Search Flights to Chicago (MDW)

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

$284

WNSouthwest Airlines• 1 stop • 10h 25m

Oct 13 – Oct 20

The cheapest round trip flight from Dallas Love Field to Chicago Midway International is currently $284

🔍 Search Flights

Cheapest Direct Flight

$370

NKSpirit Airlines• nonstop• 3h 46m

Oct 13

The cheapest nonstop flight from Dallas Love Field to Chicago Midway International is currently $370

🔍 Search Flights

Fastest Flight

3h 30m

The fastest nonstop flight from Dallas Love Field to Chicago Midway International takes 3h 30m

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.

Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
10h 25m
2:25 PM - 8:50 PM • 1 stop
WN
Dallas → Chicago
3h 40m
3:30 PM - 5:50 PM • nonstop
$284
Southwest Airlines
Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
12h 35m
12:55 PM - 8:50 PM • 1 stop
WN
Dallas → Chicago
3h 40m
3:30 PM - 5:50 PM • nonstop
$284
Southwest Airlines
Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
3h 30m
12:15 PM - 2:25 PM • nonstop
WN
Dallas → Chicago
10h
5:05 PM - 11:05 PM • 2 stops
$289
Southwest Airlines
Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
8h 35m
2:25 PM - 7:40 PM • 1 stop
WN
Dallas → Chicago
5h 55m
5:05 PM - 9:00 PM • 1 stop
$458
Southwest Airlines
Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
7h 20m
1:20 PM - 6:00 PM • 1 stop
WN
Dallas → Chicago
7h 25m
6:20 PM - 11:05 PM • 1 stop
$497
Southwest Airlines
Oct 13 - Oct 20, Economy
WN
Dallas → Chicago
7h 15m
2:25 PM - 7:00 PM • 1 stop
WN
Dallas → Chicago
7h 15m
7:50 AM - 12:25 PM • 1 stop
$541
Southwest Airlines

Compare & Book Cheapest 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.

Essential Information for Booking Flights from () - AI Insights

What's the cheapest airline to mdw?
Sky Airline Perú (H8), China Eastern Airlines (MU), Air Serbia (JU), VRG Linhas Aereas S.A. (G3), Porter Airline (PD), and other options are currently available for flights to Chicago Midway International (mdw) with one passenger, offering budget-friendly fares.
What's the popular airline to fly to mdw?
Delta Airlines (DL) offers popular routes to Milwaukee, Wisconsin (mdw), and is frequently cited as a good option for affordable flights to Chicago Midway International Airport (mdw).
What's the cheapest day of the week to fly to mdw?
Tuesday is the cheapest day to fly to Milwaukee, Wisconsin.
What's the cheapest month to fly to mdw?
April offers the most affordable flights to Milwaukee, Wisconsin.
What is the cheapest airline to fly from Chicago Midway International to Milwaukee?
Sky Airline Perú (H8) offers the lowest fares for flights to Milwaukee from Chicago Midway International.
When does the cheapest flight to Milwaukee typically operate?
The cheapest flights to Milwaukee typically operate on Tuesdays.
What is the name of the airport in Milwaukee that is often used for low-cost flights?
Milwaukee – William Sabin Memorial Airport (MKE)

Destination Airport Information

IATA CodeMDW
NameChicago Midway International
CityChicago
CountryUS
Latitude41.7859992980957
Longitude-87.75240325927734

Popular Airlines

Southwest Airlines (WN)
Spirit Airlines (NK)
Delta Airline (DL)
United Airlines (UA)
American Airlines (AA)

More Flight Options to Chicago, MDW

Why Fareleaders for Flights to MDW

Lowest Prices
Lowest Prices
Find the lowest MDW airfares by comparing hundreds of airlines and agencies.
New Deals
New Deals Everyday
Never miss a deal on MDW flights—we update prices daily to bring you the best airfares.
Best Travel Options
Best Travel Options
Compare hundreds of MDW flights and find the best deals without any added service charges.
Get Fare Drop Alert
Be the first to know when fares drop to Chicago (MDW)
Terms and Conditions*