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$55+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
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 January 21, 2025.

Round-trip from

$112
(Trip.com)

One-way from

$59
(Mytrip)

Good round-trip deal

$415 or less

Good one-way deal

$208 or less
From Connecticut to Chicago Midway
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One-way flight from Connecticut to Chicago Midway
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Price to beat on a round-trip flight from Connecticut to Chicago Midway.
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Price to beat on a one-way flight from Connecticut to Chicago Midway.
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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 January 21, 2025.

This Frontier deal was found by Cheapflights users on 1/21. 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.
Sat 4/191:00 pmJFK - MDW
1 stop9h 52mFrontier
Mon 4/216:44 pmMDW - JFK
1 stop11h 43mFrontier
Deal found 1/21$114
This Trip.com deal was found by Cheapflights users on 1/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1210:00 pmLGA - MDW
1 stop14h 28mFrontier
Tue 2/188:30 amMDW - LGA
1 stop24h 30mFrontier
Deal found 1/20$114
This Southwest deal was found by Cheapflights users on 1/20. 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.
Wed 2/129:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Wed 2/196:00 amMDW - LGA
Nonstop2h 10mSouthwest
Deal found 1/20$147
This eDestinos deal was found by Cheapflights users on 1/21. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/2010:20 pmEWR - MDW
1 stop26h 38mFrontier
Thu 2/274:13 pmMDW - EWR
1 stop27h 57mFrontier
Deal found 1/21$150
This Delta deal was found by Cheapflights users on 1/21. 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.
Sat 2/226:00 amEWR - MDW
1 stop5h 16mDelta
Wed 3/1212:51 pmMDW - EWR
1 stop6h 39mDelta
Deal found 1/21$159
This Delta deal was found by Cheapflights users on 1/20. 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 2/46:00 amPVD - MDW
1 stop6h 59mDelta
Mon 2/106:00 amMDW - PVD
1 stop5h 32mDelta
Deal found 1/20$217
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/95:25 pmPVD - MDW
1 stop15h 25mMultiple Airlines
Tue 3/116:36 pmMDW - PVD
1 stop13h 41mMultiple Airlines
Deal found 1/21$253
This Delta deal was found by Cheapflights users on 1/21. 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 2/116:10 amBDL - MDW
1 stop6h 49mDelta
Tue 2/185:05 pmMDW - BDL
1 stop6h 04mDelta
Deal found 1/21$277
This Frontier deal was found by Cheapflights users on 1/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/72:59 pmBDL - MDW
1 stop9h 59mFrontier
Mon 3/246:20 amMDW - BDL
1 stop6h 39mFrontier
Deal found 1/20$280
This Southwest deal was found by Cheapflights users on 1/21. 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.
Wed 2/265:55 amPVD - MDW
Nonstop2h 45mSouthwest
Thu 2/278:20 pmMDW - PVD
Nonstop2h 10mSouthwest
Deal found 1/21$285
This Southwest deal was found by Cheapflights users on 1/21. 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.
Wed 4/26:00 amBDL - MDW
Nonstop2h 30mSouthwest
Fri 4/44:45 pmMDW - BDL
1 stop4h 10mSouthwest
Deal found 1/21$287
This Delta deal was found by Cheapflights users on 1/20. 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 2/1312:59 pmJFK - MDW
1 stop6h 12mDelta
Wed 2/1912:44 pmMDW - JFK
1 stop10h 58mDelta
Deal found 1/20$289

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 2,558,603 searches. Data last updated January 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Thu 2/6

10:59 am-6:26 pm

1 stop8h 27m

Chicago Midway

Wed 2/12

6:00 am-8:59 pm

1 stop13h 59m

$112

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 4/19

1:00 pm-9:52 pm

1 stop9h 52m

Chicago Midway

Tue 4/22

3:20 pm-12:33 am

1 stop8h 13m

$114

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 2/12

9:35 pm-11:05 pm

Nonstop2h 30m

Chicago Midway

Wed 2/19

6:00 am-9:10 am

Nonstop2h 10m

$147

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 2/20

10:20 pm-11:58 pm

1 stop26h 38m

Chicago Midway

Thu 2/27

4:13 pm-9:10 pm

1 stop27h 57m

$150

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 2/22

6:00 am-10:16 am

1 stop5h 16m

Chicago Midway

Tue 3/11

6:42 pm-11:00 pm

1 stop3h 18m

$159

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Tue 2/4

6:00 am-11:59 am

1 stop6h 59m

Chicago Midway

Mon 2/10

6:00 am-12:32 pm

1 stop5h 32m

$217

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Sun 3/9

5:25 pm-7:50 am

1 stop15h 25m

Chicago Midway

Tue 3/11

6:36 pm-9:17 am

1 stop13h 41m

$253

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/11

6:10 am-11:59 am

1 stop6h 49m

Chicago Midway

Tue 2/18

5:05 pm-12:09 am

1 stop6h 04m

$277

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 3/7

2:59 pm-11:58 pm

1 stop9h 59m

Chicago Midway

Mon 3/24

6:20 am-1:59 pm

1 stop6h 39m

$280

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Wed 2/26

5:55 am-7:40 am

Nonstop2h 45m

Chicago Midway

Thu 2/27

8:20 pm-11:30 pm

Nonstop2h 10m

$285

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 32 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 November is currently the most expensive (average of $249). 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 January 21, 2025.

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 January 21, 2025.
To help decide which airline to fly from Connecticut to Chicago, see what other customers have to say about Frontier, Delta 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
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

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
4,662 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

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
8,521 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

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
3,443 reviews
Southwest
8.1
Very good
4,662 reviews

Food

7.2

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.7

Overall

8.1

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 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 $59 on Frontier. Other airlines that offer cheap prices include Southwest from $74 and Delta from $84 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 $168. On average you can expect to pay $364. The most popular route, (Newark - Chicago Midway), can usually be booked for $128.

  • 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 November is currently the most expensive (average of $249). 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.

See more FAQs

Traveling to a place near Connecticut?

Book flights to Connecticut if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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.
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Dallas/Fort Worth to Midway flights
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Philadelphia to Midway flights
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Hobby to Midway flights
George Bush Intcntl to O'Hare Intl flights
Nashville to O'Hare Intl flights
Boston to Midway flights
Detroit to O'Hare Intl flights
Portland to O'Hare Intl flights
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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 2,558,603 searches. Data last updated January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$253FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$364FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$364FlexibilityNo cancel feeOn-time63%
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