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$79+ Cheap flights from Midway (MDW) to Connecticut

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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Midway to Connecticut

Keep the following information in mind while searching for Midway to Connecticut flight deals. Data was last updated July 29, 2025.

Round-trip from

$147
(Southwest)

One-way from

$79
(Southwest)

Good round-trip deal

$157 or less

Good one-way deal

$136 or less
From Chicago Midway to Connecticut
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One-way flight from Chicago Midway to Connecticut
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Price to beat on a round-trip flight from Chicago Midway to Connecticut.
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Find flight deals from Midway to Connecticut

Cheapest flights from Midway to Connecticut
Explore the most affordable flight options available from Midway to Connecticut. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 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.
Wed 9/107:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Sat 9/137:30 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 7/28$147
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/65:15 pmMDW - EWR
1 stop6h 19mFrontier
Thu 10/910:00 pmEWR - MDW
Nonstop2h 25mFrontier
Deal found 7/27$160
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 9/131:08 pmMDW - EWR
1 stop3h 30mDelta
Sat 9/209:51 amEWR - MDW
1 stop3h 37mDelta
Deal found 7/29$167
This Southwest deal was found by Cheapflights users on 7/26. 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 10/146:10 pmMDW - BDL
Nonstop2h 05mSouthwest
Sun 10/195:45 amBDL - MDW
Nonstop2h 25mSouthwest
Deal found 7/26$177
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 9/206:15 amMDW - JFK
1 stop17h 53mFrontier
Wed 9/246:15 amJFK - MDW
1 stop10h 43mFrontier
Deal found 7/27$189
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/55:15 pmMDW - LGA
1 stop5h 42mFrontier
Mon 9/811:30 amLGA - MDW
1 stop5h 30mFrontier
Deal found 7/29$195
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 8/286:17 pmMDW - BDL
1 stop4h 04mDelta
Tue 9/25:35 amBDL - MDW
1 stop4h 00mDelta
Deal found 7/28$197
This FlightHub deal was found by Cheapflights users on 7/26. 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 8/2310:51 amMDW - BDL
1 stop22h 19mFrontier
Sat 8/3011:44 amBDL - MDW
1 stop21h 38mFrontier
Deal found 7/26$215
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/305:35 pmMDW - PVD
Nonstop2h 15mSouthwest
Tue 9/26:10 pmPVD - MDW
Nonstop2h 25mSouthwest
Deal found 7/27$217
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.
Wed 12/39:30 amMDW - PVD
1 stop5h 31mDelta
Sat 12/62:10 pmPVD - MDW
1 stop8h 34mDelta
Deal found 7/29$237
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 11/151:00 pmMDW - JFK
1 stop9h 19mDelta
Thu 12/2512:55 pmJFK - MDW
1 stop4h 28mDelta
Deal found 7/28$272

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Connecticut 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 29, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Connecticut that are best for you.

Fly from

Midway

Fly to

Connecticut

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/10

7:05 pm-10:15 pm

Nonstop2h 10m

New York LaGuardia

Sat 9/13

7:30 am-8:50 am

Nonstop2h 20m

$147

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Mon 10/6

5:15 pm-12:34 am

1 stop6h 19m

Newark

Thu 10/9

10:00 pm-11:25 pm

Nonstop2h 25m

$160

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 9/13

1:08 pm-5:38 pm

1 stop3h 30m

Newark

Sat 9/20

9:51 am-12:28 pm

1 stop3h 37m

$167

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 10/14

6:10 pm-9:15 pm

Nonstop2h 05m

Hartford Bradley Intl

Sun 10/19

5:45 am-7:10 am

Nonstop2h 25m

$177

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 9/20

6:15 am-1:08 am

1 stop17h 53m

New York John F Kennedy Intl

Wed 9/24

6:15 am-3:58 pm

1 stop10h 43m

$189

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/5

5:15 pm-11:57 pm

1 stop5h 42m

New York LaGuardia

Mon 9/8

11:30 am-4:00 pm

1 stop5h 30m

$195

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 8/28

6:17 pm-11:21 pm

1 stop4h 04m

Hartford Bradley Intl

Tue 9/2

5:35 am-8:35 am

1 stop4h 00m

$197

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 8/23

10:51 am-10:10 am

1 stop22h 19m

Hartford Bradley Intl

Sat 8/30

11:44 am-8:22 am

1 stop21h 38m

$215

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Sat 8/30

5:35 pm-8:50 pm

Nonstop2h 15m

Providence-TFGreen

Tue 9/2

6:10 pm-7:35 pm

Nonstop2h 25m

$217

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Mon 9/8

6:17 pm-11:09 pm

1 stop3h 52m

Providence-TFGreen

Tue 9/9

12:45 pm-6:37 pm

1 stop6h 52m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Showing 1-10 of 26 results
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Best time to book a flight from Midway to Connecticut

Have a flexible travel schedule? Discover the best time to fly to Connecticut from Midway 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 Chicago Midway Airport to Connecticut

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

Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Connecticut (average of $287). Flying from Chicago Midway Airport to Connecticut in December is currently the most expensive (average of $351). 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 MDW to CT?

Find hourly flight availability from Midway to Connecticut. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Connecticut as you normally would.

Reviews of airlines servicing Connecticut

Get insights into the airlines that provide service to Connecticut. 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 Connecticut. Reviews last updated July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Allegiant Air from Chicago Midway Airport to Connecticut. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
702 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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 Midway to Connecticut. 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 Chicago Midway Airport to Connecticut 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 Chicago Midway Airport to Connecticut?

    While some choose either Chicago Midway - New York LaGuardia or Chicago Midway - New York John F Kennedy Intl, Chicago Midway - Newark is the most popular route from Chicago Midway Airport to Connecticut.

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

    While on average a flight from Chicago Midway Airport to Connecticut is generally $169, our data shows the cheapest flight currently is $68. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $77 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Connecticut 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 Chicago Midway Airport to Connecticut?

    Currently, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Connecticut (average of $287). Flying from Chicago Midway Airport to Connecticut in December is currently the most expensive (average of $351). 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

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Alternative routes for Midway to Connecticut

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Midway to Connecticut

Discover the top airline that operate flights from Midway to Connecticut. 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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$350FlexibilityNo cancel feeOn-time63%

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