£108 Cheap Flights from Hartford (BDL) to Chicago (MDW)

View £108 flight on Sun, 31 Aug 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 (BDL) to Chicago (MDW)

Prices were available within the past 7 days and start at £108 for one-way flights and for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

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

November is typically the cheapest month to fly

From £95 - £485 per traveller.

Graph displaying average flight prices per month

Flight from Hartford to Chicago route information
Origin airport
Bradley Intl.
Destination airport
Midway Intl.
Distance
1238 km
Average flight time
1 hour 20 mins

Compare flights from Hartford to Chicago easily and book with confidence

For travelling on business or for pleasure, Expedia makes it easy to book your flights from Hartford to Chicago. Operating between them 2 flights per day, 6 airlines cover the route. And Southwest Airlines fly direct, getting you to Midway Intl. in just 0hours. If you have a preferred carrier, use our advanced search tool to find the right flight from Bradley Intl. to Midway Intl..  

To make things even better, in the advanced search, you can also choose to fly economy, premium economy, business or first class, select your maximum number of stops, and pick your preferred departure and arrival time. You can also opt for refundable and direct flights. 

Grab a great deal on your flight from Bradley Intl. (BDL) to Midway Intl. (MDW)

The easiest way to view the best deals on flights from Hartford to Chicago today is to enter your travel dates and hit search. From here, you can sort your results by price to see the cheapest flights first. Right now, return flights from Bradley Intl. to Midway Intl. start at just and range up to .  

To find an even better deal, try  

  • being flexible on your dates – midweek flights can be cheaper
  • looking for other airports near Hartford and Chicago
  • booking your flight during , the cheapest month on this route
  • varying your flight times – early morning and late at night are sometimes cheaper 

Why you should book your Hartford to Chicago flight with Expedia!

We cater for all flight types, cabin classes and airlines. So whether you’re booking flights from Bradley Intl. to Midway Intl. for a budget break or a business trip with a bit of pleasure thrown in, we make it easy to secure the seat that’s right for you.  

Thanks to our supersized inventory that offers great choice all in one place, you know you’ll get a great deal with Expedia. Especially if you bundle your flight together with your hotel, you will unlock amazing savings. For added peace of mind, you can choose flexible bookings or filter to find refundable options, so you won’t pay a fee to change your flight.  

Frequently asked questions

How much is a flight from BDL to Midway Intl. Airport (MDW)?
Based on fares quoted within the last 7 days on Expedia for flights departing within the next year, round-trip flights from Bradley Intl. Airport (BDL) to MDW start from . Make your booking ASAP to secure the best price for your trip. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from Bradley Intl. Airport (BDL) to MDW?
When it comes to cancellation fees, each airline has a different set of terms and conditions. If you decide to cancel your escape, visit our Customer Service Portal.
How do I find cheap flights from BDL to Midway Intl. Airport (MDW) that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for Bradley Intl. Airport (BDL) to Midway Airport flights, you'll see a "no change fees" filter for you to select.
How far is the flight from Bradley Intl. Airport (BDL) to Midway Intl. Airport (MDW)?
It's just 1,250 kilometres between Windsor Locks and Chicago. It's quite possible that you'll spend more time travelling to and from the airport than you will actually flying!
Which airlines fly direct from Bradley International Airport to Midway Intl. Airport (MDW)?
Offering 60 flights every month, Southwest Airlines (WN) is a great choice when flying straight from Bradley Intl. Airport (BDL) to MDW.
Are BDL to MDW flight tickets cheaper when they're purchased at the last minute?
Flight prices are always on the move, so it's no sure thing. While last-minute flight deals between BDL and Midway Airport are of course possible, it's also a good idea to keep a close eye on prices well before you fly. In fact, some carriers publicize their prices up to 12 months ahead of the departure date. Expedia is constantly updating the biggest bargains around, so keep checking back and be ready to grab your seat when the price dips.

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