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Cheap Flights to Chicago (MDW)

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

Good to know

Useful information for finding cheap flights to Chicago Midway International and booking your next trip

Cheapest Round Trip Flight

$537

WN Southwest Airlines • nonstop • 3h 45m

Jun 27 – Jun 29

The cheapest round trip flight from La Guardia to Chicago Midway International is currently $537

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Cheapest Direct Flight

$310

WN Southwest Airlines • nonstop • 3h 40m

Jun 27

The cheapest nonstop flight from La Guardia to Chicago Midway International is currently $310

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Fastest Flight

3h 40m

The fastest nonstop flight from La Guardia to Chicago Midway International takes 3h 40m

Flight deals to Chicago

Jun 27 - Jun 29, Economy
WN
New York → Chicago
3h 45m
3:35 PM - 5:00 PM • nonstop
WN
New York → Chicago
3h 25m
6:15 AM - 9:20 AM • nonstop
$537
Southwest Airlines
Jun 27 - Jun 29, Economy
WN
New York → Chicago
3h 45m
2:00 PM - 3:25 PM • nonstop
WN
New York → Chicago
3h 30m
8:15 PM - 11:25 PM • nonstop
$537
Southwest Airlines
Jun 27 - Jun 29, Economy
WN
New York → Chicago
8h 55m
12:35 PM - 5:10 PM • 1 stop
WN
New York → Chicago
3h 25m
6:15 AM - 9:20 AM • nonstop
$547
Southwest Airlines
Jun 27 - Jun 29, Economy
WN
New York → Chicago
10h 55m
3:30 PM - 9:25 PM • 1 stop
WN
New York → Chicago
3h 25m
6:15 AM - 9:20 AM • nonstop
$547
Southwest Airlines
Jun 27 - Jun 29, Economy
WN
New York → Chicago
3h 45m
9:45 PM - 11:10 PM • nonstop
WN
New York → Chicago
7h 20m
7:40 AM - 1:20 PM • 1 stop
$547
Southwest Airlines
Jun 27 - Jun 29, Economy
WN
New York → Chicago
11h 40m
2:00 PM - 8:00 PM • 1 stop
WN
New York → Chicago
3h 25m
6:15 AM - 9:20 AM • nonstop
$547
Southwest Airlines

Facts to know while booking flights to Chicago (MDW)

Which airlines fly to Chicago?
Airlines flying the most to Chicago (MDW)
What is the cheapest flight to MDW Airport?
In the past couple of days, the cheapest tickets to MDW were found on ('WN') : USD 547
What are the most popular origin to Chicago (MDW)?
Travelers frequently travel from New York to Chicago (MDW)

Destination Airport Information

IATA Code MDW
Name Chicago Midway International
City Chicago
Country US
Latitude 41.7859992980957
Longitude -87.75240325927734

Popular Airlines

Southwest Airlines-WN
Delta Airline, DL

Popular Origin & Destination

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