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Midway

$55+ 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 3/12. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap 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 December 23, 2025.

This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$129
This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3011:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/22$165
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Sun 1/47:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$178
This Kiwi.com deal was found by Cheapflights users on 12/21. 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.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Tue 12/307:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$186
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:30 amEWR - MDW
Nonstop2h 31mFrontier
Mon 1/58:15 amMDW - EWR
1 stop12h 20mFrontier
Deal found 12/21$206
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:30 amEWR - MDW
Nonstop2h 31mFrontier
Sun 1/186:30 pmMDW - EWR
Nonstop2h 00mFrontier
Deal found 12/21$208
This Priceline deal was found by Cheapflights users on 12/21. 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 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/21$209
This Southwest deal was found by Cheapflights users on 12/20. 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.
Mon 12/299:50 pmLGA - MDW
Nonstop2h 25mSouthwest
Thu 1/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 12/20$213
This Southwest deal was found by Cheapflights users on 12/20. 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.
Sun 12/286:00 amLGA - MDW
Nonstop2h 30mSouthwest
Thu 1/16:00 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 12/20$223
This Southwest deal was found by Cheapflights users on 12/21. 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.
Wed 12/319:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Fri 1/28:35 amMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/21$243
This Southwest deal was found by Cheapflights users on 12/21. 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 12/279:40 pmLGA - MDW
Nonstop2h 30mSouthwest
Sat 1/175:35 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 12/21$253
This Trip.com deal was found by Cheapflights users on 12/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:20 amLGA - MDW
1 stop8h 01mFrontier
Tue 1/66:52 amMDW - LGA
1 stop8h 37mFrontier
Deal found 12/22$261

Find flight deals from Connecticut to Midway

Keep the following information in mind while searching for Connecticut to Midway flight deals. Data was last updated December 23, 2025.

Round-trip from

$110
(Expedia)

One-way from

$55
(Expedia)

Popular in

May

Cheapest in

October

Average price

$367

Good round-trip deal

$410 or less

Good one-way deal

$218 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. 10% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in December 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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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 December 23, 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

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 1/14

11:30 am-10:19 pm

1 stop11h 49m

Chicago Midway

Sun 1/18

6:30 pm-9:30 pm

Nonstop2h 00m

$110

NewarkChicago

EWR - MDW

EWRMDW

Newark

Wed 2/4

6:10 am-12:05 pm

1 stop6h 55m

Chicago Midway

Thu 2/12

12:25 pm-9:36 pm

1 stop8h 11m

$145

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Tue 2/3

6:10 am-12:05 pm

1 stop6h 55m

Chicago Midway

Mon 2/9

5:01 pm-1:03 am

1 stop7h 02m

$145

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 1/14

9:45 pm-11:15 pm

Nonstop2h 30m

Chicago Midway

Sun 1/18

6:05 am-9:10 am

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 2/10

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Wed 2/11

6:05 am-9:10 am

Nonstop2h 05m

$148

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/17

8:20 am-1:40 pm

1 stop6h 20m

Chicago Midway

Sat 1/24

5:35 pm-8:40 pm

Nonstop2h 05m

$154

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/16

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 1/12

9:45 pm-11:15 pm

Nonstop2h 30m

Chicago Midway

Mon 1/19

8:10 pm-11:10 pm

Nonstop2h 00m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

6:30 pm-8:15 pm

Nonstop2h 45m

Chicago Midway

Mon 1/19

8:10 pm-11:10 pm

Nonstop2h 00m

$157

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

6:30 pm-8:15 pm

Nonstop2h 45m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

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, August is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $137). Flying from Connecticut to Chicago Midway Airport in November is currently the most expensive (average of $311). 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 December 23, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 21% on flights from Connecticut to Chicago Midway Airport by exploring options for tickets in the evening.

What is the cheapest day to fly from Connecticut to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Midway. Price data was last updated on December 20, 2025.

Travelers seeking maximum savings on their Connecticut to Chicago Midway Airport flight should consider departing on Wednesday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 Frontier, Southwest, and Delta fly from Connecticut to Chicago Midway Airport in about 2h 30m. The time it takes to get you to your destination can typically vary by up to 9h 19m. The distance between Connecticut and Chicago Midway Airport is about 722 mi. This flight may include one or multiple stops.

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

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

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

    The cheapest flight price from Connecticut to Chicago Midway Airport is $153. On average you can expect to pay $373. The most popular route, (Newark - Chicago Midway), can usually be booked for $119.

  • 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, August is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $137). Flying from Connecticut to Chicago Midway Airport in November is currently the most expensive (average of $311). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to O'Hare Intl flights
Denver to O'Hare Intl flights
Boston to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Seattle to O'Hare Intl flights
Newark to Midway flights
Reagan-National to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Los Angeles to Midway flights
Philadelphia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Ontario to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Atlanta to Midway flights
Tampa to O'Hare Intl flights
LaGuardia to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Orlando to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Love Field to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Baltimore to Midway flights
Miami to O'Hare Intl flights
San Diego to O'Hare Intl flights
Hobby to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Hobby to Midway flights
Minneapolis to Midway flights
George Bush Intcntl to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Orlando to Midway flights
Denver to Midway flights
Dulles Intl to Midway flights
Boston to Midway flights
Portland to O'Hare Intl flights
Columbus to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Detroit to O'Hare Intl flights
George Bush Intcntl to Midway flights
San Francisco to Midway flights
Love Field to Midway flights

Top 3 airlines flying from Connecticut to Midway

Discover the top 3 airlines 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$299Average$471FlexibilityNo cancel feeOn-time69%

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