Find Cheap Flights to Chicago (MDW) Starting from $363

Good to Know: Flights to MDW

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

Cheapest Round Trip Flight

$567

WN Southwest Airlines • nonstop • 3h 55m

Jun 29 – Jul 06

The cheapest round trip flight from San Antonio to Chicago (SAT-MDW-SAT) is currently $567

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Cheapest One way Flight

$861

WN Southwest Airlines • 4 stops • 40h 35m

Jun 29

The cheapest one way flight from Belize City to Chicago (BZE-MDW) is currently $861

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Cheapest Direct Flight

$363

WN Southwest Airlines • nonstop • 4h 5m

Jul 01

The cheapest nonstop flight from Orlando to Chicago (MCO-MDW) is currently $363

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Fastest Flight

3h 55m

The fastest nonstop flight from San Antonio to Chicago (SAT-MDW) takes 3h 55m

Top Airlines Flying to Chicago Midway International (MDW)

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

WestJet Airlines

WestJet Airlines

Lufthansa Airline (LH)

Lufthansa Airlines

Air India, AI

Air India

Qatar Airways-QR

Qatar Airways

Air Canada-AC

Air Canada

Etihad Airways-EY

Etihad Airways

Best Flight Deals to Chicago

Identify the most efficient round-trip flights to Chicago. We present options balancing cost and convenience for your return journey.

Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
3h 55m
3:20 PM - 5:55 PM • nonstop
WN
San Antonio → Chicago
11h 55m
12:20 PM - 7:35 PM • 1 stop
$567
Southwest Airlines
Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
10h 50m
12:25 PM - 7:15 PM • 1 stop
WN
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
$567
Southwest Airlines
Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
8h 40m
1:50 PM - 7:10 PM • 1 stop
WN
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
$567
Southwest Airlines
Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
10h 55m
5:45 PM - 12:40 AM • 1 stop
WN
San Antonio → Chicago
4h
10:35 AM - 1:15 PM • nonstop
$567
Southwest Airlines
Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
10h 15m
12:50 PM - 7:05 PM • 1 stop
WN
San Antonio → Chicago
4h 5m
9:25 PM - 12:10 AM • nonstop
$567
Southwest Airlines
Jun 29 - Jul 06, Economy
WN
San Antonio → Chicago
7h 10m
5:25 PM - 9:55 PM • 1 stop
WN
San Antonio → Chicago
4h
10:35 AM - 1:15 PM • nonstop
$567
Southwest Airlines

Fly to Chicago Easily with the Best Airfare Deals on FareLeaders

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.

FAQs on 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 861
What are the most popular origin to Chicago (MDW)?
Travelers frequently travel from Orlando, San Antonio, Belize City to Chicago (MDW)

Airport Information: Chicago Midway International (MDW)

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

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