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Midway

$79+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$152
(Southwest)

One-way from

$79
(Southwest)

Good round-trip deal

$271 or less

Good one-way deal

$137 or less
From Connecticut to Chicago Midway
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One-way flight from Connecticut to Chicago Midway
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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 July 30, 2025.

This Southwest deal was found by Cheapflights users on 7/28. 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 9/29:35 pmLGA - MDW
Nonstop2h 20mSouthwest
Thu 9/48:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 7/28$152
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/209:51 amEWR - MDW
1 stop3h 37mDelta
Tue 9/2310:35 amMDW - EWR
1 stop5h 16mDelta
Deal found 7/28$167
This Frontier deal was found by Cheapflights users on 7/28. 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 11/211:00 amEWR - MDW
1 stop8h 18mFrontier
Thu 11/135:56 pmMDW - EWR
Nonstop2h 04mFrontier
Deal found 7/28$170
This Southwest deal was found by Cheapflights users on 7/29. 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 8/195:20 pmBDL - MDW
Nonstop2h 20mSouthwest
Wed 9/36:10 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 7/29$187
This eDestinos deal was found by Cheapflights users on 7/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/11:01 pmJFK - MDW
1 stop11h 08mFrontier
Wed 11/58:00 amMDW - JFK
1 stop15h 40mFrontier
Deal found 7/27$196
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 9/1211:30 amLGA - MDW
1 stop5h 30mFrontier
Mon 9/155:15 pmMDW - LGA
1 stop5h 42mFrontier
Deal found 7/28$196
This Delta deal was found by Cheapflights users on 7/28. 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.
Thu 8/215:35 amBDL - MDW
1 stop4h 00mDelta
Tue 8/261:08 pmMDW - BDL
1 stop3h 38mDelta
Deal found 7/28$197
This FlightHub deal was found by Cheapflights users on 7/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/912:27 pmBDL - MDW
1 stop11h 06mFrontier
Mon 8/118:35 amMDW - BDL
1 stop10h 33mFrontier
Deal found 7/28$215
This Southwest deal was found by Cheapflights users on 7/30. 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 8/2612:55 pmPVD - MDW
Nonstop2h 30mSouthwest
Sat 8/305:35 pmMDW - PVD
Nonstop2h 15mSouthwest
Deal found 7/30$217
This Delta deal was found by Cheapflights users on 7/28. 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 9/37:50 amPVD - MDW
1 stop6h 13mDelta
Sat 9/204:25 pmMDW - PVD
1 stop6h 34mDelta
Deal found 7/28$237
This Delta deal was found by Cheapflights users on 7/29. 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.
Sat 8/239:35 pmJFK - MDW
1 stop12h 00mDelta
Wed 8/271:08 pmMDW - JFK
1 stop9h 30mDelta
Deal found 7/29$252

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 July 30, 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 9/2

9:35 pm-10:55 pm

Nonstop2h 20m

Chicago Midway

Thu 9/4

8:15 pm-11:25 pm

Nonstop2h 10m

$152

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 9/20

9:51 am-12:28 pm

1 stop3h 37m

Chicago Midway

Tue 9/23

10:35 am-4:51 pm

1 stop5h 16m

$167

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sun 11/2

11:00 am-6:18 pm

1 stop8h 18m

Chicago Midway

Thu 11/13

5:56 pm-9:00 pm

Nonstop2h 04m

$170

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 8/19

5:20 pm-6:40 pm

Nonstop2h 20m

Chicago Midway

Wed 9/3

6:10 pm-9:20 pm

Nonstop2h 10m

$187

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/1

1:01 pm-11:09 pm

1 stop11h 08m

Chicago Midway

Wed 11/5

8:00 am-12:40 am

1 stop15h 40m

$196

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 9/12

11:30 am-4:00 pm

1 stop5h 30m

Chicago Midway

Mon 9/15

5:15 pm-11:57 pm

1 stop5h 42m

$196

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 8/21

5:35 am-8:35 am

1 stop4h 00m

Chicago Midway

Tue 8/26

1:08 pm-5:46 pm

1 stop3h 38m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 8/9

12:27 pm-10:33 pm

1 stop11h 06m

Chicago Midway

Mon 8/11

8:35 am-8:08 pm

1 stop10h 33m

$215

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Tue 8/26

12:55 pm-2:25 pm

Nonstop2h 30m

Chicago Midway

Sat 8/30

5:35 pm-8:50 pm

Nonstop2h 15m

$217

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Wed 9/3

7:50 am-1:03 pm

1 stop6h 13m

Chicago Midway

Sat 9/20

4:25 pm-11:59 pm

1 stop6h 34m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 27 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 July 30, 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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 30, 2025.
Read through reviews of airlines operating flights from Connecticut to Chicago Midway Airport, such as Southwest, Delta, and Allegiant Air. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Frontier
5.9
Fair
3,237 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

  • 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 $79 on Southwest. Other airlines that offer cheap prices include Delta from $84 and Frontier from $85 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 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 $68. On average you can expect to pay $286. The most popular route, (Newark - Chicago Midway), can usually be booked for $104.

  • 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
Valparaiso
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.
Dallas/Fort Worth to O'Hare Intl flights
Newark to O'Hare Intl flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Seattle to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Boston to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Baltimore to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
Philadelphia to O'Hare Intl flights
LaGuardia to Midway flights
Ontario to O'Hare Intl flights
Austin to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Dulles Intl to Midway flights
Atlanta to Midway flights
Sky Harbor Intl to O'Hare Intl flights
Denver to O'Hare Intl flights
Raleigh to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Baltimore to Midway flights
Hobby to Midway flights
Fort Lauderdale to O'Hare Intl flights
Love Field to O'Hare Intl flights
Burbank to O'Hare Intl flights
Miami to O'Hare Intl flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
San Diego to O'Hare Intl flights
Hobby to O'Hare Intl flights
San Jose to O'Hare Intl flights
Portland to O'Hare Intl flights
Los Angeles to Midway flights
Reagan-National to Midway flights
Minneapolis to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Oakland to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Minneapolis to Midway flights
Hartford 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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$167FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$176Average$276FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$362FlexibilityNo cancel feeOn-time63%

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