$99 Cheap Flights from Los Angeles (LAX) to Chicago (MDW)

View $99 flight on Wed, Aug 20, 2025Opens in a new window

Popular airlines from Los Angeles Intl. (LAX) to Chicago Midway Airport (MDW)

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Cheap Flights from Los Angeles to Chicago (LAX-MDW)

Prices were available within the past 7 days and start at $99 for one-way flights and $194 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Aug 7 - Sat, Aug 16
LAX
Los Angeles
MDW
Chicago
$194 Roundtrip, found 3 days ago
$194
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, Aug 7 from Los Angeles to Chicago, returning Sat, Aug 16, priced at $194 found 3 days ago
Southwest Airlines
Wed, Sep 3 - Sat, Sep 6
LAX
Los Angeles
MDW
Chicago
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Sep 3 from Los Angeles to Chicago, returning Sat, Sep 6, priced at $197 just found
Southwest Airlines
Wed, Aug 6 - Wed, Aug 20
LAX
Los Angeles
MDW
Chicago
$198 Roundtrip, found 13 hours ago
$198
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Wed, Aug 6 from Los Angeles to Chicago, returning Wed, Aug 20, priced at $198 found 13 hours ago
Southwest Airlines
Wed, Aug 6 - Sat, Aug 9
LAX
Los Angeles
MDW
Chicago
$199 Roundtrip, just found
$199
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 6 from Los Angeles to Chicago, returning Sat, Aug 9, priced at $199 just found
Southwest Airlines
Wed, Aug 20 - Sun, Aug 24
LAX
Los Angeles
MDW
Chicago
$205 Roundtrip, just found
$205
Roundtrip
just found
Select Southwest Airlines flight, departing Wed, Aug 20 from Los Angeles to Chicago, returning Sun, Aug 24, priced at $205 just found
Southwest Airlines
Wed, Sep 3 - Thu, Sep 11
LAX
Los Angeles
MDW
Chicago
$206 Roundtrip, found 1 day ago
$206
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Los Angeles to Chicago, returning Thu, Sep 11, priced at $206 found 1 day ago
Southwest Airlines
Sat, Aug 2 - Sat, Aug 9
LAX
Los Angeles
MDW
Chicago
$209 Roundtrip, just found
$209
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Aug 2 from Los Angeles to Chicago, returning Sat, Aug 9, priced at $209 just found
Southwest Airlines
Wed, Sep 24 - Mon, Sep 29
LAX
Los Angeles
MDW
Chicago
$211 Roundtrip, found 1 hour ago
$211
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Wed, Sep 24 from Los Angeles to Chicago, returning Mon, Sep 29, priced at $211 found 1 hour ago
Frontier Airlines
Thu, Oct 23 - Thu, Oct 30
LAX
Los Angeles
MDW
Chicago
$211 Roundtrip, found 2 days ago
$211
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Oct 23 from Los Angeles to Chicago, returning Thu, Oct 30, priced at $211 found 2 days ago
Delta
Thu, Sep 25 - Sun, Sep 28
LAX
Los Angeles
MDW
Chicago
$235 Roundtrip, just found
$235
Roundtrip
just found
Select Delta flight, departing Thu, Sep 25 from Los Angeles to Chicago, returning Sun, Sep 28, priced at $235 just found

Find the cheapest month to fly from Los Angeles (LAX) to Chicago (MDW)

February is typically the cheapest month to fly

From $118 - $317 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $170
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $170
Flights from Los Angeles (LAX) to Chicago (MDW)
Origin airport
Los Angeles Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$194
Distance
1747 mi
Average flight time
6 hours 37 mins

Los Angeles to Chicago Flights

The cheapest times to fly from Los Angeles to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Los Angeles to Chicago are during the month of August. You can find some of the cheapest flights from Los Angeles to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Los Angeles to Chicago

Sunday is one of the best days to book for cheap flights from Los Angeles to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Los Angeles to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Los Angeles to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $99 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Los Angeles to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Los Angeles to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW) cost?
Pick up cheap return fares starting at $159 from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW). This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and Spirit Airlines flight leaving LAX on July 22 2025 and touching down at MDW. The price was last updated on July 1 2025 and has not changed since.
What is the cheapest month to fly from LAX to MDW?
To score a cheap fare, look for direct flights from LAX to MDW jetting off in November. You can find a one-way Southwest Airlines flight for $99 leaving on November 19 2025. This price is based on the cheapest direct flight found on Expedia for this route in the next 330 days. The price was last updated on July 1 2025 and remains unchanged.
Which airlines fly direct from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
Jump on a direct flight with Southwest Airlines and journey straight from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW).
What is the cheapest airline that flies from LAX to MDW?
Jet off from LAX to MDW with Southwest Airlines. This airline currently offers the cheapest one-way fare on this route, starting at $99. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from LAX on September 24 2025. Prices were last updated on July 1 2025 and have not changed since.
How many flights per day from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
Every day on average, 2 direct flights take off from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW). Choose the departure time that best fits your schedule.
What are the most popular departure times for flights from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
More travelers fly between LAX and MDW at 2 PM than at any other time. Looking to skip the crowds? Try choosing a quieter departure window and you could save on your fare as well.
What day of the week has the most flights from LAX to MDW?
If you depart on a Thursday, you'll get the largest range of options for flights from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW).
What is the earliest flight from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
Los Angeles Intl. Airport (LAX)'s first flight to Midway Intl. Airport (MDW) departs at approximately 6:00AM UTC-8. With a total travel time of 4h, you'll land at around 12:00PM UTC-6.
How long does it take to fly from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
It takes around 3 hours and 58 minutes to cover the 1,750 mi from LAX to MDW.
What is the best time to fly from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
To touch down at Midway Intl. Airport (MDW) on schedule, opt for a flight that leaves Los Angeles Intl. Airport (LAX) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this time.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Los Angeles Intl. Airport (LAX)?
Take a direct flight from Los Angeles Intl. Airport (LAX) to Chicago and land at O'Hare Intl. Airport (ORD). Another gateway to this destination is Midway Intl. Airport (MDW).
Is it cheaper to buy a plane ticket from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW) last-minute?
Last-minute fares from LAX to MDW are usually more expensive. For the cheapest rates, start searching for flights ahead of time. That said, if you're flexible with your travel plans, it's possible to land a cheap fare right before your trip.
Is it cheaper to book a LAX to MDW flight and hotel package?
Compared with arranging flights and hotels separately, booking a LAX to MDW flight and hotel package with Expedia could result in significant savings. What's more, having everything in one convenient place takes the hassle out of travel planning. Simply secure your flights and choose from our extensive range of hotels, then personalize your trip with extras like tours and car rentals.
Can I cancel or change the date of my flight from Los Angeles Intl. Airport (LAX) to Midway Intl. Airport (MDW)?
It's generally possible to cancel or reschedule your LAX to MDW flight. However, for bookings made more than 24 hours ago, additional charges may apply. Refer to your airline's policies in your itinerary to see what changes are possible and if any costs are involved. You'll also find further details on our Customer Service portal.

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