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Flights from Boston to Chicago

BOS to MDW flights and routes map BOS to MDW. All flight routes from General Edward Lawrence Logan International, Massachusetts, USA to Chicago Midway International, Illinois, USA. These flights are operated by 3 different airlines. You can either fly non-stop with Southwest Airlines or choose from 6 different transit flights. The shortest flight time is 2 hours and 40 minutes.

From
To
USA BOS General Edward Lawrence Logan Boston, MA, USA
USA MDW Chicago Midway , IL, USA
BOS
General Edward Lawrence Logan
USABoston, MA, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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6 routes with 1 stop found »
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Non-stop routes:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 3-4 flights per day.

SCHEDULE
2h 40m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 40m
3-4 flights per day.
SCHEDULE
Usually in time
Some delays
Usually delayed
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1 stop routes with the same airline:

Duration

Via Detroit DTW
1 stop with Delta Air Lines. 2-3 flights per day.

SCHEDULE
4h 29m

Via Detroit DTW
1 stop with Delta Air Lines.
4h 29m
2-3 flights per day.
SCHEDULE
Via Saint Louis STL
1 stop with Southwest Airlines. 1-3 flights per day.

SCHEDULE
5h 30m

Via Saint Louis STL
1 stop with Southwest Airlines.
5h 30m
1-3 flights per day.
SCHEDULE
Via Nashville BNA
1 stop with Southwest Airlines. 1-2 flights per day.

SCHEDULE
5h 45m

Via Nashville BNA
1 stop with Southwest Airlines.
5h 45m
1-2 flights per day.
SCHEDULE
Via Baltimore BWI
1 stop with Southwest Airlines. 2-7 flights per day.

SCHEDULE
6h 10m

Via Baltimore BWI
1 stop with Southwest Airlines.
6h 10m
2-7 flights per day.
SCHEDULE
Via Minneapolis MSP
1 stop with Delta Air Lines. 2-3 flights per day.

SCHEDULE
6h 35m

Via Minneapolis MSP
1 stop with Delta Air Lines.
6h 35m
2-3 flights per day.
SCHEDULE
Via Philadelphia PHL
1 stop with Frontier Airlines. 0-1 flights per day.
Mon & Wed

SCHEDULE
6h 44m

Mon & Wed
Via Philadelphia PHL
1 stop with Frontier Airlines.
6h 44m
0-1 flights per day.
Mon & Wed
SCHEDULE
Usually in time
Some delays
Usually delayed
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Boston to Chicago flights

With over 143 flights every week and 7 different airlines you have a wide option of flights to choose from. You can fly non-stop to Chicago (MDW) from Boston (BOS) with Southwest Airlines but if a stopover option suits you better you can choose to fly via Detroit, Saint Louis or any other of the 6 alternatives with flight connections.

Boston to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 5 am to 21 pm. You can also catch a transit flight via Saint Louis or Nashville.

With Delta Air Lines

If you choose to fly with Delta Air Lines from Boston to Chicago you can make a transit either via Detroit or via Minneapolis. The route via Detroit is 2 hours and 6 minutes faster. Delta Air Lines is a member of SkyTeam.

With Frontier Airlines

If you fly from Boston with Frontier Airlines you will do a stopover in Philadelphia, PHL before reaching Chicago. This flight trip will take 6 hours and 44 minutes and you can fly every Monday or Wednesday with departures at 07:49, 08:19 or 12:59.

Miles & flight time: BOS - MDW

The shortest flight time between BOS and MDW is 2 hours and 40 minutes.

ViaTotal flight timeLayover timeMiles
Direct2h 40m-863 (1389 km)
DTW Detroit4h 29m1h 32m862 (1387 km)
STL Saint Louis5h 30m1h 5m1301 (2093 km)
BNA Nashville5h 45m50m1343 (2161 km)
BWI Baltimore6h 10m2h 15m983 (1582 km)
MSP Minneapolis6h 35m1h 35m1477 (2376 km)
PHL Philadelphia6h 44m2h 59m951 (1530 km)
The flight times and layover times in the table above are approximate and vary depending on flight number, aircraft, airline, weather and time of day.BOS-MDW flight routesBoston to Chicago flight routes illustrated on a map.
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Unpublished Flight Rates From Boston to Chicago

You can fly to Chicago (MDW) from Boston (BOS) non-stop with Southwest Airlines. The flight takes approximately 2 hours and 40 minutes. If you travel with a connecting flight instead, for example via Detroit, the total flight time will be 4 hours and 29 minutes.

If you are interested in direct flights, you can choose from Southwest Airlines. If you choose to fly with stops instead you can fly with Delta Air Lines, Southwest Airlines or Frontier Airlines.

The flight time between General Edward Lawrence Logan, BOS and Chicago Midway International, MDW, is 2 hours and 40 minutes. The distance is 1477 miles (or 2376 kilometers).

Yes, you can fly non-stop to MDW from BOS with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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