$111 Find Cheap Flights from Chicago Midway Airport to Boston - Compare and Save

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

• Earliest: departs at 5:00 am and lands at 7:19 am
• Latest: departs at 8:40 pm and lands at 10:59 pm.

The flight takes about 2h 19m.

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

A nonstop flight from Chicago Midway Airport to Boston takes 2h 19m, 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.

Round-trip flights from Chicago Midway Airport to Boston range from $204 to $355, with an average of $269 over the past 12 months. Anything below $204 counts as a good deal.

Last-minute fares on this route (booked within two weeks of departure) run 23% above the $269 route average. Book 15 weeks before departure for the lowest fares.

On this route, layover flights are cheaper than nonstop options on average. Layover fares average $167 round-trip via Philadelphia (PHL), compared to $266 for nonstop.

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

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 Airbus A220-300 family is used most often on this route, operated mainly by JetBlue and Delta. Other aircraft seen on the route include Boeing 737 MAX 8 variants.

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

Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $220 to $1,181. That means the highest observed fare was about 5x higher than the lowest one.

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

One-way fares from Chicago Midway Airport to Boston are currently lower than usual. Average one-way flight prices are about $111, which is 37% below the typical average for this route.

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

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

Night flights have the fewest delays on this route, while afternoon departures tend to have the most.

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 2h 19m.

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

• Atlanta Hartsfield-Jackson (ATL) - 50% of one-stop connections
• Baltimore/Washington (BWI) - 17% of one-stop connections
• Philadelphia (PHL) - 17% of one-stop connections
• Lambert-St Louis (STL) - 17% of one-stop connections

Yes. Flexible dates can save you up to 17% on flights from Chicago Midway Airport to Boston. Friday is the cheapest departure day at $256 round-trip on average, while Monday is the most expensive at $305, a difference of $49.

KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

Only Southwest operates flights between Chicago Midway Airport and Boston.

Flying via Lambert-St Louis (STL) gives the shortest average 1-stop total travel time at 4h 51m, compared with 6h 22m 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.

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

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.

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 always check the fare details before booking.