$104 Cheap Flights from Hartford (BDL) to Chicago (MDW)

View $104 flight on Sat, May 24, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Hartford to Chicago (BDL-MDW)

Prices were available within the past 7 days and start at $104 for one-way flights and $188 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 24 - Sat, May 31
BDL
Hartford
MDW
Chicago
$188 Roundtrip, found 17 hours ago
$188
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Hartford to Chicago, returning Sat, May 31, priced at $188 found 17 hours ago
Frontier Airlines
Sat, May 31 - Sun, Jun 1
BDL
Hartford
MDW
Chicago
$198 Roundtrip, found 14 hours ago
$198
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Hartford to Chicago, returning Sun, Jun 1, priced at $198 found 14 hours ago
Frontier Airlines
Sat, May 31 - Thu, Jun 5
BDL
Hartford
MDW
Chicago
$218 Roundtrip, found 5 hours ago
$218
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Hartford to Chicago, returning Thu, Jun 5, priced at $218 found 5 hours ago
Frontier Airlines
Sat, May 31 - Sat, Jun 14
BDL
Hartford
MDW
Chicago
$221 Roundtrip, found 14 hours ago
$221
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Hartford to Chicago, returning Sat, Jun 14, priced at $221 found 14 hours ago
Southwest Airlines
Thu, May 29 - Sat, May 31
BDL
Hartford
MDW
Chicago
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Thu, May 29 from Hartford to Chicago, returning Sat, May 31, priced at $228 found 5 hours ago
Frontier Airlines
Sat, May 31 - Sat, Jun 7
BDL
Hartford
MDW
Chicago
$228 Roundtrip, found 5 hours ago
$228
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Hartford to Chicago, returning Sat, Jun 7, priced at $228 found 5 hours ago
Frontier Airlines
Sat, May 24 - Sat, May 31
BDL
Hartford
MDW
Chicago
$231 Roundtrip, found 17 hours ago
$231
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Hartford to Chicago, returning Sat, May 31, priced at $231 found 17 hours ago
Frontier Airlines
Thu, May 29 - Sat, Jun 14
BDL
Hartford
MDW
Chicago
$231 Roundtrip, found 14 hours ago
$231
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, May 29 from Hartford to Chicago, returning Sat, Jun 14, priced at $231 found 14 hours ago
Frontier Airlines
Sat, May 24 - Tue, May 27
BDL
Hartford
MDW
Chicago
$236 Roundtrip, found 17 hours ago
$236
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, May 24 from Hartford to Chicago, returning Tue, May 27, priced at $236 found 17 hours ago
Delta
Sat, Jul 26 - Sat, Aug 2
BDL
Hartford
MDW
Chicago
$293 Roundtrip, found 4 hours ago
$293
Roundtrip
found 4 hours ago
Select Delta flight, departing Sat, Jul 26 from Hartford to Chicago, returning Sat, Aug 2, priced at $293 found 4 hours ago

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 $273. 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 May 21 2025 and touching down at MDW. The price was last updated on April 24 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 $137 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 July 5 2025. Prices were last updated on April 24 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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