Score Cheap Flights from MDW: Compare Now

Good to Know: Cheapest and Fastest Flights from MDW

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

Cheapest Round Trip Flight

$469

WN Southwest Airlines • 1 stop • 20h 45m

Dec 27 – Dec 28

The cheapest round trip flight from Chicago to Phoenix (MDW-PHX-MDW) is currently $469

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Cheapest One way Flight

$209

DL Delta Airlines • 1 stop • 10h 41m

Aug 11

The cheapest one way flight from Chicago to Orlando (MDW-MCO) is currently $209

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Cheapest Direct Flight

$118

WN Southwest Airlines • nonstop • 5h 55m

Dec 28

The cheapest nonstop flight from Chicago to Phoenix (MDW-PHX) is currently $118

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Fastest Flight

5h 50m

The fastest nonstop flight from Chicago to Phoenix (MDW-PHX) takes 5h 50m

Top Airlines Flying from Chicago Midway International (MDW)

Southwest Airlines-WN

Southwest Airlines

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

Sun Country Airlines (SY)

Sun Country Airlines

WestJet Airlines

WestJet Airlines

American Airlines, AA

American Airlines

Alaska Airlines -AS

Alaska Airlines

Aeromexico Airline (AM)

Aeromexico

Virgin Atlantic (VS)

Virgin Atlantic

Most Recent Flight Deals from Chicago Now!

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

Dec 27 - Dec 28, Economy
WN
Chicago → Phoenix
20h 45m
5:10 AM - 4:55 PM • 1 stop
WN
Chicago → Phoenix
5h 15m
5:05 AM - 9:20 AM • nonstop
$469
Southwest Airlines
Dec 27 - Dec 28, Economy
WN
Chicago → Phoenix
9h 5m
9:55 AM - 2:40 PM • 1 stop
WN
Chicago → Phoenix
12h
9:35 AM - 5:55 PM • 2 stops
$568
Southwest Airlines
Aug 09 - Aug 16, Economy
WN
Chicago → Anchorage
19h 10m
12:25 PM - 9:15 PM • 1 stop
WN
Chicago → Anchorage
25h 30m
11:55 PM - 6:25 PM • 1 stop
$588
Southwest Airlines
Aug 09 - Aug 16, Economy
WN
Chicago → Anchorage
19h 5m
12:30 PM - 9:15 PM • 2 stops
WN
Chicago → Anchorage
17h 5m
10:25 PM - 11:50 AM • 1 stop
$594
Southwest Airlines
Aug 09 - Aug 16, Economy
WN
Chicago → Anchorage
20h 35m
11:40 AM - 9:15 PM • 2 stops
WN
Chicago → Anchorage
24h 5m
10:25 PM - 4:10 PM • 1 stop
$594
Southwest Airlines
Dec 27 - Dec 28, Economy
DL
Chicago → Phoenix
10h 23m
5:59 PM - 11:22 PM • 1 stop
DL
Chicago → Phoenix
12h 35m
11:50 PM - 8:45 AM • 1 stop
$842
Delta Airlines

Affordable Worldwide Flights from Chicago Midway International (MDW)

Looking for cheap last-minute flight deals or the best round-trip flight from Chicago? Find the biggest savings on one-way and round-trip tickets right here. Search and compare low-cost domestic airfares and international flight deals from MDW to all the popular destinations of the world using our flight search and compare platform. Some top destinations where people fly most from Chicago are Las Vegas, Las Vegas, Fort Lauderdale, Los Angeles, Cancún and more.

FAQs on Flights from Chicago (MDW)

Which airlines fly from Chicago?
Airlines flying the most from Chicago (MDW)
What are the most popular destination from Chicago ( MDW )?
Travelers frequently travel to Orlando, Phoenix, Anchorage from Chicago

Essential Information for Booking Flights from Chicago (MDW) - AI Insights

What's the cheapest airline from mdw?
You can find cheap airline tickets from Chicago Midway International Airport (mdw) on Frontier Airlines. As a business class passenger, you'll enjoy priority check-in, lounge access, and flatbed seats. Booking in advance, 29 days prior to your trip, may help secure the best fares for your one-way flight.
What's the popular airline to fly from mdw?
You can fly from Chicago Midway International Airport (mdw) to your destination on Southwest Airlines. As a business class passenger, you'll enjoy priority check-in, lounge access, and flatbed seats. Please note that this is a one-way trip with two stops. It's recommended to book at least 29 days in advance for the best fares. You can find affordable airfare options by visiting our website or checking out cheap flights on our agency.
What's the cheapest day of the week to fly from mdw?
The cheapest day to fly from Chicago Midway International Airport (mdw) is Saturday. Flying on Saturdays can result in lower fares compared to other days of the week.
What's the cheapest month to fly from mdw?
The cheapest month to fly from Chicago Midway International Airport (mdw) is November. Flying during this time can help you save on airfares, as it's considered a low season for air travel. You can find budget-friendly flights with priority service and lounge access in Business class.
Which airline/airlines fly from mdw?
Allegiant Airlines offers flights from Chicago Midway International Airport (mdw) to various destinations. For a business class ticket on this route, advance booking is recommended at least 29 days in advance to secure your preferred cabin type. You can find the cheapest airfares and budget-friendly options by visiting our website.
What are the available flights from Chicago Midway International Airport to Milwaukee?
You can find available flights from Chicago Midway International Airport to Milwaukee on fareleaders.com, which offers a comprehensive flight comparison platform. Simply enter your travel dates and preferred airline, and our website will provide you with a list of available flights, including prices and schedules.
How can I book my airfare on fareleaders.com for my July trip?
To book your airfare on fareleaders.com, simply click on the 'Book Now' button after selecting your preferred flight. Our website will guide you through the booking process, ensuring a seamless and secure transaction.
Can I get the best fares and deals on flights via fareleaders.com?
Yes, fareleaders.com offers exclusive discounts and promotions for advance bookings of 29 days or more. By booking in advance, you can save up to 20% on your airfare. Don't miss out on these amazing deals!
Is it possible to compare airlines and their flight schedules on your website?
Absolutely! fareleaders.com provides a user-friendly interface that allows you to compare airlines and their flight schedules in real-time. Simply enter your travel dates and preferred airport, and our website will display a list of available flights, including schedules and prices.
Do you offer any discounts or promotions for advance bookings of 29 days or more?
Yes, fareleaders.com offers exclusive discounts for advance bookings of 29 days or more. By booking in advance, you can save up to 20% on your airfare. Don't miss out on these amazing deals!
Can I get information about my flight itinerary, including check-in and baggage details, on fareleaders.com?
Yes, fareleaders.com provides detailed information about your flight itinerary, including check-in and baggage details. Simply log in to your account or contact our customer support team for assistance.

Airport Information: Chicago Midway International (MDW)

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

Chicago (MDW) Arrivals and Departures

Airline Flight code Arrival time Status
None
United Airlines
UAL1990
A319
3rd Aug, 2026 9:00 PM
Arriving
None
SkyWest Airlines
SKW6380
CRJ7
3rd Aug, 2026 8:50 PM
Arriving
None
SkyWest Airlines
SKW5588
E75L
3rd Aug, 2026 8:57 PM
Arriving
None
American Airlines
AAL1592
B738
3rd Aug, 2026 8:59 PM
Arriving
None
SkyWest Airlines
SKW6013
CRJ2
3rd Aug, 2026 9:00 PM
Arriving
None
United Airlines
UAL1564
A320
3rd Aug, 2026 9:00 PM
Arriving
None
SkyWest Airlines
SKW4679
E75L
3rd Aug, 2026 8:56 PM
Arriving
None
United Airlines
UAL1084
A320
3rd Aug, 2026 9:00 PM
Arriving
None
Southwest Airlines
SWA596
B738
3rd Aug, 2026 8:57 PM
Arriving
None
American Airlines
AAL752
B738
3rd Aug, 2026 9:00 PM
Arriving

More Flight Options from Chicago, MDW

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