Beginning of main content
Round Trip Icon
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap BDL to MDW Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Hartford to Chicago route information

Origin Airport Bradley Intl.
Destination Airport Midway Intl.
Airlines Serving Delta
Flight Price $358
Distance 773 mi



New Haven




Cheap BDL to MDW Flights

  • What is the cheapest day to fly to Chicago?

    If you are wanting to save some money, look at Dec 4th. As of Nov 11th, it's showing the cheapest ticket at $349. That is 31% below the average for this route, so you can spend that extra cash on an adventure in Chicago.
  • How much is a plane ticket to Chicago (MDW) from Hartford (BDL)?

    Cost can range from $349 to $807, prices for BDL to MDW fluctuate less than most routes in the United States. However, usually the sooner you book, the more you'll be able to save.
  • What is the cheapest day to fly?

    The cheapest day to fly from Hartford to Chicago is on Thursday. If you would like to save a bit of cash on your next flight look for flights on Thursday.
  • Is there an alternative airport near Chicago?

    There is another airport outside Chicago. O'Hare International Airport (ORD) is 16 miles away, and over the next two months flights are being booked 22% cheaper than flights to Chicago Midway International Airport.
  • Can I change the date of my flight?

    Yes, you can change your departure date. If you wish to save some funds in doing so, the lowest-cost day to fly in November is Thursday. Being flexible with your travel days can provide you extra savings when booking.
  • Do some days of the week have more flight times than others?

    With 11 total flight time options, Sunday provides the most flexibility from BDL to MDW. Thursday currently offers the fewest number of flight times with only four options.
  • How long is the flight from BDL to MDW?

    If you're able to take the direct flight (which is offered by Southwest Airlines), you will be able to leave BDL at 5:50 AM EST and get to MDW at 7:15 AM CST (two hours and 25 minutes). Remember, there is a one-hour time difference.

Hartford to Chicago Flights

Sometimes you just need to get out of town or maybe you’re looking for a change of scenery. Regardless of the reason, a flight from Hartford to Chicago will do just the trick! Go on, plan to see all the famous landmarks and eat your weight in the local cuisine. Your trip is beckoning, so answer the call by packing your suitcase and filling your travel itinerary with exploring Chicago.

Whether you’re flying for business or jet-setting on your personal time, you’ve come to the right place. Here at, we’ll pair you up with BDL to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Hartford for new horizons? Browse through our cheap airfare, and filter by flight times and dates until you find just what you had in mind. From flights without layovers to ones that arrive early in the morning, you’ll come across plane tickets that suit your travel preferences. You can even bundle your flight to MDW with hotels and car rentals to score even bigger savings.

All set to hit the clouds? Book your travel arrangements with us today and have left-over money to put toward your travel outings and adventures.

Package Disclaimer

*Savings amount equal to 100% when flight + hotel are booked together. Prices based on searches conducted by fellow shoppers within the past 24 hours. There is no guarantee that these prices will be in effect at the time of your search. Vacation package savings are based on comparison to prices on of the same components booked separately. Savings vary based on origin/destination, length of trip, stay dates and travel partners, and aren't available on all packages.