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

Search over 321,000 hotels worldwide and 400 airlines worldwide.

Secure incredible value with Expedia's Price Guarantee.

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

$336.00

Chicago

$251.03

Cheap BDL to MDW Flights

Question : How long do most people visit Chicago?
Answer : Of course you're not most people, but if you were, you'd stay roughly four days.

Question : About how long is the flight from Hartford to Chicago?
Answer : When flying from BDL to MDW, it will take two hours and 31 minutes on average.

Question : Which airline is struggling to get to Chicago on time?
Answer : If you're flying Flexjet to Chicago from Hartford, you may be tardy as they're delayed 100% of the time. If you’re on Flexjet, be sure to sign up for the delay notifications to stay up to date with your flight’s status.

Question : How does Hartford to Chicago stack up against the rest of the world in overall promptness?
Answer : Using the combined on-time percentage and average delay breakdown, Hartford to Chicago currently has a 3 out of a possible 5 star rating. A 3-star rating means you should feel slightly worried about getting to Chicago on time.

Question : Interested in traveling in the next 30 days and want to get the lowest fare?
Answer : As of Nov 20th, the best day for booking to Chicago (MDW) is Dec 20th. It costs $336, which is 31% below this route's average price.

Question : What is the likelihood your flight will be delayed for this route?
Answer : Flights from BDL to MDW are on time 85% of the time, ranking in the 69th percentile worldwide. When there is a delay, it averages less than half an hour.

Question : On a daily basis, how many different flight times are available from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)?
Answer : Each day is different, but on average, you can expect to see eight available departure times. You won't have as many options on this route as most other routes departing the United States.

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 Expedia.com, 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.