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$60+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This CheapOair deal was found by Cheapflights users on 11/20. 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.
Mon 12/236:00 amMDW - JFK
1 stop26h 03mFrontier
Wed 1/811:00 amJFK - MDW
1 stop7h 57mFrontier
Deal found 11/20$134
This CheapOair deal was found by Cheapflights users on 11/19. 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.
Mon 12/169:57 pmMDW - LGA
1 stop17h 32mFrontier
Tue 12/315:29 pmLGA - MDW
1 stop15h 52mFrontier
Deal found 11/19$138
This Southwest deal was found by Cheapflights users on 11/19. 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 12/107:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Thu 12/126:30 amLGA - MDW
Nonstop2h 30mSouthwest
Deal found 11/19$148
This Delta deal was found by Cheapflights users on 11/19. 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 12/102:15 pmMDW - EWR
1 stop8h 28mDelta
Thu 12/126:00 amEWR - MDW
1 stop3h 58mDelta
Deal found 11/19$176
This eDestinos deal was found by Cheapflights users on 11/19. 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 12/1012:57 pmMDW - EWR
1 stop20h 58mMultiple Airlines
Thu 12/1210:14 amEWR - MDW
2 stops26h 27mMultiple Airlines
Deal found 11/19$189
This eDestinos deal was found by Cheapflights users on 11/19. 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 12/1012:57 pmMDW - LGA
1 stop18h 03mMultiple Airlines
Thu 12/126:29 amLGA - MDW
2 stops41h 16mMultiple Airlines
Deal found 11/19$190
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Mon 12/1611:33 amMDW - BDL
1 stop21h 19mFrontier
Wed 12/184:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 11/20$208
This Southwest deal was found by Cheapflights users on 11/19. 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 12/1212:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Mon 12/167:30 amBDL - MDW
Nonstop2h 30mSouthwest
Deal found 11/19$288
This Delta deal was found by Cheapflights users on 11/20. 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 12/145:50 pmMDW - JFK
1 stop4h 31mDelta
Mon 1/137:05 amJFK - MDW
1 stop7h 03mDelta
Deal found 11/20$294
This eDestinos deal was found by Cheapflights users on 11/20. 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.
Mon 12/169:57 pmMDW - PVD
2 stops24h 02mMultiple Airlines
Fri 12/207:12 pmPVD - MDW
2 stops36h 27mMultiple Airlines
Deal found 11/20$311
This Southwest deal was found by Cheapflights users on 11/20. 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 12/196:30 amMDW - PVD
1 stop8h 50mSouthwest
Sun 12/228:15 pmPVD - MDW
Nonstop2h 35mSouthwest
Deal found 11/20$327
This Delta deal was found by Cheapflights users on 11/20. 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 12/165:50 pmMDW - PVD
1 stop4h 54mDelta
Wed 12/185:00 amPVD - MDW
1 stop4h 58mDelta
Deal found 11/20$331

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Thu 1/23

7:25 am-5:00 pm

1 stop8h 35m

New York LaGuardia

Tue 1/28

10:59 am-4:16 pm

1 stop6h 17m

$104

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Thu 1/30

12:43 pm-6:30 am

1 stop16h 47m

New York John F Kennedy Intl

Mon 2/3

11:00 am-3:43 pm

1 stop5h 43m

$108

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 2/12

8:12 am-9:10 pm

1 stop11h 58m

Newark

Tue 2/18

10:10 pm-7:07 am

1 stop9h 57m

$116

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 1/7

6:00 am-9:10 am

Nonstop2h 10m

New York LaGuardia

Mon 1/13

6:30 am-8:00 am

Nonstop2h 30m

$148

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Tue 1/7

9:34 am-5:00 pm

1 stop6h 26m

Newark

Sat 1/11

1:00 pm-4:12 pm

1 stop4h 12m

$166

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 1/17

12:51 pm-2:00 pm

1 stop24h 09m

Newark

Fri 1/31

10:00 pm-11:29 pm

1 stop26h 29m

$171

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Tue 12/10

12:57 pm-8:00 am

1 stop18h 03m

New York LaGuardia

Thu 12/12

6:29 am-10:45 pm

2 stops41h 16m

$190

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Mon 12/16

11:33 am-9:52 am

1 stop21h 19m

Hartford Bradley Intl

Wed 12/18

4:00 pm-9:17 pm

1 stop6h 17m

$208

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 1/8

12:25 pm-3:25 pm

Nonstop2h 00m

Hartford Bradley Intl

Sun 1/12

6:55 pm-8:30 pm

Nonstop2h 35m

$268

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 1/8

6:00 am-1:14 pm

1 stop6h 14m

Hartford Bradley Intl

Sat 1/11

5:20 am-8:54 am

1 stop4h 34m

$286

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 38 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 November 21, 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 November 21, 2024.
To help decide which airline to fly from Chicago to Connecticut, see what other customers have to say about Frontier, Delta and Porter Airlines. 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
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Porter Airlines
7.8
Good
286 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Air Transat
7.8
Good
389 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,810 reviews
Southwest
8.1
Very good
5,015 reviews

Entertainment

7.7

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $60 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 $318, our data shows the cheapest flight currently is $132. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $132 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, December is the cheapest month in which you can book a flight from Chicago Midway Airport to Connecticut (average of $280). Flying from Chicago Midway Airport to Connecticut in June is currently the most expensive (average of $359). 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$191Average$373FlexibilityNo cancel feeOn-time63%
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