$126 Cheap Flights from Chicago (MDW) to Palm Springs (PSP)

View $126 flight on Tue, Jun 17, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Chicago to Palm Springs (MDW-PSP)

Prices were available within the past 7 days and start at $126 for one-way flights and $262 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Wed, Jun 11 - Sat, Jun 14
MDW
Chicago
PSP
Palm Springs
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jun 11 from Chicago to Palm Springs, returning Sat, Jun 14, priced at $262 found 2 days ago
Delta
Sat, Jun 21 - Tue, Jun 24
MDW
Chicago
PSP
Palm Springs
$267 Roundtrip, found 1 hour ago
$267
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jun 21 from Chicago to Palm Springs, returning Tue, Jun 24, priced at $267 found 1 hour ago
Southwest Airlines
Wed, Jun 4 - Fri, Jun 6
MDW
Chicago
PSP
Palm Springs
$270 Roundtrip, found 6 hours ago
$270
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Jun 4 from Chicago to Palm Springs, returning Fri, Jun 6, priced at $270 found 6 hours ago
Southwest Airlines
Wed, Jun 4 - Fri, Jun 6
MDW
Chicago
PSP
Palm Springs
$275 Roundtrip, found 6 hours ago
$275
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Jun 4 from Chicago to Palm Springs, returning Fri, Jun 6, priced at $275 found 6 hours ago
Southwest Airlines
Wed, Jun 11 - Sat, Jun 14
MDW
Chicago
PSP
Palm Springs
$282 Roundtrip, found 2 days ago
$282
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Jun 11 from Chicago to Palm Springs, returning Sat, Jun 14, priced at $282 found 2 days ago
Delta
Sat, Jun 21 - Tue, Jun 24
MDW
Chicago
PSP
Palm Springs
$283 Roundtrip, found 1 hour ago
$283
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Jun 21 from Chicago to Palm Springs, returning Tue, Jun 24, priced at $283 found 1 hour ago
Southwest Airlines
Tue, May 13 - Fri, May 16
MDW
Chicago
PSP
Palm Springs
$289 Roundtrip, found 1 day ago
$289
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, May 13 from Chicago to Palm Springs, returning Fri, May 16, priced at $289 found 1 day ago
Southwest Airlines
Tue, May 13 - Tue, May 20
MDW
Chicago
PSP
Palm Springs
$294 Roundtrip, found 2 days ago
$294
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, May 13 from Chicago to Palm Springs, returning Tue, May 20, priced at $294 found 2 days ago
Southwest Airlines
Fri, Jun 20 - Wed, Jun 25
MDW
Chicago
PSP
Palm Springs
$294 Roundtrip, found 1 day ago
$294
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Jun 20 from Chicago to Palm Springs, returning Wed, Jun 25, priced at $294 found 1 day ago
Southwest Airlines
Tue, Jul 1 - Sat, Jul 5
MDW
Chicago
PSP
Palm Springs
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Tue, Jul 1 from Chicago to Palm Springs, returning Sat, Jul 5, priced at $297 found 2 days ago
Flights from Chicago (MDW) to Palm Springs (PSP)
Origin airport
Midway Intl.
Destination airport
Palm Springs Intl.
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$262
Distance
1654 mi

Chicago to Palm Springs Flights

The cheapest times to fly from Chicago to Palm Springs

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 Chicago to Palm Springs are during the month of June. You can find some of the cheapest flights from Chicago to Palm Springs with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Palm Springs

Sunday is one of the best days to book for cheap flights from Chicago to Palm Springs: 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 Chicago to Palm Springs

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 Chicago to Palm Springs in 2025. You can also book with separate airlines for your outbound and return journeys, from $126 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 Chicago to Palm Springs 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 Chicago to Palm Springs 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 Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP) cost?
Discover the latest flight deals from MDW to PSP by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from MDW to PSP?
The cheapest flights from MDW to PSP are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP)?
While Chicago, IL (MDW-Midway Intl.) has no direct flights to Palm Springs Intl. Airport (PSP), other airports have nonstop options. Flying from O’Hare Intl. Airport (ORD) will get you to Palm Springs without any layovers.
What is the cheapest airline that flies from MDW to PSP?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from MDW to PSP. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP)?
Direct flights from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP) aren’t available daily, so you’ll need to take a flight with a layover. Explore your options with Expedia’s filters. Enter your travel dates and select either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from MDW to PSP?
Usually you’ll find the greatest selection of flight options on a Friday. Tuesdays tend to be the quietest.* But this can vary depending on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP)?
To arrive at Palm Springs Intl. Airport (PSP) on time, book a flight that leaves from Midway Intl. Airport (MDW) before 3 PM. The likelihood of cancellations is 22% higher, on average, for departures after this hour.**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.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP) last-minute?
Booking your plane ticket from MDW to PSP right before your journey is usually more expensive. However, if there’s some wiggle room with your itinerary, you could grab a cheap last-minute fare.
Is it cheaper to book a MDW to PSP flight and hotel package?
Compared with arranging hotels and flights separately, booking a MDW to PSP flight and hotel package with Expedia could lead to significant savings. Better yet, having everything in one convenient place will take the stress out of travel planning. Just pick your flights and select from our wide range of stays, then customize your trip with extras like activities and car rentals.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Palm Springs Intl. Airport (PSP)?
In most instances, you can modify or cancel your MDW to PSP flight. However, there may be additional fees, especially if your booking was made over 24 hours ago. Check your itinerary for the airline’s fees and guidelines on flight changes, or if you want further details, head to our Customer Service portal.

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*Available to One Key members.