S$165 Cheap Flights from Los Angeles to Chicago

View S$165 flight on Mon, 25 Aug, 2025Opens in a new window

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 40% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

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

Prices were available within the past 7 days and start at S$165 for one-way flights and S$342 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Fri, 1 Aug - Fri, 8 Aug
LAX
Los Angeles
MDW
Chicago
S$342 Return, found 22 hours ago
S$342
Return
found 22 hours ago
Select Delta flight, departing Fri, 1 Aug from Los Angeles to Chicago, returning Fri, 8 Aug, priced at S$342 found 22 hours ago
Delta
Thu, 11 Sep - Sat, 13 Sep
LAX
Los Angeles
MDW
Chicago
S$421 Return, found 3 days ago
S$421
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Sep from Los Angeles to Chicago, returning Sat, 13 Sep, priced at S$421 found 3 days ago
Delta
Fri, 1 Aug - Fri, 8 Aug
LAX
Los Angeles
MDW
Chicago
S$434 Return, found 22 hours ago
S$434
Return
found 22 hours ago
Select Delta flight, departing Fri, 1 Aug from Los Angeles to Chicago, returning Fri, 8 Aug, priced at S$434 found 22 hours ago
Delta
Thu, 11 Sep - Sat, 13 Sep
LAX
Los Angeles
MDW
Chicago
S$480 Return, found 3 days ago
S$480
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Sep from Los Angeles to Chicago, returning Sat, 13 Sep, priced at S$480 found 3 days ago
Delta
Mon, 7 Jul - Thu, 10 Jul
LAX
Los Angeles
MDW
Chicago
S$493 Return, found 2 hours ago
S$493
Return
found 2 hours ago
Select Delta flight, departing Mon, 7 Jul from Los Angeles to Chicago, returning Thu, 10 Jul, priced at S$493 found 2 hours ago
Delta
Tue, 8 Jul - Wed, 9 Jul
LAX
Los Angeles
MDW
Chicago
S$511 Return, found 3 days ago
S$511
Return
found 3 days ago
Select Delta flight, departing Tue, 8 Jul from Los Angeles to Chicago, returning Wed, 9 Jul, priced at S$511 found 3 days ago
Delta
Mon, 7 Jul - Thu, 10 Jul
LAX
Los Angeles
MDW
Chicago
S$557 Return, found 2 hours ago
S$557
Return
found 2 hours ago
Select Delta flight, departing Mon, 7 Jul from Los Angeles to Chicago, returning Thu, 10 Jul, priced at S$557 found 2 hours ago
Delta
Thu, 11 Sep - Sat, 13 Sep
LAX
Los Angeles
MDW
Chicago
S$570 Return, found 3 days ago
S$570
Return
found 3 days ago
Select Delta flight, departing Thu, 11 Sep from Los Angeles to Chicago, returning Sat, 13 Sep, priced at S$570 found 3 days ago
Delta
Fri, 1 Aug - Fri, 8 Aug
LAX
Los Angeles
MDW
Chicago
S$583 Return, found 22 hours ago
S$583
Return
found 22 hours ago
Select Delta flight, departing Fri, 1 Aug from Los Angeles to Chicago, returning Fri, 8 Aug, priced at S$583 found 22 hours ago
Delta
Tue, 24 Jun - Thu, 26 Jun
LAX
Los Angeles
MDW
Chicago
S$599 Return, found 1 day ago
S$599
Return
found 1 day ago
Select Delta flight, departing Tue, 24 Jun from Los Angeles to Chicago, returning Thu, 26 Jun, priced at S$599 found 1 day ago

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

February is typically the cheapest month to fly

From S$152 - S$348 per traveller.

Graph displaying average flight prices per month

Los Angeles to Chicago route information
Origin airport
Los Angeles Intl.
Destination airport
Midway Intl.
Airlines serving
Delta
Return price
S$342
Distance
2795 km
Average flight time
6 hours 43 mins

Perfect flights from Los Angeles to Chicago

Your Journey from Los Angeles to Chicago

Start your unforgettable journey with Expedia. Our broad selection of flights from Los Angeles to Chicago caters to every travel need. Whether you're yearning for a romantic escape, a solo adventure, or a cultural immersion, we've got you covered.
 

Choosing Your Ideal Flight

With Expedia, you have access to a wide range of airlines, including Delta. Our selection of flights from Los Angeles Intl. to Midway Intl. caters to every traveler's requirements, ensuring your journey aligns with your schedule. With options from 20 airlines, you're bound to find the perfect flight.
 

Maximizing Value with Los Angeles to Chicago Flights

Experience the joy of finding cheap flights from Los Angeles Intl. to Midway Intl. that fit your budget. Keep an eye out for our special deals and discounts, and check our flexible one-way fares from S$165 and roundtrip prices from S$342*.
 

Pre-Flight Essentials

Ensure a smooth journey from Los Angeles to Chicago with Expedia. From information about check-in times and in-flight amenities to guidance on baggage policies, we provide all the essentials to prepare you for your flight.
 

Experience the Vibrant Chicago

Picture yourself stepping off the plane in Chicago and immersing yourself in the unique atmosphere of . From local markets to cultural festivals, each city offers its distinct charm. Make the most of your trip by exploring local attractions and indulging in the local cuisine. With Expedia, explore all this and more, tailored to your budget.
 

Added Convenience on Your Los Angeles to Chicago Flight

Traveling with Expedia is more than just a flight. We offer details about in-flight amenities, baggage policies, and more to ensure a smooth and hassle-free journey. Choose from our variety of airlines and embark on a memorable journey from Los Angeles to Chicago.
 

Beyond the Flight – Exploring Chicago

With Expedia, your adventure extends beyond the flight. Explore Chicago at your own pace by renting a car or booking a hotel. Discover hidden gems off the beaten path and create unforgettable memories.
 

Book Your Flight from Los Angeles to Chicago with Confidence

Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support make your travel experience seamless and stress-free. Embark on your journey from Los Angeles to Chicago with confidence. Book your travel arrangements with Expedia today.
 
*Note: Prices may vary based on availability and are subject to change.

Frequently asked questions

How much is a flight from Los Angeles Intl. Airport (LAX) to Midway Airport?
The lowest price advertised for a round-trip journey between LAX and Midway Intl. Airport (MDW) is S$342. But you better act fast. This price is based on fares available within the last 7 days on Expedia for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from LAX to Midway Airport?
The majority of flights can be cancelled online, but each airline has different terms and conditions. If you do have to cancel your flight, check out our Customer Service Portal and follow the instructions.
How do I find cheap flights from Los Angeles Intl. Airport (LAX) to Chicago Airport that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you're searching for LAX to Midway Intl. Airport (MDW) flights, you'll see a "no change fees" filter for you to select.
How far is the flight from LAX to Midway Intl. Airport (MDW)?
The flight distance between Los Angeles Intl. Airport (LAX) and Midway Intl. Airport (MDW) is 2,800 kilometres. Listen to your favourite tunes or read a good book and the trip will zip by.
Which airlines fly direct from Los Angeles Intl. Airport (LAX) to MDW?
If you want to fly straight from Los Angeles Intl. Airport (LAX) to Midway Airport, Southwest Airlines (WN) is a great option. It operates 104 flights every month between Los Angeles and Chicago.
Are LAX to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute?
Late planners can occasionally nab a bargain, with some of the cheapest fares from Los Angeles Intl. Airport (LAX) to Midway Airport arising a few weeks before the departure date. If you'd rather book ahead, Expedia compares and updates the best flight deals continually --- as early as a year in advance in some cases. It does depend on the carrier though, as not all airlines release prices so far in advance.

Explore a world of travel with Expedia

Chicago Airports

Chicago

Los Angeles to O'Hare Intl.
S$328.90
Los Angeles Airports

Orange County

*Available to Expedia members.