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$58+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Mar 1 — Mar 81
Sun 3/1
Sun 3/8
1 adult, Economy
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Cheap 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 January 30, 2026.

This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:30 am
MDW
-
EWR
Nonstop2h 00m
Frontier
Sun 3/1511:30 am
EWR
-
MDW
Nonstop2h 32m
Frontier
Deal found 1/28$102
This Flightnetwork deal was found by Cheapflights users on 1/29. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/197:30 am
MDW
-
EWR
Nonstop2h 00m
Frontier
Tue 3/2411:30 am
EWR
-
MDW
Nonstop2h 32m
Frontier
Deal found 1/29$103
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Mon 5/1111:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/26$104
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 4/247:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Tue 4/2811:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/28$105
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/237:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/28$107
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/212:20 pm
MDW
-
EWR
1 stop9h 56m
Frontier
Sat 5/911:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/26$108
This Frontier deal was found by Cheapflights users on 1/27. 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.
Thu 4/237:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Sun 4/2611:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/27$111
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/197:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Tue 5/1211:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/26$112
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
-
EWR
1 stop8h 45m
Multiple Airlines
Sun 3/811:30 am
EWR
-
MDW
Nonstop2h 32m
Multiple Airlines
Deal found 1/27$116
This Frontier deal was found by Cheapflights users on 1/28. 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.
Thu 3/127:30 am
MDW
-
EWR
Nonstop2h 00m
Frontier
Sun 3/2211:30 am
EWR
-
MDW
Nonstop2h 32m
Frontier
Deal found 1/28$117
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/162:20 pm
MDW
-
EWR
1 stop6h 09m
Frontier
Mon 4/2011:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/29$118
This Frontier deal was found by Cheapflights users on 1/28. 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.
Fri 4/247:30 am
MDW
-
EWR
Nonstop2h 08m
Frontier
Sat 4/2511:30 am
EWR
-
MDW
Nonstop2h 30m
Frontier
Deal found 1/28$119

Find flight deals from Midway to Connecticut

Keep the following information in mind while searching for Midway to Connecticut flight deals. Data was last updated January 30, 2026.

Round-trip from

$102
(Expedia)

One-way from

$58
(Kiwi.com)

Popular in

November

Cheapest in

August

Average price

$327

Good one-way deal

$206 or less
From Chicago Midway to Connecticut
Search Deals
One-way flight from Chicago Midway to Connecticut
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($13 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals
Price to beat on a one-way flight from Chicago Midway to Connecticut.
Search Deals

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 January 30, 2026.
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 2/25

5:55 pm-9:00 pm

Nonstop2h 05m

New York LaGuardia

Thu 2/26

6:15 am-7:50 am

Nonstop2h 35m

$137

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 3/2

6:05 pm-9:10 pm

Nonstop2h 05m

New York LaGuardia

Mon 3/23

9:55 pm-11:20 pm

Nonstop2h 25m

$147

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sun 3/8

6:00 am-9:05 am

Nonstop2h 05m

New York LaGuardia

Wed 3/11

9:00 am-10:35 am

Nonstop2h 35m

$147

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 2/19

12:22 pm-1:03 am

1 stop11h 41m

New York John F Kennedy Intl

Mon 2/23

1:00 pm-7:47 pm

1 stop7h 47m

$148

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 3/23

8:20 pm-11:20 pm

Nonstop2h 00m

New York LaGuardia

Tue 3/24

9:00 am-10:35 am

Nonstop2h 35m

$157

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 2/19

6:05 am-9:10 am

Nonstop2h 05m

New York LaGuardia

Sun 2/22

6:15 am-7:50 am

Nonstop2h 35m

$163

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 2/28

6:35 am-9:45 am

Nonstop2h 10m

New York LaGuardia

Mon 3/2

6:00 am-7:40 am

Nonstop2h 40m

$163

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 2/2

8:25 am-11:35 am

Nonstop2h 10m

New York LaGuardia

Tue 2/17

6:30 pm-8:15 pm

Nonstop2h 45m

$168

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 2/28

11:45 am-7:00 pm

1 stop6h 15m

Newark

Mon 3/2

5:59 pm-10:31 pm

1 stop5h 32m

$177

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 2/26

6:40 pm-12:53 am

1 stop5h 13m

Newark

Sat 2/28

6:00 am-11:03 am

1 stop6h 03m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

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 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 January 30, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 40% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the morning.

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 January 24, 2026.

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. Tuesday 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 January 30, 2026.
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
4,267 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 9h 36m. Chicago Midway Airport and Connecticut are separated by a distance of 722 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Chicago Midway Airport to Connecticut?

    While some choose either Chicago Midway - Newark or Chicago Midway - New York LaGuardia, 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 $348, our data shows the cheapest flight currently is $107. When looking at the most popular route, (Chicago Midway - New York John F Kennedy Intl), you can expect to pay $138 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.

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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Midway to Tampa flights
O'Hare Intl to Key West flights
Midway to Newark flights
Midway to Atlanta 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 January 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$197Average$325FlexibilityNo cancel feeOn-time63%

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