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$67+ 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 11/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$119
(Southwest)

One-way from

$67
(Southwest)

Popular in

December

Cheapest in

August

Average price

$323

Good round-trip deal

$294 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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Highest demand for flights based on searches. 8% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/182:45 pmMDW - LGA
Nonstop2h 00mSouthwest
Wed 11/194:45 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/11$119
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:25 amMDW - LGA
Nonstop2h 05mSouthwest
Sat 11/82:15 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/10$128
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/305:40 pmMDW - LGA
1 stop4h 20mSouthwest
Wed 10/13:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 9/11$129
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/710:55 amMDW - LGA
Nonstop2h 00mSouthwest
Tue 10/146:05 amLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/10$132
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/58:25 amMDW - LGA
Nonstop2h 05mSouthwest
Mon 11/109:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/9$133
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/228:25 amMDW - LGA
Nonstop2h 05mSouthwest
Sat 10/256:45 amLGA - MDW
1 stop7h 15mSouthwest
Deal found 9/11$136
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/17:05 pmMDW - LGA
Nonstop2h 10mSouthwest
Thu 10/26:25 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 9/11$137
This Southwest deal was found by Cheapflights users on 9/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/155:40 pmMDW - LGA
Nonstop2h 05mSouthwest
Mon 11/179:55 pmLGA - MDW
Nonstop2h 25mSouthwest
Deal found 9/11$140
This Gotogate deal was found by Cheapflights users on 9/11. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/302:32 pmMDW - JFK
1 stop9h 36mFrontier
Wed 10/19:00 amJFK - MDW
1 stop7h 58mFrontier
Deal found 9/11$145
This Gotogate deal was found by Cheapflights users on 9/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/301:37 pmMDW - JFK
1 stop9h 56mFrontier
Mon 11/310:00 amJFK - MDW
1 stop9h 39mFrontier
Deal found 9/10$147
This Booking.com deal was found by Cheapflights users on 9/10. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/24:56 pmMDW - JFK
1 stop7h 12mFrontier
Sat 10/41:01 pmJFK - MDW
1 stop11h 40mFrontier
Deal found 9/10$148
This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/81:37 pmMDW - JFK
1 stop9h 56mFrontier
Sun 11/94:00 pmJFK - MDW
1 stop9h 30mFrontier
Deal found 9/11$155

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 September 11, 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 11/5

8:25 am-11:30 am

Nonstop2h 05m

New York LaGuardia

Sat 11/8

2:15 pm-3:45 pm

Nonstop2h 30m

$128

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/9

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Thu 12/11

6:00 am-7:30 am

Nonstop2h 30m

$138

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 11/18

11:15 am-5:05 pm

1 stop4h 50m

New York LaGuardia

Wed 11/19

6:15 am-11:25 am

1 stop6h 10m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 11/5

7:15 pm-10:20 pm

Nonstop2h 05m

New York LaGuardia

Sun 11/9

7:15 am-8:45 am

Nonstop2h 30m

$139

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/22

3:00 pm-9:55 pm

1 stop5h 55m

New York LaGuardia

Sat 10/25

6:45 am-1:00 pm

1 stop7h 15m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/1

8:35 am-2:55 pm

1 stop5h 20m

New York LaGuardia

Sat 10/4

10:40 am-4:30 pm

1 stop6h 50m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 10/21

2:25 pm-5:25 pm

Nonstop2h 00m

New York LaGuardia

Sat 10/25

6:45 am-1:00 pm

1 stop7h 15m

$149

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 11/16

6:10 am-9:15 am

Nonstop2h 05m

New York LaGuardia

Mon 11/17

9:55 pm-11:20 pm

Nonstop2h 25m

$153

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 10/8

5:55 pm-11:10 pm

1 stop4h 15m

New York LaGuardia

Wed 10/15

6:05 am-7:30 am

Nonstop2h 25m

$159

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Fri 10/17

5:28 pm-10:24 am

1 stop15h 56m

New York John F Kennedy Intl

Sun 10/19

6:00 am-9:33 am

1 stop28h 33m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 $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 September 11, 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 September 11, 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
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

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 Southwest, Frontier, and Delta fly from Chicago Midway Airport to Connecticut in about 2h 05m. The time it takes to get you to your destination can typically vary by up to 13h 51m. Chicago Midway Airport and Connecticut are separated by a distance of 722 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 $74 on Southwest. Other airlines that offer cheap prices include Frontier from $78 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 John F Kennedy Intl or Chicago Midway - Newark, Chicago Midway - New York LaGuardia 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 $247, our data shows the cheapest flight currently is $108. When looking at the most popular route, (Chicago Midway - New York LaGuardia), you can expect to pay $119 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.
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Denver flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Orlando flights
O'Hare Intl to Seattle flights
O'Hare Intl to Boston flights
Midway to Las Vegas flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Atlanta flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Miami flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Dulles Intl flights
Midway to LaGuardia flights
O'Hare Intl to Ontario flights
O'Hare Intl to Reagan-National flights
Midway to Atlanta flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to San Diego flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Santa Ana flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Tampa flights
O'Hare Intl to Austin flights
O'Hare Intl to Nashville flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Charlotte flights
O'Hare Intl to Hobby flights
O'Hare Intl to Raleigh flights
O'Hare Intl to Charleston flights
Midway to Orlando flights
O'Hare Intl to George Bush Intcntl flights
O'Hare Intl to Love Field flights
Midway to Hobby flights
Midway to Denver flights
O'Hare Intl to Portland flights
Midway to Miami flights
Midway to Dulles Intl flights
O'Hare Intl to Minneapolis flights
O'Hare Intl to Detroit flights
O'Hare Intl to Burbank 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$342FlexibilityNo cancel feeOn-time63%

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