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Midway

$59+ Cheap flights from Connecticut to Midway (MDW)

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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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Cheap flight deals from Connecticut to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Connecticut (USCT) to Midway (MDW). 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 Connecticut to Midway

Cheapest flights from Connecticut to Midway
Explore the most affordable flight options available from Connecticut to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 21, 2024.

This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/511:19 amJFK - MDW
1 stop25h 22mFrontier
Mon 12/95:01 amMDW - JFK
1 stop28h 15mFrontier
Deal found 11/20$115
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.
Thu 12/1210:59 pmLGA - MDW
1 stop26h 14mFrontier
Mon 12/169:57 pmMDW - LGA
1 stop17h 32mFrontier
Deal found 11/20$138
This Southwest deal was found by Cheapflights users on 11/21. 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 12/76:30 amLGA - MDW
Nonstop2h 30mSouthwest
Wed 12/117:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 11/21$148
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.
Thu 12/126:00 amEWR - MDW
1 stop3h 58mDelta
Tue 1/76:00 amMDW - EWR
1 stop5h 10mDelta
Deal found 11/20$171
This Frontier deal was found by Cheapflights users on 11/21. 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 12/1210:55 amBDL - MDW
1 stop27h 59mFrontier
Sun 12/155:15 amMDW - BDL
1 stop26h 42mFrontier
Deal found 11/21$240
This Southwest deal was found by Cheapflights users on 11/21. 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 12/167:30 amBDL - MDW
Nonstop2h 30mSouthwest
Mon 12/1612:25 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 11/21$273
This Delta deal was found by Cheapflights users on 11/21. 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 12/175:25 amBDL - MDW
1 stop4h 33mDelta
Tue 12/244:50 pmMDW - BDL
1 stop6h 21mDelta
Deal found 11/21$276
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 12/73:59 pmJFK - MDW
1 stop7h 07mDelta
Sat 12/145:50 pmMDW - JFK
1 stop4h 31mDelta
Deal found 11/20$294
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.
Mon 12/166:50 amPVD - MDW
Nonstop2h 40mSouthwest
Wed 12/1810:05 amMDW - PVD
1 stop5h 25mSouthwest
Deal found 11/20$295
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.
Tue 12/105:00 amPVD - MDW
1 stop4h 58mDelta
Tue 12/179:30 amMDW - PVD
1 stop5h 50mDelta
Deal found 11/20$320
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.
Thu 11/219:12 amEWR - MDW
2 stops15h 03mMultiple Airlines
Thu 11/286:05 amMDW - EWR
1 stop13h 55mMultiple Airlines
Deal found 11/19$334
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1310:00 amEWR - MDW
1 stop7h 40mPorter Airlines
Wed 12/1812:05 pmMDW - EWR
1 stop4h 55mPorter Airlines
Deal found 11/20$510

Find flights from Connecticut to Midway within your budget

Customize your flight search to find flights from Connecticut to Midway 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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 1/18

3:00 pm-10:02 am

1 stop20h 02m

Chicago Midway

Mon 1/20

7:15 am-10:05 am

1 stop25h 50m

$114

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 1/25

5:00 pm-10:02 am

1 stop18h 02m

Chicago Midway

Mon 1/27

6:15 am-3:10 pm

1 stop7h 55m

$114

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Fri 1/10

9:35 pm-11:05 pm

Nonstop2h 30m

Chicago Midway

Mon 1/13

8:05 pm-11:10 pm

Nonstop2h 05m

$148

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 1/11

1:00 pm-4:12 pm

1 stop4h 12m

Chicago Midway

Wed 1/15

10:19 am-5:37 pm

1 stop6h 18m

$166

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/12

10:55 am-1:54 pm

1 stop27h 59m

Chicago Midway

Sun 12/15

5:15 am-8:57 am

1 stop26h 42m

$240

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 12/16

7:30 am-9:00 am

Nonstop2h 30m

Chicago Midway

Mon 12/16

12:25 pm-3:25 pm

Nonstop2h 00m

$273

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/17

5:25 am-8:58 am

1 stop4h 33m

Chicago Midway

Tue 12/24

4:50 pm-12:11 am

1 stop6h 21m

$276

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Fri 1/24

5:55 am-7:40 am

Nonstop2h 45m

Chicago Midway

Mon 1/27

6:05 pm-9:15 pm

Nonstop2h 10m

$286

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Thu 2/13

12:59 pm-6:14 pm

1 stop6h 15m

Chicago Midway

Mon 2/17

2:08 pm-7:59 pm

1 stop4h 51m

$294

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Mon 1/13

7:00 am-1:08 pm

1 stop7h 08m

Chicago Midway

Thu 1/16

6:00 am-12:32 pm

1 stop5h 32m

$304

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 Connecticut to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Connecticut 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 Connecticut to Midway

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

What is the cheapest month to book a flight from Connecticut to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $160). Flying from Connecticut to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 CT to MDW?

Find hourly flight availability from Connecticut to Midway. 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.

When flying from Connecticut to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Midway by month

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

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

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

If weather is an important factor for your trip to Chicago Midway Airport, 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 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated November 21, 2024.
To help decide which airline to fly from Connecticut to Chicago, see what other customers have to say about Frontier, Southwest and Delta. 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
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

Porter Airlines
7.8
Good
288 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

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
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Overall

8.1

Reviews

1 / 10

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

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Food

7.2

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

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 Connecticut to Midway. 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 Connecticut to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $61 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 Connecticut to Chicago Midway Airport?

    The most popular flight routes from Connecticut to Chicago Midway Airport are Newark - Chicago Midway, New York John F Kennedy Intl - Chicago Midway and New York LaGuardia - Chicago Midway.

  • What are the cheapest flights from Connecticut to Chicago Midway Airport?

    The cheapest flight price from Connecticut to Chicago Midway Airport is $173. On average you can expect to pay $364. The most popular route, (Newark - Chicago Midway), can usually be booked for $136.

  • Can I find deals for flights from Connecticut to Midway that include hotel bookings?

    Yes. In addition to deals on Connecticut to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Midway.

  • Can I find deals for business class flights from Connecticut to Midway?

    Yes. Cheapflights offers flight deals from Connecticut to Midway 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 Connecticut to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Connecticut to Chicago Midway Airport (average of $160). Flying from Connecticut to Chicago Midway Airport in October is currently the most expensive (average of $232). 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 Connecticut to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
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LaGuardia to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
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San Francisco to O'Hare Intl flights
Newark to Midway flights
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Dallas/Fort Worth to Midway flights
Atlanta to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Baltimore to O'Hare Intl flights
Atlanta to Midway flights
Dulles Intl to O'Hare Intl flights
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Sky Harbor Intl to O'Hare Intl flights
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Fort Lauderdale to O'Hare Intl flights
Los Angeles to Midway flights
Minneapolis to O'Hare Intl flights
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Baltimore to Midway flights
Hobby to Midway flights
Burbank to O'Hare Intl flights
LaGuardia to Midway flights
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San Francisco to Midway flights
Seattle to Midway flights
Portland to O'Hare Intl flights
Minneapolis to Midway flights
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Dulles Intl to Midway flights
Raleigh to O'Hare Intl flights
San Jose to O'Hare Intl flights
Charlotte to O'Hare Intl flights
Austin to O'Hare Intl flights
Love Field to O'Hare Intl flights
Reagan-National to Midway flights
Nashville to O'Hare Intl flights
Oakland to O'Hare Intl flights
Boston to Midway flights
Denver to Midway flights

Top 4 airlines flying from Connecticut to Midway

Discover the top 4 airlines that operate flights from Connecticut to Midway. 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$253FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$364FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$190Average$347FlexibilityNo cancel feeOn-time63%
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