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$53+ 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Nov 10 — Nov 171
Sun 11/10
Sun 11/17
1 adult, Economy
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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 November 5, 2024.

This Mytrip deal was found by Cheapflights users on 11/4. 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 12/53:00 pmJFK - MDW
1 stop23h 54mFrontier
Mon 12/911:33 amMDW - JFK
1 stop25h 26mFrontier
Deal found 11/4$106
This Frontier deal was found by Cheapflights users on 11/5. 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 12/75:11 pmLGA - MDW
1 stop7h 18mFrontier
Mon 12/97:15 amMDW - LGA
1 stop13h 45mFrontier
Deal found 11/5$106
This Kissandfly.com deal was found by Cheapflights users on 11/5. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/75:11 pmLGA - MDW
1 stop7h 18mMultiple Airlines
Mon 12/96:17 pmMDW - LGA
2 stops22h 42mMultiple Airlines
Deal found 11/5$142
This Southwest deal was found by Cheapflights users on 11/5. 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
Mon 12/97:55 pmMDW - LGA
Nonstop2h 05mSouthwest
Deal found 11/5$148
This Delta deal was found by Cheapflights users on 11/5. 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 12/76:00 amEWR - MDW
1 stop3h 58mDelta
Tue 12/101:30 pmMDW - EWR
1 stop5h 02mDelta
Deal found 11/5$166
This Mytrip deal was found by Cheapflights users on 11/3. 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 12/206:05 pmBDL - MDW
1 stop6h 09mFrontier
Wed 12/258:25 amMDW - BDL
1 stop5h 45mFrontier
Deal found 11/3$215
This KAYAK deal was found by Cheapflights users on 11/5. 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.
Wed 11/1311:46 amJFK - MDW
1 stop7h 46mDelta
Fri 11/155:42 pmMDW - JFK
1 stop4h 43mDelta
Deal found 11/5$286
This eDestinos deal was found by Cheapflights users on 11/3. 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 11/79:55 amEWR - MDW
1 stop22h 47mMultiple Airlines
Thu 11/146:00 amMDW - EWR
1 stop14h 29mMultiple Airlines
Deal found 11/3$294
This Delta deal was found by Cheapflights users on 11/4. 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 11/235:05 amPVD - MDW
1 stop4h 45mDelta
Sun 11/249:31 amMDW - PVD
1 stop5h 44mDelta
Deal found 11/4$298
This Southwest deal was found by Cheapflights users on 11/4. 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 11/235:05 amPVD - MDW
Nonstop2h 40mSouthwest
Sun 11/248:20 pmMDW - PVD
Nonstop2h 10mSouthwest
Deal found 11/4$310
This Southwest deal was found by Cheapflights users on 11/5. 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 11/235:15 amBDL - MDW
Nonstop2h 35mSouthwest
Sun 11/248:15 amMDW - BDL
1 stop4h 20mSouthwest
Deal found 11/5$333
This Delta deal was found by Cheapflights users on 11/4. 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 12/247:30 amBDL - MDW
1 stop8h 04mDelta
Tue 12/316:00 amMDW - BDL
1 stop5h 55mDelta
Deal found 11/4$342

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 2,554,862 searches. Data last updated November 5, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Wed 11/13

12:29 pm-12:13 pm

1 stop24h 44m

$53

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Sat 12/7

6:30 am-8:00 am

Nonstop2h 30m

$74

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 1/9

9:37 am-1:08 pm

1 stop4h 31m

$83

NewarkChicago

EWR - MDW

EWRMDW

Newark

Mon 1/13

9:15 am-11:24 pm

1 stop15h 09m

$95

New YorkChicago

JFK - MDW

JFKMDW

New York John F Kennedy Intl

Sat 11/23

11:00 am-9:22 pm

1 stop11h 22m

$54

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 12/9

2:17 pm-11:21 pm

1 stop10h 04m

$79

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 11/14

10:55 am-8:04 pm

1 stop10h 09m

$184

NewarkChicago

EWR - MDW

EWRMDW

Newark

Thu 11/28

11:15 am-4:40 pm

1 stop6h 25m

$215

NewarkChicago

EWR - MDW

EWRMDW

Newark

Tue 11/19

10:00 pm-11:04 am

1 stop14h 04m

$89

New YorkChicago

LGA - MDW

LGAMDW

New York LaGuardia

Tue 12/31

3:25 pm-1:24 pm

2 stops22h 59m

$112

Flights are sorted by cheapest first

Deals found on 11/4

Showing 1-10 of 37 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 $159). Flying from Connecticut to Chicago Midway Airport in July is currently the most expensive (average of $231). 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 5, 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 5, 2024.
To help decide which airline to fly from Connecticut to Chicago, see what other customers have to say about Frontier, Porter Airlines 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
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Southwest
8.1
Very good
5,082 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Delta
8.0
Very good
8,830 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Porter Airlines
7.8
Good
292 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

Air Transat
7.8
Good
387 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

Reviews

1 / 10

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

WestJet
7.3
Good
2,800 reviews
Southwest
8.1
Very good
5,082 reviews

Crew

8.7

Entertainment

7.7

Overall

8.1

Comfort

8.1

Boarding

8.3

Food

7.2

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.

  • Can I find flights from Connecticut to Chicago Midway Airport for under $200 on Cheapflights?

    Yes, there are multiple flights from Connecticut to Chicago Midway Airport for under $200. The cheapest flight booked recently is on Frontier for just $105, but on average you can expect to pay $268.

  • Are there nonstop flights from Connecticut to Chicago Midway Airport for under $200 on Cheapflights?

    Cheapflights has at least 3 direct flights from Connecticut to Chicago Midway Airport under $200. A good price for a nonstop flight from Connecticut to Chicago Midway Airport is less than $272.

  • Are there last-minute flights available from Connecticut to Chicago Midway Airport for under $200?

    There are currently 16+ open flights from Connecticut to Chicago Midway Airport within the next 7 days for less than $200.

  • 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 $53 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 New York John F Kennedy Intl - Chicago Midway, Newark - 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 $354. The most popular route, (New York John F Kennedy Intl - Chicago Midway), can usually be booked for $119.

  • What does BDL to MDW mean?

    Great question - BDL to MDW just means Hartford Bradley Intl Airport to Chicago Midway Airport. Now you’ll know what these unique codes when you look for flights!

  • Can I find deals for flights from Connecticut to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Connecticut to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Connecticut to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Connecticut to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Connecticut to Midway that allow pets onboard?

    Many airlines flying from Connecticut to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Connecticut to Midway?

    Yes, you can often find last-minute deals on Connecticut to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Connecticut to Chicago Midway Airport flight deals updated?

    The Connecticut to Chicago Midway Airport flight deals you see on this page were last updated on 11/5.

  • 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 $159). Flying from Connecticut to Chicago Midway Airport in July is currently the most expensive (average of $231). 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

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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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Hartford to O'Hare Intl flights
Dulles Intl to Midway flights
San Jose to O'Hare Intl flights
Cleveland to O'Hare Intl flights
Columbus to O'Hare Intl flights
Love Field to O'Hare Intl flights
George Bush Intcntl to Midway flights
Kansas City to O'Hare Intl flights
Nashville to O'Hare Intl flights
Reagan-National 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 2,554,862 searches. Data last updated November 5, 2024.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$117Average$314FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$148Average$239FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$383FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$273Average$342FlexibilityNo cancel feeOn-time63%
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