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$69+ 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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$137
(Southwest)

One-way from

$69
(Southwest)

Good round-trip deal

$329 or less

Good one-way deal

$196 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 March 28, 2025.

This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/246:15 pmMDW - LGA
Nonstop2h 10mSouthwest
Tue 5/276:10 amLGA - MDW
Nonstop2h 20mSouthwest
Deal found 3/26$137
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/166:04 amMDW - EWR
1 stop5h 04mDelta
Sun 4/205:55 amEWR - MDW
1 stop3h 45mDelta
Deal found 3/26$177
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/244:41 pmMDW - LGA
1 stop5h 28mFrontier
Thu 5/16:30 amLGA - MDW
1 stop8h 04mFrontier
Deal found 3/27$198
This Frontier deal was found by Cheapflights users on 3/27. 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.
Wed 4/304:28 pmMDW - JFK
1 stop7h 05mFrontier
Thu 5/811:00 amJFK - MDW
1 stop12h 40mFrontier
Deal found 3/27$198
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/131:08 pmMDW - JFK
1 stop9h 06mDelta
Wed 5/2112:57 pmJFK - MDW
1 stop20h 43mDelta
Deal found 3/26$218
This Frontier deal was found by Cheapflights users on 3/27. 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 5/88:30 amMDW - EWR
1 stop11h 31mFrontier
Mon 5/1910:00 pmEWR - MDW
1 stop12h 20mFrontier
Deal found 3/27$228
This Southwest deal was found by Cheapflights users on 3/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:35 pmMDW - PVD
Nonstop2h 10mSouthwest
Tue 5/65:35 amPVD - MDW
Nonstop2h 30mSouthwest
Deal found 3/26$237
This Frontier deal was found by Cheapflights users on 3/27. 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 4/108:00 amMDW - BDL
1 stop10h 27mFrontier
Mon 4/143:15 pmBDL - MDW
1 stop9h 35mFrontier
Deal found 3/27$248
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/305:59 pmMDW - PVD
1 stop4h 14mDelta
Mon 5/55:50 amPVD - MDW
1 stop3h 50mDelta
Deal found 3/26$257
This Mytrip deal was found by Cheapflights users on 3/27. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/238:04 pmMDW - EWR
1 stop14h 01mAllegiant Air
Fri 5/309:55 amEWR - MDW
1 stop9h 15mAllegiant Air
Deal found 3/27$272
This Southwest deal was found by Cheapflights users on 3/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/68:10 pmMDW - BDL
Nonstop2h 05mSouthwest
Tue 5/135:55 amBDL - MDW
Nonstop2h 25mSouthwest
Deal found 3/27$319
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/54:59 pmMDW - BDL
1 stop6h 00mDelta
Wed 5/145:35 amBDL - MDW
1 stop4h 05mDelta
Deal found 3/27$339

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 March 28, 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

Sat 5/24

6:15 pm-9:25 pm

Nonstop2h 10m

New York LaGuardia

Tue 5/27

6:10 am-7:30 am

Nonstop2h 20m

$137

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 4/16

6:04 am-12:08 pm

1 stop5h 04m

Newark

Sun 4/20

5:55 am-8:40 am

1 stop3h 45m

$177

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 4/24

4:41 pm-11:09 pm

1 stop5h 28m

New York LaGuardia

Thu 5/1

6:30 am-1:34 pm

1 stop8h 04m

$198

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 4/30

4:28 pm-12:33 am

1 stop7h 05m

New York John F Kennedy Intl

Thu 5/8

11:00 am-10:40 pm

1 stop12h 40m

$198

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 5/13

1:08 pm-11:14 pm

1 stop9h 06m

New York John F Kennedy Intl

Wed 5/21

12:57 pm-8:40 am

1 stop20h 43m

$218

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Thu 5/8

8:30 am-9:01 pm

1 stop11h 31m

Newark

Mon 5/19

10:00 pm-9:20 am

1 stop12h 20m

$228

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 4/30

6:35 pm-9:45 pm

Nonstop2h 10m

Providence-TFGreen

Tue 5/6

5:35 am-7:05 am

Nonstop2h 30m

$237

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 4/10

8:00 am-7:27 pm

1 stop10h 27m

Hartford Bradley Intl

Mon 4/14

3:15 pm-11:50 pm

1 stop9h 35m

$248

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 4/30

5:59 pm-11:13 pm

1 stop4h 14m

Providence-TFGreen

Mon 5/5

5:50 am-8:40 am

1 stop3h 50m

$257

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Sun 6/1

12:55 pm-8:22 am

1 stop20h 27m

$261

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 34 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 March 28, 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 March 28, 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
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,271 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $69 on Southwest. Other airlines that offer cheap prices include Frontier from $98 and Delta from $99 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 $295, our data shows the cheapest flight currently is $88. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $179 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.
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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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$197Average$334FlexibilityNo cancel feeOn-time63%
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