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$63+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Dec 23 — Dec 301
Mon 12/23
Mon 12/30
1 adult, Economy
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Cheap flight deals from Midway to Connecticut

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Connecticut (USCT). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 18, 2024.

Round-trip from

$108
(Mytrip)

One-way from

$63
(Trip.com)
From Chicago Midway to Connecticut
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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 December 18, 2024.

This CheapOair deal was found by Cheapflights users on 12/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/244:08 pmMDW - JFK
1 stop15h 55mFrontier
Wed 1/2911:00 amJFK - MDW
1 stop9h 06mFrontier
Deal found 12/17$214
This Southwest deal was found by Cheapflights users on 12/16. 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 12/245:00 pmMDW - LGA
1 stop5h 05mSouthwest
Tue 12/316:30 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 12/16$242
This FlightHub deal was found by Cheapflights users on 12/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/238:25 amMDW - BDL
1 stop7h 40mFrontier
Wed 1/14:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 12/18$268
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Tue 12/312:20 pmMDW - LGA
2 stops49h 40mMultiple Airlines
Sun 1/56:54 pmLGA - MDW
2 stops29h 20mMultiple Airlines
Deal found 12/18$309
This Delta deal was found by Cheapflights users on 12/17. 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 12/235:04 pmMDW - EWR
1 stop5h 37mDelta
Wed 1/1512:43 pmEWR - MDW
1 stop6h 04mDelta
Deal found 12/17$311
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Tue 12/312:20 pmMDW - EWR
2 stops16h 39mMultiple Airlines
Sun 1/510:00 pmEWR - MDW
2 stops16h 24mMultiple Airlines
Deal found 12/18$323
This Southwest deal was found by Cheapflights users on 12/17. 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 12/317:20 amMDW - BDL
1 stop7h 15mSouthwest
Wed 1/16:15 pmBDL - MDW
Nonstop2h 35mSouthwest
Deal found 12/17$343
This Delta deal was found by Cheapflights users on 12/17. 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 12/244:50 pmMDW - BDL
1 stop6h 21mDelta
Wed 12/255:20 amBDL - MDW
1 stop4h 30mDelta
Deal found 12/17$352
This Frontier deal was found by Cheapflights users on 12/17. 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 12/198:00 amMDW - LGA
1 stop13h 00mFrontier
Thu 1/910:59 amLGA - MDW
1 stop8h 38mFrontier
Deal found 12/17$358
This Southwest deal was found by Cheapflights users on 12/17. 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 12/256:15 pmMDW - PVD
Nonstop2h 05mSouthwest
Sun 1/58:15 pmPVD - MDW
Nonstop2h 35mSouthwest
Deal found 12/17$369
This Delta deal was found by Cheapflights users on 12/17. 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.
Fri 12/206:25 pmMDW - JFK
1 stop3h 56mDelta
Sat 1/46:29 amJFK - MDW
1 stop5h 39mDelta
Deal found 12/17$385
This Delta deal was found by Cheapflights users on 12/17. 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 12/309:30 amMDW - PVD
1 stop5h 57mDelta
Wed 1/15:35 amPVD - MDW
1 stop4h 15mDelta
Deal found 12/17$466

Find flights from Midway to Connecticut within your budget

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 December 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 2/18

8:30 am-10:00 pm

1 stop12h 30m

New York LaGuardia

Sat 2/22

10:00 pm-11:28 am

1 stop14h 28m

$108

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Sat 2/15

4:19 pm-10:15 am

1 stop16h 56m

New York John F Kennedy Intl

Sat 2/22

11:01 am-10:04 pm

1 stop12h 03m

$110

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/7

5:24 pm-9:00 am

1 stop14h 36m

Newark

Wed 1/8

5:35 pm-10:18 pm

2 stops29h 43m

$144

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 1/25

3:41 pm-9:59 pm

1 stop5h 18m

Newark

Tue 1/28

1:00 pm-6:14 pm

1 stop6h 14m

$146

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/16

6:00 am-9:10 am

Nonstop2h 10m

New York LaGuardia

Thu 1/23

6:30 am-8:00 am

Nonstop2h 30m

$148

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/2

7:17 am-8:00 am

2 stops23h 43m

New York LaGuardia

Mon 1/6

10:59 pm-12:13 am

1 stop26h 14m

$245

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 1/8

6:28 pm-11:14 pm

1 stop3h 46m

New York John F Kennedy Intl

Sat 1/11

6:00 am-10:12 am

1 stop5h 12m

$296

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Sat 1/18

6:35 am-2:45 pm

1 stop7h 10m

Providence-TFGreen

Sun 2/2

7:35 am-9:15 am

Nonstop2h 40m

$297

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 1/16

1:20 pm-4:20 pm

Nonstop2h 00m

Hartford Bradley Intl

Thu 1/23

6:00 am-7:45 am

Nonstop2h 45m

$298

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 1/15

6:00 am-12:32 pm

1 stop5h 32m

Providence-TFGreen

Tue 1/21

7:00 am-1:08 pm

1 stop7h 08m

$306

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 31 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.

Travel insights for flights from Midway to Connecticut

Get recent, data-driven insights about flights from Midway to Connecticut including ideal travel times, pricing trends, and more.

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 December 18, 2024.

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 December 18, 2024.
To help decide which airline to fly from Chicago to Connecticut, see what other customers have to say about Delta, Frontier and Southwest. 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
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Allegiant Air
7.4
Good
829 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.1
Okay
3,479 reviews
Southwest
8.1
Very good
4,848 reviews

Food

7.2

Crew

8.7

Overall

8.1

Boarding

8.2

Comfort

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $63 on Frontier. Other airlines that offer cheap prices include Southwest from $74 and Delta from $83 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 $428, our data shows the cheapest flight currently is $197. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $136 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 December 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$191Average$373FlexibilityNo cancel feeOn-time63%
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