HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$82+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — MDW
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Hartford to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Hartford Bradley Intl to Chicago Midway are usually found in September or August, booked 72 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 agosto 14, 2025.

Round-trip from

$177
(Southwest)

One-way from

$82
(Frontier)

Popular in

March

Cheapest in

September

Average price

$331
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. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

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 agosto 14, 2025.

This Southwest deal was found by Cheapflights users on 8/12. 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.
jue. 9/115:30 amBDL - MDW
Nonstop2h 20mSouthwest
jue. 9/189:45 amMDW - BDL
Nonstop2h 05mSouthwest
Deal found 8/12$177
This FlightHub deal was found by Cheapflights users on 8/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/268:52 pmBDL - MDW
1 stop13h 59mFrontier
dom. 9/2810:13 amMDW - BDL
1 stop8h 29mFrontier
Deal found 8/14$185
This Southwest deal was found by Cheapflights users on 8/14. 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.
mar. 9/95:20 pmBDL - MDW
Nonstop2h 20mSouthwest
mié. 9/106:10 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 8/14$187
This Frontier deal was found by Cheapflights users on 8/13. 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.
jue. 9/410:30 amBDL - MDW
1 stop6h 28mFrontier
lun. 9/88:15 amMDW - BDL
2 stops10h 42mFrontier
Deal found 8/13$190
This Southwest deal was found by Cheapflights users on 8/14. 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.
jue. 9/412:40 pmBDL - MDW
Nonstop2h 20mSouthwest
dom. 9/710:00 amMDW - BDL
Nonstop2h 10mSouthwest
Deal found 8/14$192
This Frontier deal was found by Cheapflights users on 8/14. 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.
jue. 9/1810:30 amBDL - MDW
1 stop6h 28mFrontier
dom. 9/216:30 amMDW - BDL
2 stops12h 22mFrontier
Deal found 8/14$193
This Priceline deal was found by Cheapflights users on 8/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/410:30 amBDL - MDW
1 stop6h 28mFrontier
dom. 9/710:13 amMDW - BDL
1 stop8h 39mFrontier
Deal found 8/14$194
This Frontier deal was found by Cheapflights users on 8/14. 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.
jue. 9/1110:30 amBDL - MDW
1 stop6h 28mFrontier
vie. 9/127:15 amMDW - BDL
2 stops11h 29mFrontier
Deal found 8/14$195
This Southwest deal was found by Cheapflights users on 8/13. 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.
vie. 9/125:30 amBDL - MDW
Nonstop2h 20mSouthwest
mar. 9/166:10 pmMDW - BDL
Nonstop2h 10mSouthwest
Deal found 8/13$199
This Southwest deal was found by Cheapflights users on 8/14. 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.
mié. 9/105:20 pmBDL - MDW
Nonstop2h 20mSouthwest
sáb. 9/1312:55 pmMDW - BDL
Nonstop2h 05mSouthwest
Deal found 8/14$203

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 agosto 14, 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

mar. 10/28

12:55 pm-2:20 pm

Nonstop2h 25m

Chicago Midway

lun. 11/3

6:15 pm-9:25 pm

Nonstop2h 10m

$177

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 9/18

5:30 am-6:50 am

Nonstop2h 20m

Chicago Midway

jue. 9/18

9:45 am-12:50 pm

Nonstop2h 05m

$177

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 10/2

5:25 am-6:50 am

Nonstop2h 25m

Chicago Midway

lun. 10/6

9:30 am-12:35 pm

Nonstop2h 05m

$177

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 9/11

5:30 am-6:50 am

Nonstop2h 20m

Chicago Midway

jue. 9/18

9:45 am-12:50 pm

Nonstop2h 05m

$177

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

vie. 9/26

8:52 pm-9:51 am

1 stop13h 59m

Chicago Midway

dom. 9/28

10:13 am-7:42 pm

1 stop8h 29m

$185

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 12/4

3:40 pm-9:05 pm

1 stop6h 25m

Chicago Midway

dom. 12/7

11:55 am-2:55 pm

Nonstop2h 00m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mié. 10/29

6:00 am-12:00 pm

1 stop7h 00m

Chicago Midway

mar. 11/4

1:45 pm-4:45 pm

Nonstop2h 00m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

dom. 9/14

5:35 am-6:55 am

Nonstop2h 20m

Chicago Midway

mar. 9/16

7:25 am-1:10 pm

1 stop4h 45m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

mar. 9/9

5:20 pm-6:40 pm

Nonstop2h 20m

Chicago Midway

mié. 9/10

6:10 pm-9:20 pm

Nonstop2h 10m

$187

HartfordChicago

BDL - MDW

BDLMDW

Hartford Bradley Intl

jue. 9/4

10:30 am-3:58 pm

1 stop6h 28m

Chicago Midway

lun. 9/8

8:15 am-7:57 pm

2 stops10h 42m

$190

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 20 results
1
2

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 August 8, 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 72 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 agosto 14, 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 10% 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 August 10, 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 agosto 14, 2025.
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
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.5

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 1 outbound flight to Chicago Midway per day.

  • 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 $177. Southwest is currently priced 52% 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 $63. On average you can expect to pay $285. The most popular route, (Hartford Bradley Intl - Chicago Midway), can usually be booked for $137.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$177Average$364FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.