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Flights from New York to Chicago – Direct & connecting routes

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LGA to MDW flights and routes map LGA to MDW – All flight route options from La Guardia, New York, USA to Chicago Midway International, Illinois, USA. These flights are operated by 3 airlines. Fly non-stop with Southwest Airlines or choose from 3 different transit flights. The shortest flight time is 2 hours and 30 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 LGA La Guardia New York, NY, USA
USA MDW Chicago Midway , IL, USA
LGA
La Guardia
USANew York, NY, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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4 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 5-7 flights per day.

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2h 30m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 30m
5-7 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. 2-3 flights per day.

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3h 59m

Via Detroit DTW
1 stop with Delta Air Lines.
3h 59m
2-3 flights per day.
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Via Saint Louis STL
1 stop with Southwest Airlines. 0-1 flights per day.

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6h 03m

Via Saint Louis STL
1 stop with Southwest Airlines.
6h 03m
0-1 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 20m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 20m
1-3 flights per day.
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1 stop route options with codeshare or different airlines:

Duration

Via Detroit DTW With American Airlines & Delta Air Lines 0-2 flights per day.

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5h 29m

Via Detroit DTW
5h 29m
With American Airlines & Delta Air Lines 0-2 flights per day.
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New York to Chicago flights

With over 95 flights every week and 4 different airlines you have a wide range of options. You can fly non-stop to Chicago (MDW) from New York (LGA) 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 3 alternatives with connectiing airports.

Tip! You can also fly to Chicago from John F Kennedy International (JFK).

New York to Chicago with Southwest Airlines

You can fly non-stop every weekday with flights departing from 6:00 am to 9:00 pm. You can also take a connecting flight via Saint Louis or Nashville.

With Delta Air Lines

If you fly from New York with Delta Air Lines you will do a stopover in Detroit, DTW before reaching Chicago. This flight trip will take 3 hours and 59 minutes and you can fly every weekday with departures at 6:00 am, 9:00 am or 2:00 pm. Delta Air Lines is a member of SkyTeam.

Distance & flight times: La Guardia to Midway International Airport

The shortest flight time between LGA and MDW is 2 hours and 30 minutes.

ViaTotal flight timeLayover timeDistance
Direct2h 30m-727 miles (1170 km)
DTW Detroit5h 29m2h 44m731 miles (1176 km)
STL Saint Louis6h 3m2h 20m1142 miles (1837 km)
BNA Nashville6h 20m1h 45m1164 miles (1873 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.LGA-MDW flight routesNew York to Chicago flight routes illustrated on a map.
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New York - Chicago route map and flight paths
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You can fly non-stop from New York (LGA) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 2 hours and 30 minutes. If you travel with a connecting flight instead, for example via Detroit, the total flight time will be 5 hours and 29 minutes.

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

The flight time between La Guardia (LGA) and Chicago Midway International (MDW) is approximately 2 hours and 30 minutes. The distance between the two airports is 731 miles (or 1176 kilometers).

Yes, you can fly non-stop to MDW from LGA 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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