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$104+ 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 25 — Sep 11
Tue 8/25
Tue 9/1
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 July 26, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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 9/25:10 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sat 9/53:15 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Deal found 7/23$207
This Southwest deal was found by Cheapflights users on 7/24. 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 8/226:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sun 8/236:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 7/24$217
This Southwest deal was found by Cheapflights users on 7/24. 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 8/267:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Fri 8/286:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 7/24$218
This Southwest deal was found by Cheapflights users on 7/22. 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 8/187:05 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Tue 8/257:25 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/22$227
This Southwest deal was found by Cheapflights users on 7/24. 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 9/87:15 am
MDW
-
LGA
1 stop7h 35m
Southwest
Tue 9/1510:55 am
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/24$228
This Southwest deal was found by Cheapflights users on 7/24. 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 9/95:45 pm
MDW
-
LGA
Nonstop2h 10m
Southwest
Sat 9/125:50 pm
LGA
-
MDW
Nonstop2h 30m
Southwest
Deal found 7/24$229
This Southwest deal was found by Cheapflights users on 7/21. 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.
Sun 8/165:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Thu 9/32:35 pm
LGA
-
MDW
1 stop8h 20m
Southwest
Deal found 7/21$233
This Southwest deal was found by Cheapflights users on 7/22. 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 8/156:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Sat 8/228:20 am
LGA
-
MDW
1 stop6h 45m
Southwest
Deal found 7/22$237
This Delta deal was found by Cheapflights users on 7/25. 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.
Tue 8/186:42 pm
MDW
-
EWR
1 stop3h 43m
Delta
Thu 8/2012:00 pm
EWR
-
MDW
1 stop5h 15m
Delta
Deal found 7/25$237
This Frontier deal was found by Cheapflights users on 7/25. 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 9/811:50 am
MDW
-
EWR
1 stop12h 13m
Frontier
Tue 9/1511:35 am
EWR
-
MDW
1 stop7h 11m
Frontier
Deal found 7/25$239
This Frontier deal was found by Cheapflights users on 7/22. 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 9/411:50 am
MDW
-
EWR
1 stop12h 13m
Frontier
Sat 9/125:55 am
EWR
-
MDW
1 stop6h 03m
Frontier
Deal found 7/22$240
This Priceline deal was found by Cheapflights users on 7/22. 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.
Sat 8/2211:45 am
MDW
-
EWR
1 stop8h 43m
Frontier
Tue 8/255:55 am
EWR
-
MDW
1 stop6h 00m
Frontier
Deal found 7/22$243

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 July 26, 2026.

Round-trip from

$207
(Southwest)

One-way from

$104
(Southwest)

Popular in

April

Cheapest in

September

Average price

$481

Good round-trip deal

$297 or less

Good one-way deal

$202 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. 19% potential increase in price ($98 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Connecticut.
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 July 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Connecticut that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 9/1

5:10 am-8:10 am

Nonstop2h 00m

New York LaGuardia

Wed 9/2

4:10 pm-5:40 pm

Nonstop2h 30m

$207

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/2

7:05 pm-10:10 pm

Nonstop2h 05m

New York LaGuardia

Tue 9/8

7:25 am-8:45 am

Nonstop2h 20m

$207
Quickest round-trip

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 9/2

5:10 am-8:10 am

Nonstop2h 00m

New York LaGuardia

Wed 9/2

9:35 pm-10:50 pm

Nonstop2h 15m

$227

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/11

5:15 pm-8:20 pm

Nonstop2h 05m

New York LaGuardia

Sun 9/13

6:00 am-7:15 am

Nonstop2h 15m

$237

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 8/18

2:40 pm-11:00 pm

1 stop7h 20m

New York LaGuardia

Wed 8/19

6:00 am-7:15 am

Nonstop2h 15m

$237

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/15

9:35 am-12:40 pm

Nonstop2h 05m

New York LaGuardia

Mon 8/17

3:00 pm-7:45 pm

1 stop5h 45m

$237

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 8/20

12:50 pm-3:55 pm

Nonstop2h 05m

New York LaGuardia

Thu 8/27

8:35 am-3:25 pm

1 stop7h 50m

$239

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 8/28

9:50 am-4:55 pm

1 stop6h 05m

New York LaGuardia

Sun 8/30

6:00 am-7:15 am

Nonstop2h 15m

$239

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Fri 9/18

5:30 pm-11:20 pm

1 stop4h 50m

New York LaGuardia

Sat 9/19

7:35 am-8:55 am

Nonstop2h 20m

$239

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 8/21

6:42 pm-11:25 pm

1 stop3h 43m

Newark

Wed 8/26

12:00 pm-4:15 pm

1 stop5h 15m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/21

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 July 26, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 37% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the afternoon.

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 July 18, 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. Thursday at noon 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 July 26, 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
4,233 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,233 reviews
Southwest
8.0
Very good
4,233 reviews

Entertainment

7.5

Food

7.0

Overall

8.0

Comfort

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

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 and Delta fly from Chicago Midway Airport to Connecticut in about 2h. The time it takes to get you to your destination can typically vary by up to 1h 43m. 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 - 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 $327, our data shows the cheapest flight currently is $144. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $240 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 Orlando flights
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Midway to Minneapolis flights
Midway to Dulles Intl flights
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Midway to Denver flights
O'Hare Intl to Portland 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 July 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$248Average$403FlexibilityNo cancel feeOn-time63%

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