HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Connecticut

$55+ 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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Connecticut 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 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 January 21, 2025.

Round-trip from

$105
(Frontier)

One-way from

$55
(Frontier)

Good round-trip deal

$330 or less

Good one-way deal

$83 or less
From Chicago Midway to Connecticut
Search Deals
One-way flight from Chicago Midway to Connecticut
Search Deals
Price to beat on a round-trip flight from Chicago Midway to Connecticut.
Search Deals
Price to beat on a one-way flight from Chicago Midway to Connecticut.
Search Deals

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 January 21, 2025.

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.
Wed 2/198:12 amMDW - LGA
1 stop5h 48mFrontier
Wed 2/1910:00 pmLGA - MDW
1 stop14h 28mFrontier
Deal found 1/20$100
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.
Wed 4/303:20 pmMDW - JFK
1 stop8h 13mFrontier
Wed 5/76:00 amJFK - MDW
1 stop12h 18mFrontier
Deal found 1/20$110
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/198:12 amMDW - EWR
1 stop11h 58mFrontier
Mon 2/2410:10 pmEWR - MDW
1 stop10h 22mFrontier
Deal found 1/21$122
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.
Tue 2/118:05 pmMDW - LGA
Nonstop2h 05mSouthwest
Wed 2/129:35 pmLGA - MDW
Nonstop2h 30mSouthwest
Deal found 1/20$147
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 3/15:05 pmMDW - EWR
1 stop5h 04mDelta
Tue 3/49:37 amEWR - MDW
1 stop4h 28mDelta
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.
Wed 2/1910:57 amMDW - PVD
1 stop5h 58mDelta
Wed 2/267:00 amPVD - MDW
1 stop7h 05mDelta
Deal found 1/20$217
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 2/195:05 pmMDW - PVD
1 stop4h 20mSouthwest
Wed 2/265:55 amPVD - MDW
Nonstop2h 45mSouthwest
Deal found 1/20$268
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/36:10 pmMDW - PVD
1 stop15h 22mMultiple Airlines
Sun 4/65:25 pmPVD - MDW
1 stop15h 20mMultiple Airlines
Deal found 1/20$269
This KAYAK deal was found by Cheapflights users on 1/19. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/286:28 pmMDW - JFK
1 stop3h 46mDelta
Thu 1/3012:59 pmJFK - MDW
1 stop6h 15mDelta
Deal found 1/19$281
This Frontier deal was found by Cheapflights users on 1/19. 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.
Thu 3/67:25 amMDW - BDL
1 stop9h 57mFrontier
Sun 3/911:52 amBDL - MDW
1 stop8h 37mFrontier
Deal found 1/19$320
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.
Thu 2/201:20 pmMDW - BDL
Nonstop2h 00mSouthwest
Sun 2/238:00 pmBDL - MDW
Nonstop2h 35mSouthwest
Deal found 1/21$325
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.
Mon 8/187:07 pmMDW - EWR
1 stop12h 58mAllegiant Air
Fri 8/229:55 amEWR - MDW
1 stop6h 07mAllegiant Air
Deal found 1/21$343

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

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Wed 2/19

8:12 am-3:00 pm

1 stop5h 48m

New York LaGuardia

Wed 2/26

10:00 pm-11:28 am

1 stop14h 28m

$105

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Tue 4/22

3:20 pm-12:33 am

1 stop8h 13m

New York John F Kennedy Intl

Wed 4/30

9:00 am-2:25 pm

1 stop6h 25m

$110

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Wed 2/19

8:12 am-9:10 pm

1 stop11h 58m

Newark

Mon 2/24

10:10 pm-7:32 am

1 stop10h 22m

$122

ChicagoNew York

MDW - LGA

MDWLGA

Chicago Midway

Sat 2/22

6:45 am-9:55 am

Nonstop2h 10m

New York LaGuardia

Tue 2/25

9:35 pm-11:05 pm

Nonstop2h 30m

$147

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Sat 3/1

5:05 pm-11:09 pm

1 stop5h 04m

Newark

Wed 3/12

9:32 am-12:36 pm

1 stop4h 04m

$159

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 2/19

10:57 am-5:55 pm

1 stop5h 58m

Providence-TFGreen

Wed 2/26

7:00 am-1:05 pm

1 stop7h 05m

$217

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Wed 2/19

5:05 pm-10:25 pm

1 stop4h 20m

Providence-TFGreen

Wed 2/26

5:55 am-7:40 am

Nonstop2h 45m

$268

ChicagoProvidence

MDW - PVD

MDWPVD

Chicago Midway

Thu 4/3

6:10 pm-10:32 am

1 stop15h 22m

Providence-TFGreen

Sun 4/6

5:25 pm-7:45 am

1 stop15h 20m

$269

ChicagoNew York

MDW - JFK

MDWJFK

Chicago Midway

Wed 2/5

5:05 pm-12:42 am

1 stop6h 37m

New York John F Kennedy Intl

Fri 2/7

12:59 pm-6:11 pm

1 stop6h 12m

$295

ChicagoNewark

MDW - EWR

MDWEWR

Chicago Midway

Fri 5/30

8:04 pm-11:05 am

1 stop14h 01m

Newark

Mon 6/2

9:55 am-6:10 pm

1 stop9h 15m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 33 results
1
2
3
4

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 January 21, 2025.

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

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

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

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

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

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

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.

Allegiant Air
7.4
Good
801 reviews
Southwest
8.1
Very good
4,662 reviews

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

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

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

Boarding

8.2

Entertainment

7.7

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 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 $55 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 $315, our data shows the cheapest flight currently is $128. When looking at the most popular route, (Chicago Midway - Newark), you can expect to pay $123 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, November is the cheapest month in which you can book a flight from Chicago Midway Airport to Connecticut (average of $287). Flying from Chicago Midway Airport to Connecticut in June is currently the most expensive (average of $357). 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

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 Midway to Connecticut

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Las Vegas flights
O'Hare Intl to Orlando flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to Tampa flights
O'Hare Intl to Denver flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Seattle flights
O'Hare Intl to LaGuardia flights
Midway to Sky Harbor Intl flights
O'Hare Intl to Boston flights
Midway to Las Vegas flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Newark flights
Midway to Orlando flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to Atlanta flights
Midway to Miami flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Austin flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to San Diego flights
Midway to Newark flights
Midway to Los Angeles flights
O'Hare Intl to Nashville flights
O'Hare Intl to West Palm Beach flights
Midway to Atlanta flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Baltimore flights
O'Hare Intl to Philadelphia flights
Midway to Hobby flights
Midway to Tampa flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Sarasota flights
O'Hare Intl to Charleston flights
O'Hare Intl to Reagan-National flights
Midway to John F Kennedy Intl flights
Midway to LaGuardia flights
Midway to Denver flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Hobby flights
O'Hare Intl to Ontario flights
Midway to Fort Myers flights
Midway to San Francisco flights
O'Hare Intl to Burbank flights

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 2,558,603 searches. Data last updated January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$84Average$168FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$191Average$369FlexibilityNo 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.