Cheap Flight Tickets from New York (LGA) to Chicago (MDW), Starting at $169

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

$224

WN Southwest Airlines • nonstop • 3h 40m

Oct 24 – Oct 29

The cheapest round trip flight from New York to Chicago (LGA-MDW-LGA) is currently $224

🔍 Search Flights

Cheapest One way Flight

$358

WN Southwest Airlines • 1 stop • 17h

Nov 01

The cheapest one way flight from New York to Chicago (LGA-MDW) is currently $358

🔍 Search Flights

Cheapest Direct Flight

$169

WN Southwest Airlines • nonstop • 3h 40m

Oct 29

The cheapest nonstop flight from New York to Chicago (LGA-MDW) is currently $169

🔍 Search Flights

Fastest Flight

3h 40m

The fastest nonstop flight from New York to Chicago (LGA-MDW) takes 3h 40m

Top Airlines Flying from New York to Chicago

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta 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.

Oct 24 - Oct 29, Economy
WN
New York → Chicago
3h 40m
4:35 PM - 5:55 PM • nonstop
WN
New York → Chicago
3h 30m
2:40 PM - 5:50 PM • nonstop
$224
Southwest Airlines
Oct 24 - Oct 29, Economy
WN
New York → Chicago
3h 40m
4:35 PM - 5:55 PM • nonstop
WN
New York → Chicago
8h 55m
7:50 AM - 2:25 PM • 1 stop
$228
Southwest Airlines
Oct 24 - Oct 29, Economy
WN
New York → Chicago
11h 55m
4:05 PM - 10:20 PM • 1 stop
WN
New York → Chicago
3h 30m
7:35 PM - 10:45 PM • nonstop
$228
Southwest Airlines
Oct 24 - Oct 29, Economy
WN
New York → Chicago
8h 30m
5:35 PM - 9:45 PM • 1 stop
WN
New York → Chicago
3h 25m
12:55 PM - 4:00 PM • nonstop
$228
Southwest Airlines
Oct 24 - Oct 29, Economy
WN
New York → Chicago
15h 25m
1:20 PM - 9:45 PM • 1 stop
WN
New York → Chicago
3h 25m
5:10 AM - 8:15 AM • nonstop
$228
Southwest Airlines
Oct 24 - Oct 29, Economy
WN
New York → Chicago
8h 30m
5:35 PM - 9:45 PM • 1 stop
WN
New York → Chicago
8h 35m
9:50 AM - 4:05 PM • 1 stop
$232
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 6:45 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 369
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 8:55 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

More Flight Options for New York (LGA) and Chicago (MDW)

Why Fareleaders for LGA to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on New York to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on LGA to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of New York to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the New York (LGA) to Chicago (MDW)
Terms and Conditions*