$69 Cheap Flights from Hartford (BDL) to Chicago (MDW)

View $69 flight on Thu, Nov 6, 2025Opens in a new window

Popular airlines from Bradley Intl. Airport (BDL) to Chicago Midway Airport (MDW)

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Cheap Flights from Hartford to Chicago (BDL-MDW)

Prices were available within the past 7 days and start at $69 for one-way flights and $134 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Nov 1 - Tue, Nov 4
BDL
Hartford
MDW
Chicago
$134 Roundtrip, found 6 days ago
$134
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Hartford to Chicago, returning Tue, Nov 4, priced at $134 found 6 days ago
Southwest Airlines
Sat, Nov 1 - Sun, Nov 2
BDL
Hartford
MDW
Chicago
$135 Roundtrip, found 4 days ago
$135
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Hartford to Chicago, returning Sun, Nov 2, priced at $135 found 4 days ago
Southwest Airlines
Thu, Nov 6 - Sun, Nov 9
BDL
Hartford
MDW
Chicago
$137 Roundtrip, just found
$137
Roundtrip
just found
Select Southwest Airlines flight, departing Thu, Nov 6 from Hartford to Chicago, returning Sun, Nov 9, priced at $137 just found
Southwest Airlines
Sat, Aug 30 - Sun, Aug 31
BDL
Hartford
MDW
Chicago
$139 Roundtrip, found 6 days ago
$139
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Sat, Aug 30 from Hartford to Chicago, returning Sun, Aug 31, priced at $139 found 6 days ago
Southwest Airlines
Thu, Sep 25 - Sun, Sep 28
BDL
Hartford
MDW
Chicago
$147 Roundtrip, found 3 hours ago
$147
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 25 from Hartford to Chicago, returning Sun, Sep 28, priced at $147 found 3 hours ago
Southwest Airlines
Thu, Sep 4 - Sun, Sep 7
BDL
Hartford
MDW
Chicago
$152 Roundtrip, found 14 hours ago
$152
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Thu, Sep 4 from Hartford to Chicago, returning Sun, Sep 7, priced at $152 found 14 hours ago
Southwest Airlines
Thu, Aug 28 - Tue, Sep 2
BDL
Hartford
MDW
Chicago
$155 Roundtrip, found 5 days ago
$155
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Aug 28 from Hartford to Chicago, returning Tue, Sep 2, priced at $155 found 5 days ago
Southwest Airlines
Tue, Aug 5 - Thu, Aug 7
BDL
Hartford
MDW
Chicago
$157 Roundtrip, found 13 hours ago
$157
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Tue, Aug 5 from Hartford to Chicago, returning Thu, Aug 7, priced at $157 found 13 hours ago
Delta
Tue, Sep 16 - Sun, Sep 21
BDL
Hartford
MDW
Chicago
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 16 from Hartford to Chicago, returning Sun, Sep 21, priced at $167 found 2 days ago
Frontier Airlines
Thu, Sep 18 - Mon, Sep 22
BDL
Hartford
MDW
Chicago
$260 Roundtrip, found 5 days ago
$260
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Hartford to Chicago, returning Mon, Sep 22, priced at $260 found 5 days ago

Find the cheapest month to fly from Hartford (BDL) to Chicago (MDW)

November is typically the cheapest month to fly

From $128 - $639 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $214
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $214
Flights from Hartford (BDL) to Chicago (MDW)
Origin airport
Bradley Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$133
Distance
773 mi
Average flight time
1 hour 23 mins

Hartford to Chicago Flights

The cheapest times to fly from Hartford to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Hartford to Chicago are during the month of November. You can find some of the cheapest flights from Hartford to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Hartford to Chicago

Sunday is one of the best days to book for cheap flights from Hartford to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Hartford to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Hartford to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $69 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Hartford to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Hartford to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) cost?
Cheap return flights from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) start from $115. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines flight leaving BDL on August 8 2025 and touching down at MDW. The price was last updated on July 13 2025 and has not changed since.
What is the cheapest month to fly from BDL to MDW?
The cheapest flights from BDL to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
You can fly directly from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) on a Southwest Airlines flight.
What is the cheapest airline that flies from BDL to MDW?
With prices starting from $58 for a one-way flight from BDL to MDW, Southwest Airlines is currently the cheapest carrier for this route. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from BDL on September 11 2025. Prices were last updated on July 13 2025 and have not changed since.
How many flights per day from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
On average, only 1 nonstop flight departs each day from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW). Need other options? Use Expedia's filters to discover flights with layovers and explore a new city along the way.
What are the most popular departure times for flights from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
The 6 AM departures from BDL to MDW are the most sought after. Prices can be higher for these popular slots. If you want to save money, choose a less crowded time to fly.
What day of the week has the most flights from BDL to MDW?
If you depart on a Friday, you'll get the biggest range of choices for flights from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW).
What is the earliest flight from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
The first flight of the day departing from Bradley Intl. Airport (BDL) is at around 6:00AM UTC-5. Catch this flight and you'll reach Midway Intl. Airport (MDW) at approximately 7:45AM UTC-6. The entire trip takes 2h 45m.
How long does it take to fly from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
Typically, it takes 2 hours and 41 minutes to fly the 770 mi from BDL to MDW.
What airline has the least delays from BDL to MDW?
Southwest Airlines has the strongest track record for on-time direct flights from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW), with an on-time rating of 87%. Use the Expedia App to check your flight status before you jet off and get immediate updates about any changes.
What is the best time to fly from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
To avoid potential delays on the Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later flights have a 22% higher chance of being canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Bradley Intl. Airport (BDL)?
You can land at O'Hare Intl. Airport (ORD) or Midway Intl. Airport (MDW) when you travel to Chicago on a direct flight from Bradley Intl. Airport (BDL).
Is it cheaper to buy a plane ticket from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from BDL to MDW shortly before your trip is usually more expensive. However, if there's some wiggle room with your schedule, you could snag a cheap last-minute fare.
Is it cheaper to book a BDL to MDW flight and hotel package?
You'll generally save money by securing a BDL to MDW flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's simple to manage everything in one place. After selecting your ideal flights and accommodations, consider adding extras including tours, car rentals and activities.
Can I cancel or change the date of my flight from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
Typically, you can modify or cancel your BDL to MDW flight. However, additional fees may apply, especially if your booking was made over 24 hours ago. Check your itinerary for the airline's guidelines and fees on flight changes, or if you'd like further details, go to our Customer Service portal.

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