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$61+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
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 October 29, 2025.

Round-trip from

$110
(Frontier)

One-way from

$61
(Frontier)

Popular in

December

Cheapest in

August

Average price

$353

Good round-trip deal

$240 or less

Good one-way deal

$206 or less
From Chicago Midway to Connecticut
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One-way flight from Chicago Midway to Connecticut
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Highest demand for flights based on searches. 10% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Chicago Midway to Connecticut.
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Price to beat on a one-way 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 October 29, 2025.

This Frontier deal was found by Cheapflights users on 10/28. 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.
Tue 11/111:56 pmMDW - LGA
1 stop8h 31mFrontier
Tue 11/186:24 amLGA - MDW
1 stop6h 14mFrontier
Deal found 10/28$110
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:56 pmMDW - JFK
1 stop9h 37mFrontier
Thu 11/1310:00 amJFK - MDW
1 stop9h 39mFrontier
Deal found 10/28$110
This Frontier deal was found by Cheapflights users on 10/28. 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.
Tue 11/111:56 pmMDW - LGA
1 stop8h 31mFrontier
Thu 11/1312:30 pmLGA - MDW
1 stop7h 09mFrontier
Deal found 10/28$111
This Booking.com deal was found by Cheapflights users on 10/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:06 pmMDW - JFK
1 stop19h 54mFrontier
Wed 11/124:00 pmJFK - MDW
1 stop20h 30mFrontier
Deal found 10/27$111
This Trip.com deal was found by Cheapflights users on 10/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/122:06 pmMDW - LGA
1 stop8h 21mFrontier
Sat 11/151:20 pmLGA - MDW
1 stop6h 19mFrontier
Deal found 10/27$116
This Mytrip deal was found by Cheapflights users on 10/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:06 pmMDW - JFK
1 stop19h 54mFrontier
Thu 11/131:05 pmJFK - MDW
1 stop8h 39mFrontier
Deal found 10/27$121
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/176:15 amMDW - LGA
1 stop12h 15mFrontier
Wed 11/196:24 amLGA - MDW
1 stop7h 17mFrontier
Deal found 10/28$122
This Trip.com deal was found by Cheapflights users on 10/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:37 pmMDW - JFK
1 stop9h 56mFrontier
Wed 11/196:20 amJFK - MDW
1 stop7h 21mFrontier
Deal found 10/28$122
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:05 amMDW - JFK
1 stop17h 19mFrontier
Thu 12/41:00 pmJFK - MDW
1 stop6h 08mFrontier
Deal found 10/28$123
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - LGA
1 stop8h 50mFrontier
Wed 11/196:24 amLGA - MDW
1 stop7h 17mFrontier
Deal found 10/29$124
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/151:37 pmMDW - JFK
1 stop9h 56mFrontier
Wed 11/196:20 amJFK - MDW
1 stop7h 21mFrontier
Deal found 10/29$124
This Priceline deal was found by Cheapflights users on 10/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/46:26 pmMDW - EWR
Nonstop2h 04mFrontier
Wed 11/56:00 amEWR - MDW
1 stop7h 41mFrontier
Deal found 10/28$127

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 October 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 - JFK

MDWJFK

Chicago Midway

Mon 11/17

1:37 pm-12:33 am

1 stop9h 56m

New York John F Kennedy Intl

Wed 11/19

6:20 am-12:41 pm

1 stop7h 21m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 12/8

2:10 pm-9:55 pm

1 stop6h 45m

New York LaGuardia

Tue 12/9

9:55 pm-11:20 pm

Nonstop2h 25m

$164

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 12/11

1:45 pm-4:45 pm

Nonstop2h 00m

Hartford Bradley Intl

Sun 12/14

3:35 pm-11:10 pm

1 stop8h 35m

$167

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 12/10

1:14 pm-7:04 pm

1 stop4h 50m

Newark

Wed 12/17

7:05 am-11:55 am

1 stop5h 50m

$177

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 1/17

6:45 am-1:41 pm

1 stop5h 56m

Hartford Bradley Intl

Sun 1/18

5:40 am-8:54 am

1 stop4h 14m

$177

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 11/10

2:50 pm-5:50 pm

Nonstop2h 00m

New York LaGuardia

Tue 11/18

9:55 pm-11:20 pm

Nonstop2h 25m

$183

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Mon 12/8

6:40 pm-11:21 pm

1 stop3h 41m

Newark

Wed 12/10

9:37 am-12:34 pm

1 stop3h 57m

$187

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 12/6

9:29 am-4:30 pm

1 stop6h 01m

Newark

Wed 12/10

7:05 am-11:55 am

1 stop5h 50m

$187

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Mon 12/8

6:40 pm-11:21 pm

1 stop3h 41m

Newark

Tue 12/9

9:37 am-12:34 pm

1 stop3h 57m

$187

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 12/3

1:14 pm-7:04 pm

1 stop4h 50m

Newark

Thu 12/11

7:05 am-11:55 am

1 stop5h 50m

$187

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 60 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 $125). Flying from Chicago Midway Airport to Connecticut in August is currently the most expensive (average of $413). 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 October 29, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 33% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the evening.

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

Use this chart to determine the cheapest time to fly round-trip from Midway to Connecticut. Price data was last updated on October 26, 2025.

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

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 October 29, 2025.
Read reviews from past customers who have flown Southwest 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
4,241 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

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

    Airlines like Frontier, Southwest, and Delta fly from Chicago Midway Airport to Connecticut in about 4h 50m. The time it takes to get you to your destination can typically vary by up to 5h 06m. Chicago Midway Airport and Connecticut are separated by a distance of 708 mi. This flight may include one or multiple stops.

  • 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 $61 on Frontier. Other airlines that offer cheap prices include Southwest from $69 and Delta from $89 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 - Newark, Chicago Midway - New York John F Kennedy Intl 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 $344, our data shows the cheapest flight currently is $113. When looking at the most popular route, (Chicago Midway - New York John F Kennedy Intl), you can expect to pay $110 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 $125). Flying from Chicago Midway Airport to Connecticut in August is currently the most expensive (average of $413). 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.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Sky Harbor Intl flights
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Midway to LaGuardia flights
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Midway to Baltimore flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Charlotte flights
O'Hare Intl to West Palm Beach flights
Midway to Dulles Intl flights
O'Hare Intl to Kahului flights

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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$330FlexibilityNo cancel feeOn-time63%

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