PSP - MDW

$165 Find Cheap Flights from Palm Springs to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Palm Springs to Midway departing on 4/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$266
Overall average: $326
Southwest
Sat 4/18Sat 4/25
PSP - MDW • 1 stop
Cheapest one-way
$165
Typical prices: $282-$343
Southwest
Thu 4/30
PSP - MDW • 1 stop
Nonstop flights
1 day a week
Sat
You can fly direct with Southwest. Average duration is 3h 35m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top airlines
Southwest
Cheapest • from $266 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Denver (DEN)
Cheapest • Avg $309 (round-trip)
Las Vegas (LAS)
Shortest trip • 6h 32m (one-way)
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 37% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Palm Springs to Midway 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.

Recent round-trip flight deals from Palm Springs to Midway

Sat, Apr 18 - Sat, Apr 25
Southwest Logo
2:35 pm - 11:05 pm
PSP
-
MDW
6h 30m
1 stop
Southwest Logo
2:30 pm - 7:00 pm
MDW
-
PSP
6h 30m
1 stop
$266Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
2:35 pm - 11:05 pm
PSP
-
MDW
6h 30m
1 stop
Southwest Logo
6:30 am - 10:15 am
MDW
-
PSP
5h 45m
1 stop
$271Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
6:05 am - 5:15 pm
PSP
-
MDW
9h 10m
2 stops
Southwest Logo
2:30 pm - 7:00 pm
MDW
-
PSP
6h 30m
1 stop
$272Southwest
Sat, Apr 18 - Tue, Apr 21
Southwest Logo
6:05 am - 5:30 pm
PSP
-
MDW
9h 25m
2 stops
Southwest Logo
6:30 am - 10:15 am
MDW
-
PSP
5h 45m
1 stop
$276Southwest
Sat, Apr 18 - Sat, Apr 25
Southwest Logo
6:05 am - 5:15 pm
PSP
-
MDW
9h 10m
2 stops
Southwest Logo
5:10 am - 1:00 pm
MDW
-
PSP
9h 50m
2 stops
$281Southwest
Sat, May 16 - Tue, May 19
Southwest Logo
6:50 am - 7:20 pm
PSP
-
MDW
10h 30m
1 stop
Southwest Logo
7:30 am - 1:55 pm
MDW
-
PSP
8h 25m
2 stops
$282Southwest
Wed, Apr 15 - Sat, Apr 18
Delta Logo
1:27 pm - 10:28 pm
PSP
-
MDW
7h 01m
1 stop
Delta Logo
6:00 am - 12:16 pm
MDW
-
PSP
8h 16m
1 stop
$291Delta
Thu, Apr 23 - Sat, Apr 25
Southwest Logo
3:05 pm - 11:40 pm
PSP
-
MDW
6h 35m
1 stop
Southwest Logo
2:30 pm - 7:00 pm
MDW
-
PSP
6h 30m
1 stop
$295Southwest
Wed, Apr 15 - Tue, Apr 21
Delta Logo
1:27 pm - 10:28 pm
PSP
-
MDW
7h 01m
1 stop
Delta Logo
9:29 am - 9:27 pm
MDW
-
PSP
13h 58m
2 stops
$296Delta
Tue, Apr 28 - Sun, May 3
Southwest Logo
6:10 am - 2:10 pm
PSP
-
MDW
6h 00m
1 stop
Southwest Logo
7:20 pm - 11:50 pm
MDW
-
PSP
6h 30m
1 stop
$300Southwest
Booking Insights

KAYAK's insights & trends for Palm Springs to Midway flights

Get data-powered insights and trends into flights from Palm Springs to Midway to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Palm Springs to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Palm Springs to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Palm Springs to Chicago Midway Airport is July, where tickets cost $288 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $725 and $567 respectively.

Can I save money by flying with a layover from Palm Springs to Chicago Midway Airport?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $428, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$165
Best time to beat the crowds but there is an average 6% increase in price.
Most popular time to fly and prices are also 37% lower on average.
Flight from Palm Springs to Chicago Midway Airport

When to book flights from Palm Springs to Midway

Are your dates flexible? Find out the best times to travel from Palm Springs to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Palm Springs to Chicago Midway Airport flights

  • What is the cheapest flight from Palm Springs to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Palm Springs to Chicago Midway Airport was $165 for a one-way ticket and $266 for a round-trip.

  • Do I need a passport to fly between Palm Springs and Chicago Midway Airport?

    No

  • Which airlines offer Wi-Fi service onboard planes from Palm Springs to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Palm Springs to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Palm Springs to Chicago Midway Airport?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Palm Springs to Chicago Midway Airport flight route.

  • On which days can I fly direct from Palm Springs to Chicago Midway Airport?

    You can catch a nonstop flight from Palm Springs to Chicago Midway Airport on Saturday.

  • How does KAYAK find such low prices on flights from Palm Springs to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Palm Springs to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Palm Springs to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Palm Springs is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Palm Springs to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Palm Springs with another airline. Booking your flights between Palm Springs and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Palm Springs to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Palm Springs up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Palm Springs to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $510 or less one-way.

Prefer to fly direct from Palm Springs to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Palm Springs to Chicago Midway.
Find which airlines fly direct from Palm Springs Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Palm Springs to Chicago Midway

Saturday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Palm Springs

Saturday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Palm Springs to Midway

 
See real verified KAYAK customer reviews for airlines flying from Palm Springs to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Palm Springs to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4320 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
Airline reviews

Boarding was easy. The seats are small and fairly uncomfortable

8.0 ExcellentNicole, Mar 2026
LGB - OAK
Read more Southwest reviews

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything you need to know for your flight from Palm Springs to Midway

Information on your arrival and departure airports

Palm Springs (PSP)
Midway (MDW)