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Cheap BOS to MDW Flights

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

Providence

$192.00

Chicago

$112.60

Cheap BOS to MDW Flights

Question : Which airline is offering the cheapest flight from BOS to MDW?
Answer : Delta Air Lines is the leader in keeping costs down for their passengers over the next three months. Bookings are being made at just $142 and, when compared to the high-end bookings of $909, it's quite a deal.

Question : What day has the most flight time options?
Answer : The day with the most departure times for this route is Sunday with 14 options. However, with only seven flight times, Thursday doesn't offer quite as many options when finding that perfect departure time.

Question : Looking for the fastest flight from BOS to MDW?
Answer : Southwest Airlines can get you there in two hours and 45 minutes. For example, if you were to leave Boston at 3:30 PM EST, you would arrive in Chicago at 5:15 PM CST (remember, there is a one-hour time change).

Question : If your plans are flexible, have you considered changing your departure day?
Answer : Tuesday is your lowest-cost day to fly in January. Having flexibility in your travel plans means you can save more, so be sure to plan ahead when possible.

Question : If punctuality is required for you to book a flight, which airline is your best bet?
Answer : Southwest Airlines leads the way with a 77% on-time rate. Stick to Southwest Airlines and you won't spend more time in airports than you have to. If they are delayed for some reason though, the average delay is 23 minutes.

Question : What price range should you expect when booking from Boston (BOS) to Chicago (MDW)?
Answer : Ranging from $142 to $909, prices for BOS to MDW do fluctuate more than the majority of routes in the United States. The further out you book a route, the more likely you are to save.

Question : How many days should you spend in Chicago?
Answer : Passengers from BOS to MDW stay four days on average.

Boston 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 Boston 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 BOS to MDW flights that won’t make your bank account wince. Ready to temporarily leave behind Boston 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.