Is Southwest the cheapest airline to fly with from Los Angeles to Chicago Midway Airport?

With an average price of $344 return, Southwest is not the cheapest airline to fly from Los Angeles to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $215 on average.

Does Southwest fly direct to Chicago Midway Airport from Los Angeles?

Yes, Southwest does offer direct flights for the route, with around 25 flights per week.

What’s the cheapest day of the week to fly from Los Angeles to Chicago Midway Airport with Southwest?

On average, the cheapest day of the week to fly from Los Angeles to Chicago Midway Airport with Southwest is Tuesday, when prices are around $89. The most expensive day is generally Saturday, where the average price is around $150.

What’s the cheapest month to fly from Los Angeles to Chicago Midway Airport with Southwest?

The cheapest month for Southwest flights to Chicago Midway Airport from Los Angeles is generally April, where plane tickets cost $183 on average. If possible, try to avoid the most expensive months of February and December, where tickets cost $253 and $256 respectively.

$90 Cheap Southwest Flights from Los Angeles to Chicago Midway Airport

LAX - MDW

Search hundreds of travel sites at once for deals on Southwest flights from Los Angeles to Chicago Midway Airport

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals

Cheap Southwest Flight Deals from Los Angeles to Chicago Midway Airport

Here are some of the best deals found on KAYAK recently from Southwest for round-trip flights from Los Angeles to Chicago Midway Airport that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip Southwest flight deals from Los Angeles to Chicago Midway Airport

Thu, Nov 13 - Sun, Nov 16

10:45 am - 4:40 pmLAX-MDW

3h 55mnonstop

6:05 am - 8:35 amMDW-LAX

4h 30mnonstop

$179Southwest

Find Deal

Wed, Dec 3 - Sat, Dec 13

6:00 am - 12:05 pmLAX-MDW

4h 05mnonstop

9:25 am - 3:50 pmMDW-LAX

8h 25m1 stop

$189Southwest

Find Deal

Sat, Dec 6 - Sun, Dec 14

5:05 am - 3:20 pmLAX-MDW

8h 15m2 stops

6:05 am - 8:35 amMDW-LAX

4h 30mnonstop

$194Southwest

Find Deal

Fri, Dec 5 - Fri, Dec 12

9:00 pm - 5:05 amLAX-MDW

6h 05m1 stop

9:45 pm - 12:10 amMDW-LAX

4h 25mnonstop

$206Southwest

Find Deal

Fri, Dec 5 - Mon, Dec 8

11:00 pm - 5:00 amLAX-MDW

4h 00mnonstop

1:25 pm - 6:25 pmMDW-LAX

7h 00m1 stop

$210Southwest

Find Deal

Fri, Dec 5 - Mon, Dec 8

11:00 pm - 5:00 amLAX-MDW

4h 00mnonstop

4:15 pm - 6:40 pmMDW-LAX

4h 25mnonstop

$213Southwest

Find Deal

Sun, Dec 7 - Mon, Dec 8

6:45 am - 12:40 pmLAX-MDW

3h 55mnonstop

1:25 pm - 6:25 pmMDW-LAX

7h 00m1 stop

$217Southwest

Find Deal

Sat, Nov 8 - Sun, Nov 9

9:20 am - 4:45 pmLAX-MDW

5h 25m1 stop

9:25 am - 12:00 pmMDW-LAX

4h 35mnonstop

$218Southwest

Find Deal

Wed, Dec 3 - Wed, Dec 10

11:00 pm - 5:00 amLAX-MDW

4h 00mnonstop

8:55 pm - 11:25 pmMDW-LAX

4h 30mnonstop

$219Southwest

Find Deal

Fri, Nov 14 - Mon, Nov 17

2:35 pm - 10:05 pmLAX-MDW

5h 30m1 stop

8:55 pm - 11:25 pmMDW-LAX

4h 30mnonstop

$222Southwest

Find Deal

Useful Info

Low season	February
High season	July
Cheapest flight	$90
Average price round-trip	$307
Good deal one-way	$185

Best time to beat the crowds with an average 16% drop in price.

Most popular time to fly and prices are also 3% lower on average.

Flight from Los Angeles to Chicago Midway Airport

(avg. price over the last 2 weeks)

or less

When to Book Flights with Southwest from Los Angeles to Chicago Midway Airport

Average price per month

Flight prices as travel date approaches

Is Southwest the cheapest airline to fly with from Los Angeles to Chicago Midway Airport?
With an average price of $344 return, Southwest is not the cheapest airline to fly from Los Angeles to Chicago Midway Airport with. Instead, for the lowest price, our data suggests flying with Spirit Airlines, where a return flight costs $215 on average.
What is the cheapest Southwest flight from Los Angeles to Chicago Midway Airport?
In the last 3 days, the lowest price for a flight with Southwest from Los Angeles to Chicago Midway Airport was $219 for a return flight and $98 for a one-way flight.
Does Southwest fly direct to Chicago Midway Airport from Los Angeles?
Yes, Southwest does offer direct flights for the route, with around 25 flights per week.
What’s the cheapest day of the week to fly from Los Angeles to Chicago Midway Airport with Southwest?
On average, the cheapest day of the week to fly from Los Angeles to Chicago Midway Airport with Southwest is Tuesday, when prices are around $89. The most expensive day is generally Saturday, where the average price is around $150.
What’s the cheapest month to fly from Los Angeles to Chicago Midway Airport with Southwest?
The cheapest month for Southwest flights to Chicago Midway Airport from Los Angeles is generally April, where plane tickets cost $183 on average. If possible, try to avoid the most expensive months of February and December, where tickets cost $253 and $256 respectively.

8.0

Very good4,239 verified ratings

8.1Boarding

7.0Food

8.0Comfort

8.6Crew

7.5Entertainment

Pros +

Cons -

Show reviews that mention

2.0 Poor

Verified traveler, Oct 2025

DAL-LIT

Delayed 5.5 hours

10.0 Wonderful

Verified traveler, Oct 2025

BOS-BWI

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

8.0 Very good

Verified traveler, Oct 2025

MHT-MDW

Getting worse with new changes.

4.0 Mediocre

Jeff, Oct 2025

MCI-SAN

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

4.0 Mediocre

Thomas, Oct 2025

STL-CMH

Internet was not functioning.

2.0 Poor

Thomas, Oct 2025

SAT-STL

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

10.0 Wonderful

Lynda, Oct 2025

VPS-BNA

On time. Communication good. Smooth flight

2.0 Poor

Princess, Oct 2025

MSY-DAL

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

6.0 Okay

Thomas, Oct 2025

DAL-SAT

Late again.

6.0 Okay

Thomas, Oct 2025

CMH-DAL

Just the usual delays

Everything you need to know for your flight from Los Angeles to Chicago Midway Airport

Cabin class

Complete your trip

Flights to other cities

Return flight deals

Southwest flights

Cabin class types available on flights to Chicago Midway Airport

First Class flights from Los Angeles to Chicago Midway Airport

Business Class flights from Los Angeles to Chicago Midway Airport

Prem Econ Class flights from Los Angeles to Chicago Midway Airport

Economy Class flights from Los Angeles to Chicago Midway Airport

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

LAX - MDW

$90 Find Cheap Southwest Flights from Los Angeles to Chicago Midway Airport

Search hundreds of travel sites at once for deals on Southwest flights from Los Angeles to Chicago Midway Airport

Cheap Southwest Flight Deals from Los Angeles to Chicago Midway Airport

Recent round-trip Southwest flight deals from Los Angeles to Chicago Midway Airport

Recent one-way Southwest flight deals from Los Angeles to Chicago Midway Airport

Recent last minute Southwest flight deals from Los Angeles to Chicago Midway Airport

Recent direct Southwest flight deals from Los Angeles to Chicago Midway Airport

Good to know

When to Book Flights with Southwest from Los Angeles to Chicago Midway Airport

FAQs for flying to Chicago Midway Airport with Southwest

Is Southwest the cheapest airline to fly with from Los Angeles to Chicago Midway Airport?

What is the cheapest Southwest flight from Los Angeles to Chicago Midway Airport?

Does Southwest fly direct to Chicago Midway Airport from Los Angeles?

What’s the cheapest day of the week to fly from Los Angeles to Chicago Midway Airport with Southwest?

What’s the cheapest month to fly from Los Angeles to Chicago Midway Airport with Southwest?

Southwest Customer Reviews

Pros +

Cons -

Traveler rating:

Sort by:

Everything you need to know for your flight from Los Angeles to Chicago Midway Airport

Cabin class types available on flights to Chicago Midway Airport

Cabin classes available on flights to Los Angeles. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Complete your trip to Chicago Midway Airport with a hotel stay or car rental

Flights to other popular destinations

The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Find deals for your return flight

Top Southwest flights

The most popular destinations for flights with Southwest according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.