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$99+ 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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
1 adult, Economy
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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago Midway are usually found in August or September, booked 7 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$189
(Gotogate)

One-way from

$99
(Delta)

Popular in

March

Cheapest in

August

Average price

$333
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. 10% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This Gotogate deal was found by Cheapflights users on 9/27. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/238:31 pmBDL - MDW
1 stop15h 46mFrontier
Mon 10/276:15 amMDW - BDL
1 stop7h 51mFrontier
Deal found 9/27$189
This Frontier deal was found by Cheapflights users on 9/29. 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.
Fri 10/174:20 pmBDL - MDW
1 stop8h 26mFrontier
Sat 10/1811:31 amMDW - BDL
2 stops20h 38mFrontier
Deal found 9/29$192
This Delta deal was found by Cheapflights users on 9/28. 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.
Thu 11/135:30 amBDL - MDW
1 stop4h 24mDelta
Sun 11/166:48 pmMDW - BDL
1 stop3h 34mDelta
Deal found 9/28$197
This Booking.com deal was found by Cheapflights users on 9/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/610:42 amBDL - MDW
1 stop8h 57mFrontier
Sun 11/910:12 amMDW - BDL
1 stop25h 29mFrontier
Deal found 9/28$202
This Booking.com deal was found by Cheapflights users on 9/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/104:20 pmBDL - MDW
1 stop8h 26mFrontier
Thu 10/1611:49 amMDW - BDL
1 stop21h 55mFrontier
Deal found 9/28$203
This Southwest deal was found by Cheapflights users on 9/27. 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 10/2812:55 pmBDL - MDW
Nonstop2h 25mSouthwest
Wed 10/296:10 pmMDW - BDL
Nonstop2h 05mSouthwest
Deal found 9/27$208
This Kiwi.com deal was found by Cheapflights users on 9/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/268:31 pmBDL - MDW
1 stop15h 46mFrontier
Fri 10/311:37 pmMDW - BDL
1 stop19h 25mFrontier
Deal found 9/26$220
This Southwest deal was found by Cheapflights users on 9/27. 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.
Sun 10/265:45 amBDL - MDW
Nonstop2h 25mSouthwest
Tue 10/287:55 amMDW - BDL
1 stop4h 20mSouthwest
Deal found 9/27$222
This Southwest deal was found by Cheapflights users on 9/27. 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 10/305:25 amBDL - MDW
Nonstop2h 25mSouthwest
Sat 11/112:50 pmMDW - BDL
Nonstop2h 00mSouthwest
Deal found 9/27$225

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 September 29, 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

Thu 11/13

5:30 am-8:54 am

1 stop4h 24m

Chicago Midway

Sun 11/16

6:48 pm-11:22 pm

1 stop3h 34m

$197

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 10/28

12:55 pm-2:20 pm

Nonstop2h 25m

Chicago Midway

Wed 10/29

6:10 pm-9:15 pm

Nonstop2h 05m

$208

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 10/29

4:15 pm-10:05 pm

2 stops6h 50m

Chicago Midway

Fri 10/31

6:15 am-12:05 pm

1 stop4h 50m

$233

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 11/12

5:40 pm-7:10 pm

Nonstop2h 30m

Chicago Midway

Sun 11/16

11:55 am-2:55 pm

Nonstop2h 00m

$253

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 12/4

5:23 am-8:54 am

1 stop4h 31m

Chicago Midway

Fri 12/5

9:34 am-4:25 pm

1 stop5h 51m

$270

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 12/10

6:00 am-11:55 am

1 stop6h 55m

Chicago Midway

Sat 12/13

9:29 am-4:25 pm

1 stop5h 56m

$286

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 10/31

12:10 pm-6:50 pm

2 stops7h 40m

Chicago Midway

Sun 11/2

5:05 am-11:45 am

1 stop5h 40m

$290

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 11/13

2:00 pm-8:30 pm

2 stops7h 30m

Chicago Midway

Sun 11/16

5:05 am-11:45 am

1 stop5h 40m

$297

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 11/11

12:10 pm-7:35 pm

2 stops8h 25m

Chicago Midway

Sun 11/16

5:05 am-11:45 am

1 stop5h 40m

$297

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 12/16

5:42 pm-11:32 pm

1 stop6h 50m

$99

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/26

Showing 1-10 of 20 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 September.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 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

How far ahead should I book a flight from Hartford to Chicago Midway Airport?

Use this chart to determine the optimal time to book a round-trip flight from Hartford to Midway. Price data was last updated on September 26, 2025.

To ensure you get the cheapest price possible for a flight from Hartford to Chicago Midway Airport, you should look to book at least 7 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, April is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $160). Flying from Hartford to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 September 29, 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 9% 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 September 28, 2025.

Travelers seeking maximum savings on their Hartford to Chicago Midway Airport flight should consider departing on Saturday at noon when fares are most often at their lowest. Tuesday evenings 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 September 29, 2025.
Read through reviews of airlines operating flights from Hartford to Chicago Midway Airport, such as Southwest, Delta, 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
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
Delta
8.0
Very good
7,964 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
8,924 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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
Frontier
5.8
Fair
3,158 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

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. 4 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 1 outbound flight 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 25m. Delta provides one of the quickest options available for as low as $208. The distance between Hartford and Chicago Midway Airport is about 773 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Frontier is currently your cheapest option to Chicago Midway Airport, with prices starting at $108. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $176 and $177, respectively. Frontier is currently priced 70% 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 $108. On average you can expect to pay $333. 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, April is the cheapest month in which you can book a flight from Hartford to Chicago Midway Airport (average of $160). Flying from Hartford to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 4 airlines flying from Hartford to Midway

Discover the top 4 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$156FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$287FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$177Average$378FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$299Average$471FlexibilityNo cancel feeOn-time69%

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