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Midway

$51+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 12, 2025.

This Mytrip deal was found by Cheapflights users on 12/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
Wed 12/172:49 pmMDW - EWR
1 stop5h 46mFrontier
Deal found 12/9$115
This Frontier deal was found by Cheapflights users on 12/10. 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
Tue 1/136:30 pmMDW - EWR
Nonstop2h 00mFrontier
Deal found 12/10$131
This CheapOair deal was found by Cheapflights users on 12/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Sun 1/255:01 pmMDW - EWR
1 stop7h 07mFrontier
Deal found 12/10$136
This Frontier deal was found by Cheapflights users on 12/9. 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 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 1/17:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/9$138
This Super.com deal was found by Cheapflights users on 12/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Tue 12/307:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/10$140
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/1411:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 12/257:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/11$144
This Frontier deal was found by Cheapflights users on 12/8. 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.
Thu 12/2511:30 amEWR - MDW
Nonstop2h 31mFrontier
Wed 1/75:10 pmMDW - EWR
1 stop7h 00mFrontier
Deal found 12/8$151
This Priceline deal was found by Cheapflights users on 12/10. 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
Sun 1/47:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/10$155
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/1611:30 amEWR - MDW
Nonstop2h 31mFrontier
Thu 12/187:44 amMDW - EWR
Nonstop2h 01mFrontier
Deal found 12/11$156
This Frontier deal was found by Cheapflights users on 12/10. 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
Tue 1/136:30 pmMDW - EWR
Nonstop2h 00mFrontier
Deal found 12/10$157
This Delta deal was found by Cheapflights users on 12/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/2412:48 pmBDL - MDW
1 stop5h 38mDelta
Wed 12/316:08 pmMDW - BDL
1 stop4h 06mDelta
Deal found 12/10$177
This CheapOair deal was found by Cheapflights users on 12/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:59 amJFK - MDW
1 stop15h 59mFrontier
Thu 1/225:01 pmMDW - JFK
1 stop7h 02mFrontier
Deal found 12/9$197

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 12, 2025.

Round-trip from

$108
(Expedia)

One-way from

$51
(CheapOair)

Popular in

May

Cheapest in

October

Average price

$367

Good round-trip deal

$389 or less

Good one-way deal

$223 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 12, 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

Thu 1/1

11:30 am-1:01 pm

Nonstop2h 31m

Chicago Midway

Thu 1/8

12:41 pm-1:10 am

1 stop11h 29m

$120

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Fri 1/23

1:00 pm-10:19 pm

1 stop10h 19m

Chicago Midway

Mon 1/26

5:01 pm-1:03 am

1 stop7h 02m

$128

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Wed 1/14

5:55 pm-9:00 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 1/15

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Sun 1/18

7:15 pm-10:20 pm

Nonstop2h 05m

$139

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 2/26

6:15 am-7:50 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

6:05 pm-9:10 pm

Nonstop2h 05m

$149

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/23

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Mon 1/26

7:15 pm-10:20 pm

Nonstop2h 05m

$153

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/9

6:00 am-7:40 am

Nonstop2h 40m

Chicago Midway

Tue 1/13

5:55 pm-9:00 pm

Nonstop2h 05m

$153

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 1/7

6:00 am-2:06 pm

1 stop9h 06m

Chicago Midway

Thu 1/8

12:41 pm-12:59 am

1 stop11h 18m

$162

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Mon 2/9

6:30 pm-8:05 pm

Nonstop2h 35m

Chicago Midway

Wed 2/11

6:00 am-2:30 pm

1 stop7h 30m

$173

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/24

12:48 pm-5:26 pm

1 stop5h 38m

Chicago Midway

Wed 12/31

6:08 pm-11:14 pm

1 stop4h 06m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 12, 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 6, 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 31m. The time it takes to get you to your destination can typically vary by up to 3h 07m. The distance between Connecticut and Chicago Midway Airport is about 708 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 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 $133. On average you can expect to pay $361. The most popular route, (New York John F Kennedy Intl - Chicago Midway), can usually be booked for $128.

  • 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.
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
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Dallas/Fort Worth to Midway flights
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Orlando to O'Hare Intl flights
Dulles Intl to Midway flights
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Denver to Midway flights
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Minneapolis to Midway flights
Detroit to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Boston to Midway flights
Love Field to Midway flights
Hartford to O'Hare Intl flights
San Francisco to Midway flights
Portland to O'Hare Intl flights
Seattle to Midway flights
Las Vegas to O'Hare Intl flights
Miami to O'Hare Intl flights
West Palm Beach to O'Hare Intl 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 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$176Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$372FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$299Average$471FlexibilityNo cancel feeOn-time69%

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