$117 Find Cheap Flights from Boston to Chicago Midway Airport - Compare and Save

Among airlines operating Boston to Chicago Midway Airport flights:

• Southwest: offers free seat selection

Extra legroom and free seat selection availability depends on fare class and route.

Only Southwest operates flights between Boston and Chicago Midway Airport.

Flights from Boston to Chicago Midway Airport usually depart from Boston Logan Intl (BOS) and arrive at Chicago Midway (MDW).

Here are some options for this route, based on selected ticket types and cabin classes:

• Southwest: a cabin bag and a checked bag in Economy Class
• JetBlue: a cabin bag in Economy Class class

Bag allowance can vary by ticket type, cabin class, route and airline, so travelers should check the fare details before booking.

Only Economy Class is available on flights from Boston to Chicago Midway Airport.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $157 round-trip via Orlando (MCO), compared to $253 for nonstop.

There is no standard. Checked-bag policies vary by airline on this route. Most carriers charge $45–$90 for the first checked bag in economy. Premium fares and elite-status bookings typically include a free checked bag.

The Boeing 737 MAX 8 family is used most often on this route, operated mainly by Southwest and United Airlines. Other aircraft seen on the route include Boeing 737-800 variants.

One-stop flights from Boston to Chicago Midway Airport most commonly connect through:

• Detroit Metropolitan Wayne County (DTW) - 36% of one-stop connections
• Lambert-St Louis (STL) - 24% of one-stop connections
• Atlanta Hartsfield-Jackson (ATL) - 16% of one-stop connections
• Orlando (MCO) - 16% of one-stop connections

Detroit Metropolitan Wayne County (DTW) handles the largest share of one-stop connections on this route.

On the Boston to Chicago Midway Airport route, being flexible with your departure day can save you up to 32%. Saturday is the cheapest day at $199 round-trip on average, while Sunday is the most expensive at $289: a $90 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

Afternoon is the busiest departure period on Boston to Chicago Midway Airport flights, with 50% of flights leaving in that window. Morning departures account for 25%, evening flights for 25%, and night flights for 0%.

Some of the most popular sights in Chicago Midway Airport are Magnificent Mile, Grant Park and River North. These are among the most viewed places in Chicago Midway Airport on KAYAK.

These are the earliest and latest flight times available from Boston to Chicago Midway Airport:

• Earliest: departs at 5:50 am and lands at 8:29 am
• Latest: departs at 10:50 pm and lands at 1:29 am.

The flight takes about 2h 39m.

Last-minute fares on this route - booked within 2 weeks of departure - run 24% above the route average of $251. Book 7 weeks before departure for the lowest fares.

A nonstop flight from Boston to Chicago Midway Airport takes 2h 39m, covering 857 miles.

No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID, or another TSA-accepted form of identification.

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $216 to $1,273. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Boston to Chicago Midway Airport are currently lower than usual. Average one-way flight prices are about $118, which is 33% below the typical average for this route.

Flying via Detroit Metropolitan Wayne County (DTW) gives the shortest average 1-stop total travel time at 4h 15m, compared with 5h 27m via Baltimore/Washington (BWI) and 5h 55m via Lambert-St Louis (STL).

Chicago Midway Airport is 1 hour behind Boston (Central Time vs Eastern Time). Plan for the time shift when scheduling connections or first-day activities.

Chicago Midway Airport (MDW) hosts 5 major car rental companies, with daily rates starting from around $32 for economy cars. Top options include:
• Hertz
• Dollar
• Budget
• Alamo
• Rent-A-Wreck

Round-trip flights from Boston to Chicago Midway Airport range from $185 to $342, with an average of $251 over the past 12 months. Anything below $185 counts as a good deal.

JetBlue is the only airline on the Boston to Chicago Midway Airport route offering in-flight Wi-Fi. Pricing depends on fare class.