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$112+ Cheap flights from Hartford (BDL) 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
1 adult, Economy
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Cheap flight deals from Hartford to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Hartford (BDL) 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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$225
(Southwest)

One-way from

$112
(eDestinos)

Popular in

March

Cheapest in

August

Average price

$399
Provider with most accurate pricing for Hartford Bradley Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Hartford Bradley Intl-Chicago Midway flights.
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From Hartford Bradley Intl to Chicago Midway
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One-way flight from Hartford Bradley Intl to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Hartford to Midway

Cheapest flights from Hartford to Midway
Explore the most affordable flight options available from Hartford to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 12, 2025.

This Southwest deal was found by Cheapflights users on 11/11. 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 12/117:25 amBDL - MDW
2 stops6h 35mSouthwest
Tue 12/1612:55 pmMDW - BDL
1 stop6h 10mSouthwest
Deal found 11/11$227
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:59 amBDL - MDW
1 stop27h 00mMultiple Airlines
Mon 12/86:15 amMDW - BDL
2 stops15h 37mMultiple Airlines
Deal found 11/11$228
This Mytrip deal was found by Cheapflights users on 11/9. 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 11/2311:42 amBDL - MDW
1 stop11h 51mFrontier
Thu 11/275:30 pmMDW - BDL
1 stop22h 47mFrontier
Deal found 11/9$229
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/255:42 pmBDL - MDW
1 stop24h 15mMultiple Airlines
Tue 12/27:44 amMDW - BDL
2 stops28h 58mMultiple Airlines
Deal found 11/11$234
This Southwest deal was found by Cheapflights users on 11/10. 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 12/165:15 amBDL - MDW
Nonstop2h 30mSouthwest
Wed 12/1712:55 pmMDW - BDL
1 stop6h 10mSouthwest
Deal found 11/10$235
This Kiwi.com deal was found by Cheapflights users on 11/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/51:19 pmBDL - MDW
1 stop10h 20mMultiple Airlines
Sun 12/76:37 pmMDW - BDL
2 stops27h 15mMultiple Airlines
Deal found 11/10$242
This Delta deal was found by Cheapflights users on 11/11. 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 12/177:30 amBDL - MDW
1 stop5h 25mDelta
Sun 1/186:14 pmMDW - BDL
1 stop4h 26mDelta
Deal found 11/11$245
This Mytrip deal was found by Cheapflights users on 11/11. 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 11/2010:54 amBDL - MDW
1 stop12h 49mFrontier
Sat 11/226:02 pmMDW - BDL
1 stop24h 30mFrontier
Deal found 11/11$251
This Mytrip deal was found by Cheapflights users on 11/10. 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 12/511:59 amBDL - MDW
1 stop11h 13mFrontier
Sun 12/76:37 pmMDW - BDL
1 stop17h 35mFrontier
Deal found 11/10$252
This Delta deal was found by Cheapflights users on 11/10. 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 12/61:01 pmBDL - MDW
1 stop6h 05mDelta
Sun 12/76:40 pmMDW - BDL
1 stop3h 58mDelta
Deal found 11/10$255

Cheapflights Fare Finder

 
Customize your flight search to find flights from Hartford 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 November 12, 2025.
Use the filters below to find and compare flights from Hartford to Chicago Midway Airport that are best for you.

Fly from

Hartford

Fly to

Midway

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 2/22

5:10 am-6:45 am

Nonstop2h 35m

Chicago Midway

Sat 2/28

6:05 pm-9:05 pm

Nonstop2h 00m

$225

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/11

7:25 am-1:00 pm

2 stops6h 35m

Chicago Midway

Tue 12/16

12:55 pm-8:05 pm

1 stop6h 10m

$227

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 1/8

5:30 am-7:05 am

Nonstop2h 35m

Chicago Midway

Sat 1/10

6:40 am-11:55 am

1 stop4h 15m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/16

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Wed 12/17

12:55 pm-8:05 pm

1 stop6h 10m

$235

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 11/24

12:10 pm-4:39 pm

1 stop5h 29m

Chicago Midway

Tue 12/2

6:40 pm-11:38 pm

1 stop3h 58m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/3

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Wed 3/4

9:34 am-4:22 pm

1 stop5h 48m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 12/5

11:59 am-10:12 pm

1 stop11h 13m

Chicago Midway

Sun 12/7

6:37 pm-1:12 pm

1 stop17h 35m

$252

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/30

5:30 am-8:49 am

1 stop4h 19m

Chicago Midway

Tue 1/6

9:34 am-4:09 pm

1 stop5h 35m

$280

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/17

6:00 pm-7:35 pm

Nonstop2h 35m

$147

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 2/3

5:30 am-7:05 am

Nonstop2h 35m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 19 results
1
2

Compare providers for flights from Hartford to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Hartford to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Hartford-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Hartford-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Hartford-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Hartford-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Hartford-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Hartford to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Hartford 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 Hartford to Chicago Midway Airport

What is the cheapest month to book a flight from Hartford to Chicago Midway Airport?

Currently, August is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $170). Flying from Hartford to Chicago Midway Airport in January is currently the most expensive (average of $447). 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 BDL to MDW?

Find hourly flight availability from Hartford 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 12, 2025.

A simple way to save on the total cost of your ticket is to fly from Hartford to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 10% on your trip compared to booking a flight in the evening.

What is the cheapest day to fly from Hartford to Chicago Midway Airport?

Use this chart to determine the cheapest time to fly round-trip from Hartford to Midway. Price data was last updated on November 2, 2025.

Travelers seeking maximum savings on their Hartford to Chicago Midway Airport flight should consider departing on Wednesday at noon when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 12, 2025.
Read through reviews of airlines operating flights from Hartford to Chicago Midway Airport, such as Southwest and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,015 reviews
Southwest
8.0
Very good
4,235 reviews

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Hartford to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Hartford to Chicago Midway?

    Hartford Bradley Intl (BDL), located 11.9 mi from the city center, is the airport you fly out of when you book flights from Hartford to Chicago Midway. 2 airlines have flights from Bradley Intl to Chicago Midway on a regular basis. Booking flights from Hartford Bradley Intl to Chicago Midway should not be difficult; the airport handles an average of 2 outbound flights to Chicago Midway per day.

  • How long is the flight from Hartford to Chicago Midway Airport?

    A quick flight from Hartford to Chicago Midway Airport can take about 2h 35m. Southwest provides one of the quickest options available for as low as $225. The distance between Hartford and Chicago Midway Airport is about 773 mi. Most flights are nonstop.

  • What are the cheapest airlines flying from Hartford to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $177. Another option worth looking into is United Airlines, starting at $299 round trip. Southwest is currently priced 52% below the average price you’ll pay for this route.

  • What are the cheapest flights from Hartford to Chicago Midway Airport?

    The cheapest flight price from Hartford to Chicago Midway Airport is $123. On average you can expect to pay $349. The most popular route, (Hartford Bradley Intl - Chicago Midway), can usually be booked for $157.

  • Can I find deals for flights from Hartford to Midway that include hotel bookings?

    Yes. In addition to deals on Hartford to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Hartford to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Hartford to Midway.

  • Can I find deals for business class flights from Hartford to Midway?

    Yes. Cheapflights offers flight deals from Hartford 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 Hartford to Chicago Midway Airport?

    Currently, August is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $170). Flying from Hartford to Chicago Midway Airport in January is currently the most expensive (average of $447). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Hammond
Porter
Benton Harbor
Merrillville

Browse thousands of different options on Cheapflights for your next trip

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Top 2 airlines flying from Hartford to Midway

Discover the top 2 airlines that operate flights from Hartford 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 November 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$177Average$383FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$299Average$471FlexibilityNo cancel feeOn-time69%

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