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$89+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 June 9, 2026.

This Southwest deal was found by Cheapflights users on 6/8. 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.
Thu 8/67:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Tue 8/116:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 6/8$177
This Southwest deal was found by Cheapflights users on 6/9. 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.
Thu 8/205:15 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Thu 8/276:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 6/9$178
This Southwest deal was found by Cheapflights users on 6/8. 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 8/119:30 am
MDW
-
LGA
Nonstop2h 05m
Southwest
Sat 8/158:20 am
LGA
-
MDW
1 stop6h 45m
Southwest
Deal found 6/8$179
This Southwest deal was found by Cheapflights users on 6/9. 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.
Tue 8/258:50 am
MDW
-
LGA
2 stops7h 15m
Southwest
Mon 8/316:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 6/9$180
This Southwest deal was found by Cheapflights users on 6/8. 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.
Mon 8/105:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Wed 8/196:05 am
LGA
-
MDW
1 stop6h 55m
Southwest
Deal found 6/8$181
This Southwest deal was found by Cheapflights users on 6/7. 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.
Thu 8/275:00 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Mon 8/318:55 pm
LGA
-
MDW
Nonstop2h 20m
Southwest
Deal found 6/7$182
This Southwest deal was found by Cheapflights users on 6/8. 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 8/188:15 am
MDW
-
LGA
1 stop5h 05m
Southwest
Tue 8/184:40 pm
LGA
-
MDW
1 stop7h 30m
Southwest
Deal found 6/8$183
This Southwest deal was found by Cheapflights users on 6/8. 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 8/47:10 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Sat 8/88:20 am
LGA
-
MDW
1 stop8h 35m
Southwest
Deal found 6/8$184
This Southwest deal was found by Cheapflights users on 6/8. 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.
Fri 9/117:50 pm
MDW
-
LGA
Nonstop2h 05m
Southwest
Mon 9/146:00 am
LGA
-
MDW
Nonstop2h 15m
Southwest
Deal found 6/8$185
This Southwest deal was found by Cheapflights users on 6/7. 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 9/158:20 am
MDW
-
LGA
1 stop6h 45m
Southwest
Tue 9/155:45 pm
LGA
-
MDW
1 stop5h 05m
Southwest
Deal found 6/7$186
This Southwest deal was found by Cheapflights users on 6/7. 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 7/85:15 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Wed 7/157:25 am
LGA
-
MDW
Nonstop2h 25m
Southwest
Deal found 6/7$187
This Southwest deal was found by Cheapflights users on 6/8. 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 9/135:25 am
MDW
-
LGA
Nonstop2h 00m
Southwest
Tue 9/158:50 am
LGA
-
MDW
1 stop7h 35m
Southwest
Deal found 6/8$188

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 June 9, 2026.

Round-trip from

$177
(Southwest)

One-way from

$89
(Southwest)

Popular in

April

Cheapest in

August

Average price

$393

Good round-trip deal

$408 or less

Good one-way deal

$191 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. 21% potential increase in price ($106 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 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.
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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 June 9, 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 7/7

7:45 pm-11:00 pm

Nonstop2h 15m

New York LaGuardia

Sat 7/11

9:10 pm-10:50 pm

Nonstop2h 40m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 8/15

6:00 am-9:00 am

Nonstop2h 00m

New York LaGuardia

Wed 8/19

5:40 pm-7:10 pm

Nonstop2h 30m

$187

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 8/26

8:50 am-5:05 pm

2 stops7h 15m

New York LaGuardia

Fri 8/28

6:00 am-7:15 am

Nonstop2h 15m

$190

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 7/8

9:54 am-5:53 pm

1 stop6h 59m

Newark

Sat 7/11

6:15 am-1:09 pm

1 stop7h 54m

$207

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 8/13

6:42 pm-11:25 pm

1 stop3h 43m

Newark

Tue 8/18

10:30 am-4:15 pm

1 stop6h 45m

$207

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 9/5

4:52 pm-11:56 pm

1 stop6h 04m

Newark

Tue 9/15

6:00 am-9:07 am

1 stop4h 07m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Mon 8/10

7:50 pm-10:55 pm

Nonstop2h 05m

New York LaGuardia

Wed 8/19

10:55 am-12:15 pm

Nonstop2h 20m

$217

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 8/12

7:10 pm-10:15 pm

Nonstop2h 05m

New York LaGuardia

Wed 8/19

6:30 am-11:50 am

1 stop6h 20m

$222

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 7/22

7:45 pm-11:00 pm

Nonstop2h 15m

New York LaGuardia

Wed 7/29

8:55 am-3:55 pm

1 stop8h 00m

$222

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 7/4

12:30 pm-10:55 pm

1 stop9h 25m

New York LaGuardia

Sun 7/5

6:00 am-7:20 am

Nonstop2h 20m

$237

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 60 resultsSorted by cheapest first
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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 June 9, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 50% on flights from Chicago Midway Airport to Connecticut by exploring options for tickets in the afternoon.

How much does it cost to fly round-trip from Chicago Midway Airport to Connecticut?

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 May 30, 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 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 June 9, 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
7.9
Good
4,240 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,240 reviews
Southwest
7.9
Good
4,240 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 15m. The time it takes to get you to your destination can typically vary by up to 4h 44m. 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 John F Kennedy Intl or Chicago Midway - New York LaGuardia, 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 $325, our data shows the cheapest flight currently is $166. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $180 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 Dallas/Fort Worth flights
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Midway to Los Angeles flights
Midway to Atlanta flights
O'Hare Intl to Nashville flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
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Midway to Orlando flights
Midway to Miami flights
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Midway to Denver flights
O'Hare Intl to Austin flights
Midway to Tampa flights
Midway to Baltimore flights
O'Hare Intl to Kansas City flights
O'Hare Intl to Minneapolis flights
Midway to Hobby flights
O'Hare Intl to Raleigh 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 June 9, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$240Average$350FlexibilityNo cancel feeOn-time63%

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