flights
Raleigh to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Philadelphia to Midway flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Portland to O'Hare Intl flights
Burbank to O'Hare Intl flights
Hobby to O'Hare Intl flights
Providence to O'Hare Intl flights
Seattle to Midway flights
Reagan-National to Midway flights
Miami to O'Hare Intl flights
Hartford to O'Hare Intl flights
Denver to Midway flights
Cleveland to O'Hare Intl flights
Love Field to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
San Jose to O'Hare Intl flights
Minneapolis to Midway flights
San Diego to O'Hare Intl flights
Boston to Midway flights
Orlando to O'Hare Intl flights

Top airline flying from Connecticut to Midway

Discover the top airline that operate flights from Connecticut to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$177Average$384FlexibilityNo cancel feeOn-time63%

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