$80 Cheap Flights from Palm Springs (PSP) to Chicago (MDW)

View $80 flight on Tue, Oct 28, 2025Opens in a new window

Popular airlines from Palm Springs Intl. Airport (PSP) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at $80 for one-way flights and $187 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Nov 7 - Tue, Nov 11
PSP
Palm Springs
MDW
Chicago
$187 Roundtrip, found 5 days ago
$187
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Fri, Nov 7 from Palm Springs to Chicago, returning Tue, Nov 11, priced at $187 found 5 days ago
Southwest Airlines
Thu, Oct 23 - Tue, Oct 28
PSP
Palm Springs
MDW
Chicago
$189 Roundtrip, found 5 days ago
$189
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Palm Springs to Chicago, returning Tue, Oct 28, priced at $189 found 5 days ago
Southwest Airlines
Mon, Oct 27 - Wed, Oct 29
PSP
Palm Springs
MDW
Chicago
$194 Roundtrip, found 5 days ago
$194
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Palm Springs to Chicago, returning Wed, Oct 29, priced at $194 found 5 days ago
Southwest Airlines
Thu, Oct 23 - Tue, Oct 28
PSP
Palm Springs
MDW
Chicago
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Palm Springs to Chicago, returning Tue, Oct 28, priced at $203 found 5 days ago
Southwest Airlines
Thu, Oct 23 - Tue, Oct 28
PSP
Palm Springs
MDW
Chicago
$208 Roundtrip, found 5 days ago
$208
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Palm Springs to Chicago, returning Tue, Oct 28, priced at $208 found 5 days ago
Southwest Airlines
Mon, Oct 27 - Wed, Oct 29
PSP
Palm Springs
MDW
Chicago
$209 Roundtrip, found 5 days ago
$209
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Palm Springs to Chicago, returning Wed, Oct 29, priced at $209 found 5 days ago
Delta
Fri, Nov 7 - Tue, Nov 11
PSP
Palm Springs
MDW
Chicago
$211 Roundtrip, found 5 days ago
$211
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Nov 7 from Palm Springs to Chicago, returning Tue, Nov 11, priced at $211 found 5 days ago
Southwest Airlines
Wed, Oct 29 - Sun, Nov 2
PSP
Palm Springs
MDW
Chicago
$212 Roundtrip, found 6 days ago
$212
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Palm Springs to Chicago, returning Sun, Nov 2, priced at $212 found 6 days ago
Southwest Airlines
Wed, Oct 15 - Tue, Oct 21
PSP
Palm Springs
MDW
Chicago
$219 Roundtrip, found 6 days ago
$219
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 15 from Palm Springs to Chicago, returning Tue, Oct 21, priced at $219 found 6 days ago
Frontier Airlines
Fri, Oct 17 - Thu, Oct 23
PSP
Palm Springs
MDW
Chicago
$326 Roundtrip, found 13 hours ago
$326
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Fri, Oct 17 from Palm Springs to Chicago, returning Thu, Oct 23, priced at $326 found 13 hours ago

Find the cheapest month to fly from Palm Springs (PSP) to Chicago (MDW)

February is typically the cheapest month to fly

From $134 - $628 per traveler.

Frequently asked questions

How much does a flight from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW) cost?
Grab a cheap one-way flight from $80 or cheap return flight from $187 from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)?
November is the least expensive month to fly from PSP to MDW. Timing your trip outside of the busy season is often the key to landing a great deal.
What is the cheapest airline that flies from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from PSP to MDW, use Expedia's filter tool. Tailor your search based on what matters most to you, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)?
There are no daily nonstop flights available from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way before you know it.
What day of the week has the most flights from PSP to MDW?
Friday is generally the busiest day for flights, while Tuesday is often the quietest.* Keep in mind that flight schedules can change based on a number of factors, such as the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)?
Select a flight from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW) that leaves before 3 PM to reduce the likelihood of delays. Later departures are on average 22% more likely to be canceled.**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 Palm Springs Intl. Airport (PSP)?
If you've booked a direct flight from Palm Springs Intl. Airport (PSP) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW) last-minute?
Booking your ticket from PSP to MDW right before your trip is generally more expensive. However, if you're flexible with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book a PSP to MDW flight and hotel package?
Booking a PSP to MDW flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)?
If you reserved your PSP to MDW flight within the last 24 hours, you may be able to cancel or modify it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you want more information.

Travel information

Travel information

Origin airport
Palm Springs Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$187
Distance
1654 mi

Book with confidence

Book with confidence

Palm Springs to Chicago Flights

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

 

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

Sunday is one of the best days to book for cheap flights from Palm Springs 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 Palm Springs 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 Palm Springs to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $80 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 Palm Springs 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 Palm Springs 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.

 

Palm Springs to Chicago Flights

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to One Key members.