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Midway

$153+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Aug 23 — Aug 301
Sun 8/23
Sun 8/30
1 adult, Economy
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Cheap 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 July 24, 2026.

This Southwest deal was found by Cheapflights users on 7/23. 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 8/253:05 pm
BDL
-
MDW
1 stop6h 40m
Southwest
Mon 8/318:45 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Deal found 7/23$287
This Southwest deal was found by Cheapflights users on 7/21. 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 10/16:50 am
BDL
-
MDW
Nonstop2h 20m
Southwest
Thu 10/88:55 pm
MDW
-
BDL
1 stop10h 10m
Southwest
Deal found 7/21$293
This Southwest deal was found by Cheapflights users on 7/21. 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.
Wed 9/212:45 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Fri 9/47:10 pm
MDW
-
BDL
Nonstop2h 05m
Southwest
Deal found 7/21$295
This Delta deal was found by Cheapflights users on 7/23. 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.
Mon 8/245:16 pm
BDL
-
MDW
1 stop6h 20m
Delta
Mon 8/315:45 pm
MDW
-
BDL
1 stop5h 06m
Delta
Deal found 7/23$297
This Southwest deal was found by Cheapflights users on 7/21. 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.
Fri 10/2312:30 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Mon 10/2612:45 pm
MDW
-
BDL
Nonstop2h 05m
Southwest
Deal found 7/21$300
This Southwest deal was found by Cheapflights users on 7/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/31:40 pm
BDL
-
MDW
Nonstop2h 15m
Southwest
Sun 9/68:55 am
MDW
-
BDL
1 stop7h 15m
Southwest
Deal found 7/19$301
This Southwest deal was found by Cheapflights users on 7/21. 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 8/2710:15 am
BDL
-
MDW
1 stop4h 50m
Southwest
Mon 8/315:30 am
MDW
-
BDL
2 stops6h 30m
Southwest
Deal found 7/21$302
This Southwest deal was found by Cheapflights users on 7/20. 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.
Sat 8/227:55 am
BDL
-
MDW
Nonstop2h 20m
Southwest
Thu 8/278:45 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Deal found 7/20$305
This Southwest deal was found by Cheapflights users on 7/23. 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 8/198:10 am
BDL
-
MDW
2 stops8h 15m
Southwest
Thu 8/208:45 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Deal found 7/23$306
This Delta deal was found by Cheapflights users on 7/22. 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 8/199:43 am
BDL
-
MDW
1 stop3h 56m
Delta
Tue 8/255:10 pm
MDW
-
BDL
1 stop5h 48m
Delta
Deal found 7/22$307

Find 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 July 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(Southwest)

One-way from

$153
(Southwest)

Popular in

April

Cheapest in

January

Average price

$437
Provider with most accurate pricing for Hartford Bradley Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Hartford Bradley Intl-Chicago Midway flights.
Search Deals
From Hartford Bradley Intl to Chicago Midway
Search Deals
One-way flight from Hartford Bradley Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 29% potential increase in price ($177 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 24, 2026.
Use the filters below to find and compare flights from Hartford to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 9/26

5:50 am-1:05 pm

2 stops8h 15m

Chicago Midway

Wed 9/30

8:45 am-12:00 pm

Nonstop2h 15m

$292

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 11/6

12:55 pm-2:25 pm

Nonstop2h 30m

Chicago Midway

Mon 11/9

7:10 pm-10:10 pm

Nonstop2h 00m

$300

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/21

5:35 am-12:25 pm

2 stops7h 50m

Chicago Midway

Sat 10/24

8:40 am-3:25 pm

1 stop5h 45m

$302

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/24

10:15 am-4:15 pm

1 stop7h 00m

Chicago Midway

Mon 9/28

5:30 am-1:00 pm

2 stops6h 30m

$302
Quickest round-trip

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 9/3

6:20 pm-7:40 pm

Nonstop2h 20m

Chicago Midway

Mon 9/7

7:10 pm-10:15 pm

Nonstop2h 05m

$305

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 8/19

8:10 am-3:25 pm

2 stops8h 15m

Chicago Midway

Thu 8/20

8:45 am-12:00 pm

Nonstop2h 15m

$306

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 8/12

12:45 pm-2:05 pm

Nonstop2h 20m

Chicago Midway

Mon 8/17

8:00 am-3:05 pm

1 stop6h 05m

$315

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 8/16

5:30 am-9:17 am

1 stop4h 47m

Chicago Midway

Tue 8/18

6:05 am-12:48 pm

1 stop5h 43m

$320

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 10/4

6:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

Thu 10/8

8:55 pm-8:10 am

1 stop10h 15m

$325

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 11/6

12:55 pm-2:25 pm

Nonstop2h 30m

Chicago Midway

Sun 11/8

5:05 am-12:05 pm

1 stop6h 00m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/22

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Hartford-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, January is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $176). Flying from Hartford to Chicago Midway Airport in April is currently the most expensive (average of $892). 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 July 24, 2026.

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 17% on your trip compared to booking a flight in the morning.

How much does it cost to fly round-trip from Hartford to Chicago Midway Airport?

Airfare is below average for this route at the moment.

Hartford to Chicago Midway Airport flights typically cost between $318 and $482 in October.
The cheapest round-trip price found within the last 5 days was $282 on Southwest (Oct 30-Nov 2).

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 July 24, 2026.
Read through reviews of airlines operating flights from Hartford to Chicago Midway Airport, such as Southwest. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers
Southwest
8.0
Very good
4,236 reviews
Southwest
8.0
Very good
4,236 reviews

Crew

8.6

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Reviews

1 / 20
6.0
Good

Reza,Jun 2026

TPA - MDW

The seats were super cramped and couldn’t move without hitting other passengers

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. 1 airline 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 8h 15m. Southwest provides one of the quickest options available for as low as $292. The distance between Hartford and Chicago Midway Airport is about 773 mi.

  • What is the cheapest airline to fly from Hartford to Chicago Midway Airport round-trip?

    Flying on Southwest is currently your cheapest option to Chicago Midway Airport, with prices starting at $237. Southwest is currently priced 44% 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 $164. On average you can expect to pay $387. The most popular route, (Hartford Bradley Intl - Chicago Midway), can usually be booked for $277.

  • 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, January is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $176). Flying from Hartford to Chicago Midway Airport in April is currently the most expensive (average of $892). 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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Hartford to Midway

Discover the top airline 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 July 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$237Average$414FlexibilityNo cancel feeOn-time63%

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