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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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
May 6 — May 131
Tue 5/6
Tue 5/13
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 May 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
2 stars

Round-trip from

$137
(Southwest)

One-way from

$89
(Southwest)

Good round-trip deal

$319 or less

Good one-way deal

$141 or less
Provider with most accurate pricing for Chicago (CHI)-Springfield (SFY) flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Springfield (SFY) flights.
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From Chicago Midway to Connecticut
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One-way flight from Chicago Midway to Connecticut
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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 May 1, 2025.

This Southwest deal was found by Cheapflights users on 4/30. 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 5/145:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Wed 5/219:45 pmLGA - MDW
Nonstop2h 15mSouthwest
Deal found 4/30$137
This Delta deal was found by Cheapflights users on 4/30. 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.
Sat 6/215:53 pmMDW - EWR
1 stop4h 07mDelta
Tue 6/247:05 amEWR - MDW
1 stop5h 54mDelta
Deal found 4/30$179
This Cheapflightsfares deal was found by Cheapflights users on 4/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/69:34 amMDW - LGA
1 stop5h 55mFrontier
Wed 5/76:30 amLGA - MDW
1 stop5h 56mFrontier
Deal found 4/30$195
This Lucky2Go deal was found by Cheapflights users on 4/30. 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 Lucky2Go is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mMultiple Airlines
Fri 6/611:04 amEWR - MDW
1 stop22h 43mMultiple Airlines
Deal found 4/30$196
This Frontier deal was found by Cheapflights users on 4/30. 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 5/142:12 pmMDW - JFK
1 stop9h 23mFrontier
Wed 5/216:00 amJFK - MDW
1 stop6h 26mFrontier
Deal found 4/30$198
This Mytrip deal was found by Cheapflights users on 4/30. 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.
Fri 5/308:04 pmMDW - EWR
1 stop14h 01mAllegiant Air
Fri 6/69:55 amEWR - MDW
1 stop5h 08mAllegiant Air
Deal found 4/30$202
This eDestinos deal was found by Cheapflights users on 4/30. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/146:20 amMDW - EWR
1 stop17h 24mFrontier
Sat 6/215:59 amEWR - MDW
1 stop17h 29mFrontier
Deal found 4/30$213
This Southwest deal was found by Cheapflights users on 4/30. 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 5/216:35 pmMDW - PVD
Nonstop2h 10mSouthwest
Sat 5/245:25 amPVD - MDW
Nonstop2h 30mSouthwest
Deal found 4/30$288
This Delta deal was found by Cheapflights users on 4/30. 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.
Wed 5/1412:48 pmMDW - JFK
1 stop8h 11mDelta
Tue 5/207:15 amJFK - MDW
1 stop6h 13mDelta
Deal found 4/30$291
This Delta deal was found by Cheapflights users on 4/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/26:25 pmMDW - PVD
1 stop3h 57mDelta
Thu 6/55:50 amPVD - MDW
1 stop3h 50mDelta
Deal found 4/29$305
This Southwest deal was found by Cheapflights users on 4/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/311:55 pmMDW - BDL
Nonstop2h 05mSouthwest
Mon 6/25:40 pmBDL - MDW
1 stop5h 20mSouthwest
Deal found 4/29$306
This Booking.com deal was found by Cheapflights users on 4/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/410:55 amMDW - BDL
1 stop7h 19mFrontier
Thu 5/88:14 pmBDL - MDW
1 stop17h 10mFrontier
Deal found 4/29$310

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 May 1, 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 5/14

5:50 pm-9:00 pm

Nonstop2h 10m

New York LaGuardia

Wed 5/21

9:45 pm-11:00 pm

Nonstop2h 15m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 6/21

5:53 pm-11:00 pm

1 stop4h 07m

Newark

Tue 6/24

7:05 am-11:59 am

1 stop5h 54m

$179

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 5/6

9:34 am-4:29 pm

1 stop5h 55m

New York LaGuardia

Wed 5/7

6:30 am-11:26 am

1 stop5h 56m

$195

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Fri 6/6

11:04 am-8:47 am

1 stop22h 43m

$196

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 5/14

2:12 pm-12:35 am

1 stop9h 23m

New York John F Kennedy Intl

Wed 5/21

6:00 am-11:26 am

1 stop6h 26m

$198

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Fri 6/6

9:55 am-2:03 pm

1 stop5h 08m

$202

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 6/14

6:20 am-12:44 am

1 stop17h 24m

Newark

Sat 6/21

5:59 am-10:28 pm

1 stop17h 29m

$213

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 5/21

6:35 pm-9:45 pm

Nonstop2h 10m

Providence-TFGreen

Sat 5/24

5:25 am-6:55 am

Nonstop2h 30m

$288

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 5/14

12:48 pm-9:59 pm

1 stop8h 11m

New York John F Kennedy Intl

Tue 5/20

7:15 am-12:28 pm

1 stop6h 13m

$291

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Mon 6/2

6:25 pm-11:22 pm

1 stop3h 57m

Providence-TFGreen

Thu 6/5

5:50 am-8:40 am

1 stop3h 50m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 32 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 June is currently the most expensive (average of $357). 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 May 1, 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.

Rainfall in Connecticut by month

Plan your trip to Connecticut by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Connecticut ranges from 3.1 - 4.1 inches per month. September is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Connecticut when rainfall is around 3.1 in.

Temperature in Connecticut by month

Plan your trip to Connecticut by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Connecticut, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 24.8 F).

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 May 1, 2025.
To help decide which airline to fly from Chicago to Connecticut, see what other customers have to say about Southwest, Delta and Allegiant Air. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,294 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,934 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Allegiant Air
7.3
Good
734 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Frontier
6.0
Okay
3,287 reviews
Southwest
8.0
Very good
4,294 reviews

Overall

8.0

Boarding

8.2

Entertainment

7.6

Comfort

8.0

Food

7.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 $89 on Southwest. Other airlines that offer cheap prices include Delta from $89 and Allegiant Air from $95 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 - 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 $286, our data shows the cheapest flight currently is $136. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $163 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 June is currently the most expensive (average of $357). 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.

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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 LaGuardia flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Newark flights
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O'Hare Intl to Seattle flights
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O'Hare Intl to Miami flights
Midway to Newark flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Boston flights
Midway to Dallas/Fort Worth flights
Midway to Las Vegas flights
O'Hare Intl to Philadelphia flights
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O'Hare Intl to Baltimore flights
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Midway to Atlanta flights
O'Hare Intl to Nashville flights
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O'Hare Intl to Austin flights
Midway to Hobby flights
O'Hare Intl to Santa Ana flights
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Midway to Sky Harbor Intl flights
Midway to LaGuardia flights
O'Hare Intl to Burbank flights
O'Hare Intl to Savannah flights
Midway to Orlando flights
O'Hare Intl to Love Field flights
O'Hare Intl to Raleigh flights
Midway to Denver flights
Midway to San Francisco flights
O'Hare Intl to Minneapolis flights
O'Hare Intl to Fort Myers flights
Midway to Seattle flights

Top 2 airlines flying from Midway to Connecticut

Discover the top 2 airlines 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$197Average$351FlexibilityNo cancel feeOn-time63%

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