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Type in your origin and destination city and we will give you the best flight route options based on flight time and connection time along with airline and airports delays.

Flights from New York to Chicago

LGA to MDW flights and routes map LGA to MDW. All flight routes from La Guardia, New York, USA to Chicago Midway International, Illinois, USA. These flights are operated by 4 different airlines. You can either fly non-stop with Southwest Airlines or choose from 4 different transit flights. The shortest flight time is 2 hours and 25 minutes.

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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5 routes with 1 stop found »
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Non-stop routes:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 3-8 flights per day.

SCHEDULE
2h 25m

Southwest Airlines
Non-stop with Southwest Airlines.
2h 25m
3-8 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 01m

Via Detroit DTW
1 stop with Delta Air Lines.
4h 01m
2-3 flights per day.
SCHEDULE
Via Saint Louis STL
1 stop with Southwest Airlines. 1-2 flights per day.

SCHEDULE
5h 30m

Via Saint Louis STL
1 stop with Southwest Airlines.
5h 30m
1-2 flights per day.
SCHEDULE
Via Nashville BNA
1 stop with Southwest Airlines. 1-4 flights per day.

SCHEDULE
6h 15m

Via Nashville BNA
1 stop with Southwest Airlines.
6h 15m
1-4 flights per day.
SCHEDULE
Via Raleigh/Durham RDU
1 stop with Frontier Airlines. 0-1 flights per day.
Ends in May 2024

SCHEDULE
6h 43m

Ends in May 2024
Via Raleigh/Durham RDU
1 stop with Frontier Airlines.
6h 43m
0-1 flights per day.
Ends in May 2024
SCHEDULE
Usually in time
Some delays
Usually delayed
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1 stop routes with codeshare or different airlines:

Duration

Via Detroit DTW With American Airlines & Delta Air Lines 0-1 flights per day.

SCHEDULE
6h 03m

Via Detroit DTW
6h 03m
With American Airlines & Delta Air Lines 0-1 flights per day.
SCHEDULE
Usually in time
Some delays
Usually delayed
SELECT DATE & CHECK PRICE
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New York to Chicago flights

With over 97 flights every week and 5 different airlines you have a wide option of flights to choose from. 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 Saint Louis, Detroit or any other of the 4 alternatives with flight connections.

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 am to 21 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 4 hours and 1 minutes and you can fly every weekday with departures between 6 am and 13 pm. Delta Air Lines is a member of SkyTeam.

With Frontier Airlines

If you fly from New York with Frontier Airlines you will do a stopover in Raleigh/Durham, RDU before reaching Chicago. This flight trip will take 6 hours and 43 minutes and you can fly every Monday or Wednesday with departures at 16:00.

Miles & flight time: LGA - MDW

The shortest flight time between LGA and MDW is 2 hours and 25 minutes.

ViaTotal flight timeLayover timeMiles
Direct2h 25m-727 (1170 km)
STL Saint Louis5h 30m1h 5m1142 (1837 km)
DTW Detroit6h 3m2h 42m731 (1176 km)
BNA Nashville6h 15m1h 50m1164 (1873 km)
RDU Raleigh/Durham6h 43m2h 52m1067 (1717 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.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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Unpublished Flight Rates From New York to Chicago

You can fly to Chicago (MDW) from New York (LGA) non-stop with Southwest Airlines. The flight takes approximately 2 hours and 25 minutes. If you travel with a connecting flight instead, for example via Saint Louis, the total flight time will be 5 hours and 30 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 Southwest Airlines, American Airlines, Delta Air Lines or Frontier Airlines.

The flight time between La Guardia, LGA and Chicago Midway International, MDW, is 2 hours and 25 minutes. The distance 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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