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$162+ Cheap flights from Midway (MDW) to Hartford (BDL)

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 8/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — BDL
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from Midway to Hartford

Cheapest flights from Midway to Hartford
Explore the most affordable flight options available from Midway to Hartford. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Southwest deal was found by Cheapflights users on 7/24. 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 9/88:45 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Tue 9/1512:45 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/24$277
This Southwest deal was found by Cheapflights users on 7/24. 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 9/91:00 pm
MDW
-
BDL
Nonstop2h 05m
Southwest
Fri 9/116:20 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/24$282
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:55 pm
MDW
-
BDL
1 stop10h 10m
Southwest
Mon 10/127:05 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/22$293
This Southwest deal was found by Cheapflights users on 7/25. 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 8/157:50 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Mon 8/176:20 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/25$296
This Delta deal was found by Cheapflights users on 7/26. 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 8/176:42 pm
MDW
-
BDL
1 stop4h 09m
Delta
Wed 8/195:30 am
BDL
-
MDW
1 stop4h 47m
Delta
Deal found 7/26$297
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.
Fri 9/47:10 pm
MDW
-
BDL
Nonstop2h 10m
Southwest
Mon 9/76:20 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/23$300
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:45 am
MDW
-
BDL
Nonstop2h 15m
Southwest
Mon 8/175:00 pm
BDL
-
MDW
1 stop6h 20m
Southwest
Deal found 7/22$301
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.
Fri 9/47:10 pm
MDW
-
BDL
Nonstop2h 10m
Southwest
Sun 9/66:15 pm
BDL
-
MDW
Nonstop2h 20m
Southwest
Deal found 7/23$305

Find flight deals from Midway to Hartford

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Hartford (BDL). 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 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(Southwest)

One-way from

$162
(Southwest)

Popular in

July

Cheapest in

October

Average price

$503
Provider with most accurate pricing for Chicago Midway-Hartford Bradley Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Hartford Bradley Intl flights.
Search Deals
From Chicago Midway to Hartford Bradley Intl
Search Deals
One-way flight from Chicago Midway to Hartford Bradley Intl
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($58 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 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 Midway to Hartford 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 27, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Hartford that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Thu 9/17

8:45 am-12:00 pm

Nonstop2h 15m

Hartford Bradley Intl

Tue 9/22

5:55 pm-7:15 pm

Nonstop2h 20m

$277
Quickest round-trip

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 9/9

1:00 pm-4:05 pm

Nonstop2h 05m

Hartford Bradley Intl

Wed 9/16

6:10 pm-7:30 pm

Nonstop2h 20m

$277

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 9/30

7:30 am-4:55 pm

1 stop8h 25m

Hartford Bradley Intl

Thu 10/1

7:05 pm-8:25 pm

Nonstop2h 20m

$287

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 8/22

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Mon 8/24

5:16 pm-10:36 pm

1 stop6h 20m

$297

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 9/8

9:00 am-5:10 pm

2 stops7h 10m

Hartford Bradley Intl

Tue 9/15

12:40 pm-6:45 pm

1 stop7h 05m

$302

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 10/10

9:55 am-3:00 pm

1 stop4h 05m

Hartford Bradley Intl

Sat 10/17

9:35 am-6:00 pm

2 stops9h 25m

$302

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Wed 8/26

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Sat 8/29

1:09 pm-6:33 pm

1 stop6h 24m

$307

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Tue 8/25

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Sat 8/29

1:09 pm-6:33 pm

1 stop6h 24m

$307

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Sat 8/15

6:42 pm-11:51 pm

1 stop4h 09m

Hartford Bradley Intl

Sat 8/22

5:30 am-9:17 am

1 stop4h 47m

$307

ChicagoHartford

MDW - BDL

MDWBDL

Chicago Midway

Fri 10/9

6:45 pm-9:50 pm

Nonstop2h 05m

Hartford Bradley Intl

Tue 10/13

5:35 am-11:20 am

1 stop6h 45m

$310

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

Showing 1-10 of 21 resultsSorted by cheapest first
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Compare providers for flights from Midway to Hartford

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 Midway to Hartford 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 Chicago Midway Airport-Hartford flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Hartford flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Hartford flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Hartford 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 Chicago Midway Airport-Hartford 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 Midway to Hartford

Have a flexible travel schedule? Discover the best time to fly to Hartford 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.

Cheapflights Insights

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

What is the cheapest time of day to fly from MDW to BDL?

Find hourly flight availability from Midway to Hartford. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

A simple way to save on the total cost of your ticket is to fly from Chicago Midway Airport to Hartford in the morning. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight in the evening.

Reviews of airlines servicing Hartford

Get insights into the airlines that provide service to Hartford. 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 Hartford. Reviews last updated July 27, 2026.
Read through reviews of airlines operating flights from Chicago Midway Airport to Hartford, 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
4,232 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.
Southwest
8.0
Very good
4,232 reviews
Southwest
8.0
Very good
4,232 reviews

Food

7.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Feb 2026

DEN - BDL

Weird they cancelled a direct and rerouted me on a connecting flight to get in 10 hours later. What was the point? Crew and flight were great, but not sure what's going on with Southwest.

Related info for your journey

Find useful and relevant information for your journey from Midway to Hartford. 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 into for flights to Hartford from Chicago Midway?

    Hartford Bradley Intl (BDL) is the airport you will fly into if you book a flight from Chicago Midway to Hartford. You should not have trouble finding flights to Bradley Intl from Chicago Midway; the airport handles an average of 1 inbound flight from Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights to the Hartford airport from Chicago Midway. It is only a 11.9 mi journey from Bradley Intl (BDL) to Hartford’s city center.

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

    For as low as $277, Southwest can have you in Hartford from Chicago Midway Airport in 2h 15m. Chicago Midway Airport and Hartford are separated by a distance of 773 mi. Most flights are nonstop.

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

    Cheapflights users have booked flights from Chicago Midway Airport to Hartford round-trip from $248. Southwest is priced at 39% lower than the current average price of a flight leaving 3 months from now.

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

    On average you can expect to pay $323 for a flight from Chicago Midway Airport to Hartford. The cheapest flight overall is $144 while the most popular route, (Chicago Midway - Hartford Bradley Intl) is currently priced at $277.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Hartford by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Hartford?

Book flights to Hartford if you plan to visit one of these locations
Uncasville
New Britain
West Springfield
Southington
Enfield
Windsor Locks
Cromwell
Newington
Windsor
Farmington
East Hartford
Northampton
Westfield
Rocky Hill
Glastonbury
Meriden
Lee
West Hartford

Browse thousands of different options on Cheapflights for your next trip

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Top airline flying from Midway to Hartford

Discover the top airline that operate flights from Midway to Hartford. 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 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$248Average$403FlexibilityNo cancel feeOn-time63%

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