Cheap Flight Tickets from New York (LGA) to Chicago (MDW), Starting at $385

Good to Know: Cheapest and Fastest LGA - MDW Flights

Useful information for finding best airline tickets from La Guardia to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$385

WN Southwest Airlines • nonstop • 3h 35m

Aug 30 – Sep 04

The cheapest round trip flight from New York to Chicago (LGA-MDW-LGA) is currently $385

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Cheapest Direct Flight

$385

WN Southwest Airlines • nonstop • 3h 35m

Aug 30

The cheapest nonstop flight from New York to Chicago (LGA-MDW) is currently $385

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Fastest Flight

3h 35m

The fastest nonstop flight from New York to Chicago (LGA-MDW) takes 3h 35m

Top Airlines Flying from New York to Chicago

Southwest Airlines-WN

Southwest Airlines

Latest Flight Deals from New York (LGA) to Chicago (MDW)

Compare and book low fare round-trip air tickets from New York to Chicago. Ideal for travelers with confirmed return itineraries.

Aug 30 - Sep 04, Economy
WN
New York → Chicago
3h 35m
9:35 PM - 10:50 PM • nonstop
WN
New York → Chicago
3h 25m
12:50 PM - 3:55 PM • nonstop
$385
Southwest Airlines
Aug 30 - Sep 04, Economy
WN
New York → Chicago
3h 40m
7:20 AM - 8:40 AM • nonstop
WN
New York → Chicago
3h 25m
5:15 PM - 8:20 PM • nonstop
$385
Southwest Airlines
Aug 30 - Sep 04, Economy
WN
New York → Chicago
3h 40m
7:20 AM - 8:40 AM • nonstop
WN
New York → Chicago
10h 15m
5:55 AM - 1:10 PM • 1 stop
$395
Southwest Airlines
Aug 30 - Sep 04, Economy
WN
New York → Chicago
12h 20m
5:30 PM - 12:10 AM • 1 stop
WN
New York → Chicago
3h 25m
7:50 PM - 10:55 PM • nonstop
$395
Southwest Airlines
Aug 30 - Sep 04, Economy
WN
New York → Chicago
12h 35m
4:55 PM - 11:50 PM • 1 stop
WN
New York → Chicago
3h 20m
5:00 AM - 8:00 AM • nonstop
$395
Southwest Airlines
Aug 30 - Sep 04, Economy
WN
New York → Chicago
10h 15m
1:30 PM - 6:45 PM • 1 stop
WN
New York → Chicago
3h 30m
8:15 AM - 11:25 AM • nonstop
$395
Southwest Airlines

Fly from New York to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from New York to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on New York to Chicago Flights

What are the airports in New York?
JFK,LGA,EWR
What’s the most popular airline flying from LGA to MDW?
The most popular airline flying from New York to Chicago are
Can I fly from LGA to MDW non-stop?
Yes, you can fly LGA to MDW non-stop on
Which airlines fly nonstop between New York and Chicago?
The non-stop flights between New York and Chicago are .
What’s the earliest departure time from LGA to MDW Airport?
The earliest flight leaves LGA at 6:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my New York to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from LGA to MDW?
Read the fare rules of the New York to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from New York and Chicago?
operate flights between New York and Chicago
How long does a flight from New York to Chicago take?
It takes approximately 2 hour to fly non-stop from LGA to MDW, which is 725.08 miles by air.
Which airlines provide the cheapest flights from New York (LGA) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from LGA were found on WN : USD 395
Do I need a passport to fly between LGA and MDW?
No
What’s the latest departure time from LGA to MDW ?
The last flight leaves LGA at 9:35 pm

New York (LGA) to Chicago (MDW): Airport Information

Origin Airport La Guardia , New York, US
Destination Airport Chicago Midway International , Chicago, US
Distance 725 miles

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