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$109+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago Midway are usually found in September or November, booked 82 days in advance, depart on a Tuesday or Wednesday 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 June 12, 2025.

Round-trip from

$230
(Southwest)

One-way from

$109
(Delta)

Popular in

March

Cheapest in

September

Average price

$369
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 ($43 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 June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 11/89:45 amBDL - MDW
2 stops10h 00mSouthwest
Mon 11/1011:55 amMDW - BDL
Nonstop2h 00mSouthwest
Deal found 6/11$230
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 8/315:35 amBDL - MDW
1 stop4h 00mDelta
Wed 9/36:00 amMDW - BDL
1 stop6h 36mDelta
Deal found 6/10$245
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1612:27 pmBDL - MDW
1 stop11h 08mFrontier
Mon 8/188:35 amMDW - BDL
1 stop10h 18mFrontier
Deal found 6/11$267

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 June 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

Sat 11/8

9:45 am-6:45 pm

2 stops10h 00m

Chicago Midway

Mon 11/10

11:55 am-2:55 pm

Nonstop2h 00m

$230

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 8/31

1:00 pm-6:37 pm

1 stop6h 37m

Chicago Midway

Wed 9/3

10:11 am-5:59 pm

1 stop6h 48m

$245

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 8/16

12:27 pm-10:35 pm

1 stop11h 08m

Chicago Midway

Mon 8/18

8:35 am-7:53 pm

1 stop10h 18m

$267

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Tue 7/15

6:15 am-1:06 pm

1 stop7h 51m

$109

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Fri 8/22

11:44 am-9:54 am

1 stop23h 10m

$112

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sat 8/16

5:00 pm-6:20 pm

Nonstop2h 20m

$116

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

Sun 8/10

11:04 am-12:21 pm

2 stops26h 17m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/9

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 June 9, 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 June 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 9% on your trip compared to booking a flight at noon.

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 June 12, 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
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Frontier
5.9
Fair
3,295 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Comfort

8.0

Food

7.1

Overall

8.0

Entertainment

7.6

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 2 outbound flights 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 $230. Additional round-trip tickets that might be worth considering are offered by Delta and Frontier, with the lowest prices starting at $245 and $267, respectively. Southwest is currently priced 38% 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 $109 on Delta. Other airlines that offer cheap prices include Frontier from $112 and Southwest from $116 one-way.

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

    The cheapest flight price from Hartford to Chicago Midway Airport is $134. On average you can expect to pay $323. 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 Hartford?

Book flights to Hartford if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$108Average$257FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$125Average$471FlexibilityNo cancel feeOn-time69%
DeltaCheapest$176Average$346FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$232Average$379FlexibilityNo cancel feeOn-time63%

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