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

    Plan, book, fly with confidence
  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 30% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in
Hartford to Chicago route information
Origin airport
Bradley Intl.
Destination airport
Midway Intl.
Distance
1238 km

Perfect flights from Hartford to Chicago

Your Journey from Hartford to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Hartford to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including . Our selection of flights from Bradley Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from airlines, you're bound to find the perfect flight.
 

Maximizing Value with Hartford to Chicago Flights

Experience the joy of finding cheap flights from Bradley Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares and roundtrip prices *.
 

Pre-Flight Essentials

Ensure a smooth journey from Hartford to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of Chicago. From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Hartford to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Hartford to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Hartford to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Hartford to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

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.
*Available to Expedia members.