$61 Cheap Flights from Hartford (BDL) to Chicago (MDW)

View $61 flight on Thu, Feb 19, 2026Opens 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 $61 for one-way flights and $157 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Feb 6 - Mon, Feb 9
BDL
Hartford
MDW
Chicago
$157 Roundtrip, found 4 hours ago
$157
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Feb 6 from Hartford to Chicago, returning Mon, Feb 9, priced at $157 found 4 hours ago
Southwest Airlines
Tue, Dec 16 - Thu, Dec 25
BDL
Hartford
MDW
Chicago
$162 Roundtrip, found 4 days ago
$162
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Tue, Dec 16 from Hartford to Chicago, returning Thu, Dec 25, priced at $162 found 4 days ago
Southwest Airlines
Fri, Feb 6 - Mon, Feb 9
BDL
Hartford
MDW
Chicago
$167 Roundtrip, found 4 hours ago
$167
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Fri, Feb 6 from Hartford to Chicago, returning Mon, Feb 9, priced at $167 found 4 hours ago
Delta
Tue, Dec 16 - Thu, Dec 25
BDL
Hartford
MDW
Chicago
$172 Roundtrip, found 4 days ago
$172
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Dec 16 from Hartford to Chicago, returning Thu, Dec 25, priced at $172 found 4 days ago
Delta
Wed, Dec 31 - Thu, Jan 1
BDL
Hartford
MDW
Chicago
$177 Roundtrip, found 3 hours ago
$177
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Dec 31 from Hartford to Chicago, returning Thu, Jan 1, priced at $177 found 3 hours ago
Southwest Airlines
Fri, Feb 20 - Tue, Feb 24
BDL
Hartford
MDW
Chicago
$178 Roundtrip, found 3 days ago
$178
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Feb 20 from Hartford to Chicago, returning Tue, Feb 24, priced at $178 found 3 days ago
Southwest Airlines
Sun, Dec 7 - Thu, Dec 11
BDL
Hartford
MDW
Chicago
$182 Roundtrip, found 4 hours ago
$182
Roundtrip
found 4 hours ago
Select Southwest Airlines flight, departing Sun, Dec 7 from Hartford to Chicago, returning Thu, Dec 11, priced at $182 found 4 hours ago
Frontier Airlines
Thu, Nov 20 - Thu, Dec 4
BDL
Hartford
MDW
Chicago
$199 Roundtrip, found 3 days ago
$199
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Nov 20 from Hartford to Chicago, returning Thu, Dec 4, priced at $199 found 3 days ago
Frontier Airlines
Sat, Nov 15 - Mon, Nov 24
BDL
Hartford
MDW
Chicago
$200 Roundtrip, found 3 days ago
$200
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Hartford to Chicago, returning Mon, Nov 24, priced at $200 found 3 days ago
Delta
Fri, Feb 6 - Mon, Feb 9
BDL
Hartford
MDW
Chicago
$202 Roundtrip, found 4 hours ago
$202
Roundtrip
found 4 hours ago
Select Delta flight, departing Fri, Feb 6 from Hartford to Chicago, returning Mon, Feb 9, priced at $202 found 4 hours ago

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

September is typically the cheapest month to fly

From $131 - $667 per traveler.

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 $212
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $212

Frequently asked questions

How much does a flight from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) cost?
Snag a cheap one-way flight from $61 or cheap return flight from $157 from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight offers on this route.
What is the cheapest month to fly from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
Planning your getaway for February is a great way to save, as it's the cheapest month for flights between BDL and MDW. You'll typically find the lowest fares during the off-season.
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 Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare airlines and find the most affordable carrier that'll take you from BDL to MDW. Then, sort your results by "Price (lowest to highest)" to snap up the best deal available.
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.

Travel information

Origin airport
Bradley Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$157
Distance
773 mi
Average flight time
1 hour 30 mins

Book with confidence

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 February. 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 $61 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.

 

Hartford to Chicago Flights

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