HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$69+ 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$143
(Southwest)

One-way from

$69
(Southwest)

Good round-trip deal

$365 or less

Good one-way deal

$165 or less
Provider with most accurate pricing for Springfield (SFY)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Springfield (SFY)-Chicago (CHI) flights.
Search Deals
From Connecticut to Chicago Midway
Search Deals
One-way flight from Connecticut to Chicago Midway
Search Deals
Price to beat on a round-trip flight from Connecticut to Chicago Midway.
Search Deals
Price to beat on a one-way flight from Connecticut to Chicago Midway.
Search Deals

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 March 31, 2025.

This Southwest deal was found by Cheapflights users on 3/30. 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.
Sun 4/206:10 amLGA - MDW
Nonstop2h 20mSouthwest
Tue 4/225:50 pmMDW - LGA
Nonstop2h 10mSouthwest
Deal found 3/30$143
This Delta deal was found by Cheapflights users on 3/30. 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 5/106:05 amEWR - MDW
1 stop8h 10mDelta
Tue 5/134:15 pmMDW - EWR
1 stop7h 52mDelta
Deal found 3/30$179
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Wed 5/146:00 amJFK - MDW
1 stop6h 26mFrontier
Wed 5/212:12 pmMDW - JFK
1 stop9h 08mFrontier
Deal found 3/30$196
This Frontier deal was found by Cheapflights users on 3/30. 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.
Mon 4/2810:00 pmEWR - MDW
1 stop12h 16mFrontier
Sun 5/118:30 amMDW - EWR
1 stop11h 31mFrontier
Deal found 3/30$198
This Frontier deal was found by Cheapflights users on 3/31. 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.
Wed 5/146:30 amLGA - MDW
1 stop5h 56mFrontier
Thu 5/151:19 pmMDW - LGA
1 stop6h 40mFrontier
Deal found 3/31$198
This Frontier deal was found by Cheapflights users on 3/30. 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 5/153:28 pmBDL - MDW
1 stop9h 11mFrontier
Sun 5/1810:55 amMDW - BDL
1 stop7h 19mFrontier
Deal found 3/30$228
This Mytrip deal was found by Cheapflights users on 3/30. 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.
Tue 6/1011:55 amEWR - MDW
1 stop28h 42mAllegiant Air
Fri 6/138:36 pmMDW - EWR
1 stop13h 29mAllegiant Air
Deal found 3/30$229
This Southwest deal was found by Cheapflights users on 3/30. 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.
Fri 5/306:50 amPVD - MDW
Nonstop2h 30mSouthwest
Mon 6/27:10 pmMDW - PVD
Nonstop2h 10mSouthwest
Deal found 3/30$282
This Delta deal was found by Cheapflights users on 3/30. 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 5/310:00 amJFK - MDW
1 stop13h 22mDelta
Wed 5/1410:25 amMDW - JFK
1 stop13h 32mDelta
Deal found 3/30$283
This Southwest deal was found by Cheapflights users on 3/31. 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 7/14:50 pmBDL - MDW
Nonstop2h 25mSouthwest
Sat 7/55:30 amMDW - BDL
1 stop5h 30mSouthwest
Deal found 3/31$283
This Delta deal was found by Cheapflights users on 3/31. 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 7/16:00 amBDL - MDW
1 stop6h 56mDelta
Sat 7/512:41 pmMDW - BDL
1 stop7h 10mDelta
Deal found 3/31$293
This Delta deal was found by Cheapflights users on 3/31. 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.
Sun 4/205:50 amPVD - MDW
1 stop3h 50mDelta
Mon 4/285:59 pmMDW - PVD
1 stop4h 14mDelta
Deal found 3/31$302

Cheapflights Fare Finder

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 March 31, 2025.
Use the filters below to find and compare flights from Connecticut to Chicago Midway Airport that are best for you.

Fly from

Connecticut

Fly to

Midway

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sun 4/20

6:10 am-7:30 am

Nonstop2h 20m

Chicago Midway

Tue 4/22

5:50 pm-9:00 pm

Nonstop2h 10m

$143

NewarkChicago

EWR - MDW

EWRMDW

Newark

Sat 5/10

6:05 am-1:15 pm

1 stop8h 10m

Chicago Midway

Tue 5/13

4:15 pm-1:07 am

1 stop7h 52m

$179

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Wed 5/14

6:00 am-11:26 am

1 stop6h 26m

Chicago Midway

Wed 5/21

2:12 pm-12:20 am

1 stop9h 08m

$196

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 4/28

10:00 pm-9:16 am

1 stop12h 16m

Chicago Midway

Sun 5/11

8:30 am-9:01 pm

1 stop11h 31m

$198

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 5/14

6:30 am-11:26 am

1 stop5h 56m

Chicago Midway

Thu 5/15

1:19 pm-8:59 pm

1 stop6h 40m

$198

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 5/15

3:28 pm-11:39 pm

1 stop9h 11m

Chicago Midway

Sun 5/18

10:55 am-7:14 pm

1 stop7h 19m

$228

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 6/10

11:55 am-3:37 pm

1 stop28h 42m

Chicago Midway

Fri 6/13

8:36 pm-11:05 am

1 stop13h 29m

$229

ProvidenceChicago

PVD - MDW

PVDMDW

Providence-TFGreen

Fri 5/30

6:50 am-8:20 am

Nonstop2h 30m

Chicago Midway

Mon 6/2

7:10 pm-10:20 pm

Nonstop2h 10m

$282

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 5/3

10:00 am-10:22 pm

1 stop13h 22m

Chicago Midway

Wed 5/14

10:25 am-12:57 am

1 stop13h 32m

$283

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/1

4:50 pm-6:15 pm

Nonstop2h 25m

Chicago Midway

Sat 7/5

5:30 am-12:00 pm

1 stop5h 30m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 34 results
1
2
3
4

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.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to Chicago Midway Airport

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 March 31, 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 March 31, 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
8.0
Very good
4,275 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Allegiant Air
7.3
Good
731 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Frontier
6.0
Okay
3,275 reviews
Southwest
8.0
Very good
4,275 reviews

Overall

8.0

Food

7.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.7

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $69 on Southwest. Other airlines that offer cheap prices include Delta from $79 and Frontier from $95 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 $149. On average you can expect to pay $317. The most popular route, (Newark - Chicago Midway), can usually be booked for $147.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Connecticut to Midway

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

Top 5 airlines flying from Connecticut to Midway

Discover the top 5 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$77Average$202FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$108Average$253FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$125Average$471FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$389FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.