$118 Find Cheap Flights from Chicago Midway Airport to Boston - Compare and Save

Among airlines operating Chicago Midway Airport to Boston flights:

• Southwest: offers free seat selection

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

Only Southwest operates flights between Chicago Midway Airport and Boston.

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

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 Chicago Midway Airport to Boston.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $167 round-trip via Philadelphia (PHL), compared to $254 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 737-800 family is used most often on this route, operated mainly by American Airlines and Delta. Other aircraft seen on the route include Airbus A220-300 variants.

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

• Atlanta Hartsfield-Jackson (ATL) - 43% of one-stop connections
• Baltimore/Washington (BWI) - 29% of one-stop connections
• Philadelphia (PHL) - 14% of one-stop connections
• Lambert-St Louis (STL) - 14% of one-stop connections

Atlanta Hartsfield-Jackson (ATL) handles the largest share of one-stop connections on this route.

Yes. Being flexible with your travel dates can save you up to 18% on the Chicago Midway Airport to Boston route. Friday is the cheapest departure day at $236 round-trip on average, while Monday is the most expensive at $287, a difference of $51. KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

A flight is considered delayed when it departs 15 minutes or more after its scheduled time. This is the standard used by the US Department of Transportation and most airline industry reporting. On the Chicago Midway Airport to Boston route, 27% of flights were delayed in the past 3 months, with delays averaging 2 hours 17 minutes.

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

Some of the most popular sights in Boston are Fenway Park, TD Garden and Boston Common. These are among the most viewed places in Boston on KAYAK.

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

• Earliest: departs at 5:00 am and lands at 7:20 am
• Latest: departs at 8:40 pm and lands at 11:00 pm.

The flight takes about 2h 20m.

Last-minute fares on this route - booked within 2 weeks of departure - run 27% above the route average of $257. Book 4 weeks before departure for the lowest fares.

A nonstop flight from Chicago Midway Airport to Boston takes 2h 20m, 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 $220 to $1,358. That means the highest observed fare was about 6x higher than the lowest one.

One-way fares from Chicago Midway Airport to Boston are currently lower than usual. Average one-way flight prices are about $118, which is 34% below the typical average for this route.

Southwest is the only airline operating Chicago Midway Airport to Boston flights. 73% of its flights are on time.

Night flights have the fewest delays on this route. Delays tend to pile up throughout the day as one late flight pushes the next, so earlier departures are usually more reliable.

Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 51m, compared with 5h 21m via Baltimore/Washington (BWI) and 9h 15m via Atlanta Hartsfield-Jackson (ATL).

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

Boston Logan Intl Airport (BOS) hosts 5 major car rental companies, with daily rates starting from around $23 for economy cars. Top options include:
• Dollar
• Hertz
• Budget
• Thrifty
• Sixt

Round-trip flights from Chicago Midway Airport to Boston range from $189 to $342, with an average of $257 over the past 12 months. Anything below $189 counts as a good deal.

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