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Flights from Boston to Chicago – Direct & connecting routes

Non-stop airlines Connecting flights Show map Price search

BOS to MDW flights and routes map BOS to MDW – All flight route options from Boston Logan International Airport, Massachusetts, USA to Chicago Midway International, Illinois, USA. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 7 different transit flights. The shortest flight time is 2 hours and 45 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA BOS Boston Logan Airport Boston, MA, USA
USA MDW Chicago Midway , IL, USA
BOS
Boston Logan Airport
USABoston, MA, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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7 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 4-6 flights per day.

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2h 45m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 45m
4-6 flights per day.
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1 stop route options with the same airline:

Duration

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

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4h 22m

Via Detroit DTW
1 stop with Delta Air Lines.
4h 22m
2 flights per day.
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Via Philadelphia PHL
1 stop with Frontier Airlines. 0-1 flights per day.
Begins in 21/8

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4h 49m

Begins in 21/8
Via Philadelphia PHL
1 stop with Frontier Airlines.
4h 49m
0-1 flights per day.
Begins in 21/8
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Via Saint Louis STL
1 stop with Southwest Airlines. 1-2 flights per day.

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5h 35m

Via Saint Louis STL
1 stop with Southwest Airlines.
5h 35m
1-2 flights per day.
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Via Nashville BNA
1 stop with Southwest Airlines. 1-3 flights per day.

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6h 00m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 00m
1-3 flights per day.
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Via Baltimore BWI
1 stop with Southwest Airlines. 3-5 flights per day.

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6h 15m

Via Baltimore BWI
1 stop with Southwest Airlines.
6h 15m
3-5 flights per day.
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Via Minneapolis MSP
1 stop with Delta Air Lines. 2-3 flights per day.

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6h 51m

Via Minneapolis MSP
1 stop with Delta Air Lines.
6h 51m
2-3 flights per day.
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Via Charlotte CLT
1 stop with Southwest Airlines.
Begins in 7/10

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8h 15m

Begins in 7/10
Via Charlotte CLT
1 stop with Southwest Airlines.
8h 15m
Begins in 7/10
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Boston to Chicago flights

With over 137 flights every week and 8 different airlines you have a wide range of options. 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, Philadelphia or any other of the 7 alternatives with connectiing airports.

Boston to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 5:00 am to 9:00 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 29 minutes faster. Delta Air Lines is a member of SkyTeam.

Distance & flight times: Logan Airport to Midway International Airport

The shortest flight time between BOS and MDW is 2 hours and 45 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 45m-863 miles (1389 km)
DTW Detroit4h 22m43m862 miles (1387 km)
PHL Philadelphia4h 49m41m951 miles (1530 km)
STL Saint Louis5h 35m2h 40m1301 miles (2093 km)
BNA Nashville6h 0m2h 50m1343 miles (2161 km)
BWI Baltimore6h 15m2h 30m983 miles (1582 km)
MSP Minneapolis6h 51m57m1477 miles (2376 km)
CLT Charlotte8h 15m2h 25m1317 miles (2119 km)
The flight times and layover times in the table above are approximate and may 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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Boston - Chicago route map and flight paths
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You can fly non-stop from Boston (BOS) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 2 hours and 45 minutes. If you travel with a connecting flight instead, for example via Detroit, the total flight time will be 4 hours and 22 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Delta Air Lines, Frontier Airlines or Southwest Airlines is also an option.

The flight time between Boston Logan Airport (BOS) and Chicago Midway International (MDW) is approximately 2 hours and 45 minutes. The distance between the two airports 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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