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$55+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Feb 8 — Feb 151
Sat 2/8
Sat 2/15
1 adult, Economy
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The best prices from Hartford Bradley Intl to Chicago Midway are usually found in September or April, booked 79 days in advance, depart on a Thursday or Monday and return on a Wednesday

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 February 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$277
(Southwest)

One-way from

$55
(Frontier)

Popular in

May

Cheapest in

September

Average price

$334
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. 6% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 3, 2025.

This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/245:40 amBDL - MDW
1 stop4h 00mDelta
Mon 4/285:59 pmMDW - BDL
1 stop4h 11mDelta
Deal found 2/3$277
This Southwest deal was found by Cheapflights users on 2/2. 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 3/43:35 pmBDL - MDW
1 stop6h 50mSouthwest
Tue 3/114:05 pmMDW - BDL
2 stops5h 40mSouthwest
Deal found 2/2$282
This Booking.com deal was found by Cheapflights users on 2/2. 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 4/113:10 pmBDL - MDW
1 stop9h 40mFrontier
Mon 4/141:23 pmMDW - BDL
1 stop21h 16mFrontier
Deal found 2/2$310

Find flights from Hartford to Midway within your budget

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 February 3, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 4/24

5:30 am-6:55 am

Nonstop2h 25m

Chicago Midway

Sat 5/3

1:55 pm-5:00 pm

Nonstop2h 05m

$277

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/25

4:59 pm-10:26 pm

1 stop6h 27m

Chicago Midway

Mon 4/28

5:59 pm-11:10 pm

1 stop4h 11m

$297

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 4/11

3:10 pm-11:50 pm

1 stop9h 40m

Chicago Midway

Mon 4/14

1:23 pm-11:39 am

1 stop21h 16m

$310

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Mon 3/10

4:24 pm-11:58 pm

1 stop8h 34m

$55

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Wed 3/5

6:00 am-7:45 am

Nonstop2h 45m

$129

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 3/4

6:00 am-12:42 pm

1 stop7h 42m

$139

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Thu 3/13

6:30 am-5:36 pm

2 stops12h 06m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust 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.

Travel insights for flights from Hartford to Midway

Get recent, data-driven insights about flights from Hartford to Midway including ideal travel times, pricing trends, and more.

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 January 31, 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 79 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 February 3, 2025.

A simple way to save on the total cost of your ticket is to fly from Hartford to Chicago Midway Airport at noon. 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 afternoon.

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 February 3, 2025.
To help decide which airline to fly from Hartford to Chicago, see what other customers have to say about Southwest, Delta and Frontier. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,570 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,570 reviews
Southwest
8.1
Very good
4,570 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,427 reviews
Southwest
8.1
Very good
4,570 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Frontier
6.0
Okay
3,418 reviews
Southwest
8.1
Very good
4,570 reviews

Crew

8.7

Overall

8.1

Comfort

8.1

Boarding

8.2

Food

7.1

Entertainment

7.7

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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. 3 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.

  • 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 $277. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $297 and $310, respectively. Southwest is currently priced 21% below the average price you’ll pay for this route.

  • What are the cheapest airlines to fly from Hartford to Chicago Midway Airport one-way?

    One-way options have recently been found by users for as low as $55 on Frontier. Other airlines that offer cheap prices include Southwest from $129 and Delta from $139 one-way.

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

    The cheapest flight price from Hartford to Chicago Midway Airport is $150. On average you can expect to pay $349. The most popular route, (Hartford Bradley Intl - Chicago Midway), can usually be booked for $190.

  • 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 Hartford?

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Top 3 airlines flying from Hartford to Midway

Discover the top 3 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 February 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$153Average$257FlexibilityNo cancel feeOn-time62%
DeltaCheapest$176Average$360FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$368FlexibilityNo cancel feeOn-time63%
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