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$52+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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Cheap flight deals from Connecticut to Midway

Keep the following information in mind while searching for Connecticut to Midway flight deals. Data was last updated febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$98
(Cheapflightsfares)

One-way from

$52
(Mytrip)

Good round-trip deal

$393 or less

Good one-way deal

$171 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
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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 febrero 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/19. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/2511:01 amJFK - MDW
1 stop5h 52mFrontier
mar. 4/14:40 pmMDW - JFK
1 stop7h 03mFrontier
Deal found 2/19$98
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/14:00 pmLGA - MDW
1 stop7h 04mFrontier
mar. 3/117:50 amMDW - LGA
1 stop12h 09mFrontier
Deal found 2/19$100
This Frontier deal was found by Cheapflights users on 2/20. 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.
lun. 4/710:00 pmEWR - MDW
1 stop12h 11mFrontier
mar. 4/82:45 pmMDW - EWR
1 stop5h 15mFrontier
Deal found 2/20$104
This Southwest deal was found by Cheapflights users on 2/20. 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.
jue. 5/19:45 pmLGA - MDW
Nonstop2h 15mSouthwest
jue. 5/86:10 amMDW - LGA
Nonstop2h 00mSouthwest
Deal found 2/20$147
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 4/229:33 amEWR - MDW
1 stop4h 02mDelta
mar. 4/295:59 pmMDW - EWR
1 stop4h 00mDelta
Deal found 2/20$167
This Southwest deal was found by Cheapflights users on 2/20. 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.
mié. 4/301:25 pmBDL - MDW
2 stops8h 45mSouthwest
vie. 5/29:50 amMDW - BDL
1 stop5h 25mSouthwest
Deal found 2/20$222
This Delta deal was found by Cheapflights users on 2/20. 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.
mar. 3/257:15 amJFK - MDW
1 stop11h 47mDelta
jue. 3/279:25 amMDW - JFK
1 stop8h 15mDelta
Deal found 2/20$233
This Delta deal was found by Cheapflights users on 2/20. 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.
sáb. 4/266:05 amLGA - MDW
1 stop7h 30mDelta
lun. 4/283:02 pmMDW - LGA
1 stop7h 37mDelta
Deal found 2/20$233
This Delta deal was found by Cheapflights users on 2/20. 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.
vie. 4/255:40 amBDL - MDW
1 stop4h 00mDelta
lun. 4/285:59 pmMDW - BDL
1 stop4h 11mDelta
Deal found 2/20$237
This Frontier deal was found by Cheapflights users on 2/20. 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.
vie. 4/183:13 pmBDL - MDW
1 stop9h 37mFrontier
lun. 4/217:05 amMDW - BDL
1 stop6h 20mFrontier
Deal found 2/20$240
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/169:55 amEWR - MDW
1 stop5h 08mAllegiant Air
vie. 6/2010:34 amMDW - EWR
1 stop21h 31mAllegiant Air
Deal found 2/19$281
This Southwest deal was found by Cheapflights users on 2/20. 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.
lun. 3/106:30 pmPVD - MDW
Nonstop2h 35mSouthwest
jue. 3/1310:45 pmMDW - PVD
Nonstop2h 10mSouthwest
Deal found 2/20$285

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 febrero 20, 2025.

Fly from

Connecticut

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

mar. 3/25

11:01 am-3:53 pm

1 stop5h 52m

Chicago Midway

mar. 4/1

4:40 pm-12:43 am

1 stop7h 03m

$98

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

sáb. 3/1

4:00 pm-10:04 pm

1 stop7h 04m

Chicago Midway

sáb. 3/8

12:45 pm-10:00 pm

1 stop8h 15m

$100

NewarkChicago

EWR - MDW

EWRMDW

Newark

lun. 4/7

10:00 pm-9:11 am

1 stop12h 11m

Chicago Midway

mar. 4/8

2:45 pm-9:00 pm

1 stop5h 15m

$104

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

jue. 5/1

6:30 am-7:50 am

Nonstop2h 20m

Chicago Midway

lun. 5/5

7:50 pm-11:00 pm

Nonstop2h 10m

$147

NewarkChicago

EWR - MDW

EWRMDW

Newark

mar. 4/22

9:33 am-12:35 pm

1 stop4h 02m

Chicago Midway

mar. 4/29

5:59 pm-10:59 pm

1 stop4h 00m

$167

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mié. 4/30

1:25 pm-9:10 pm

2 stops8h 45m

Chicago Midway

vie. 5/2

9:50 am-4:15 pm

1 stop5h 25m

$222

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

mar. 3/25

7:15 am-6:02 pm

1 stop11h 47m

Chicago Midway

mié. 3/26

2:55 pm-9:00 am

1 stop17h 05m

$223

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

sáb. 4/26

6:05 am-12:35 pm

1 stop7h 30m

Chicago Midway

lun. 4/28

3:02 pm-11:39 pm

1 stop7h 37m

$233

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

vie. 4/25

5:40 am-8:40 am

1 stop4h 00m

Chicago Midway

lun. 4/28

5:59 pm-11:10 pm

1 stop4h 11m

$237

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

vie. 4/18

3:13 pm-11:50 pm

1 stop9h 37m

Chicago Midway

lun. 4/21

7:05 am-2:25 pm

1 stop6h 20m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 febrero 20, 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 febrero 20, 2025.
To help decide which airline to fly from Connecticut to Chicago, 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
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Allegiant Air
7.3
Good
765 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Frontier
6.0
Okay
3,355 reviews
Southwest
8.1
Very good
4,411 reviews

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $52 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 $128. On average you can expect to pay $332. The most popular route, (Newark - Chicago Midway), can usually be booked for $78.

  • 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.
John F Kennedy Intl to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Dulles Intl to O'Hare Intl flights
Boston to O'Hare Intl flights
Seattle to O'Hare Intl flights
Baltimore to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Reagan-National to O'Hare Intl flights
Newark to Midway flights
John F Kennedy Intl to Midway flights
Philadelphia to O'Hare Intl flights
Denver to O'Hare Intl flights
Sky Harbor Intl to O'Hare Intl flights
Minneapolis to O'Hare Intl flights
Dallas/Fort Worth to Midway flights
LaGuardia to Midway flights
Los Angeles to Midway flights
Baltimore to Midway flights
Austin to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
Atlanta to O'Hare Intl flights
Reagan-National to Midway flights
Raleigh to O'Hare Intl flights
Burbank to O'Hare Intl flights
San Diego to O'Hare Intl flights
Dulles Intl to Midway flights
Charlotte to O'Hare Intl flights
San Francisco to Midway flights
Orlando to O'Hare Intl flights
Love Field to O'Hare Intl flights
Miami to O'Hare Intl flights
Seattle to Midway flights
Atlanta to Midway flights
Portland to O'Hare Intl flights
George Bush Intcntl to O'Hare Intl flights
Minneapolis to Midway flights
Philadelphia to Midway flights
Tampa to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Hobby to O'Hare Intl flights
Oakland to O'Hare Intl flights
Denver to Midway flights
Hobby to Midway flights
Nashville to O'Hare Intl flights
Hartford to O'Hare Intl 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 2,558,603 searches. Data last updated febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$204FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$153Average$257FlexibilityNo cancel feeOn-time62%
DeltaCheapest$175Average$358FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$257Average$377FlexibilityNo cancel feeOn-time63%
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