PSP - MDW

$136 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 5/29. 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

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$276
Typical prices: $645-$426
Southwest
Wed 10/7Tue 10/13
PSP - MDW • 1 stop
Cheapest one-way
$136
Typical prices: $160-$243
Southwest
Fri 5/29
PSP - MDW • 1 stop
Top airlines
Southwest
Cheapest • from $276 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Denver (DEN)
Cheapest • Avg $327 (round-trip)
Atlanta (ATL)
Shortest trip • 6h 38m (one-way)
Insights
Insights
Insights
Insights
When to travel
March
Cheapest • 100% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
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

Wed, Oct 7 - Tue, Oct 13
Southwest Logo
1:55 pm - 9:50 pm
PSP
-
MDW
5h 55m
1 stop
Southwest Logo
7:00 am - 1:20 pm
MDW
-
PSP
8h 20m
2 stops
$276Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
2:35 pm - 10:00 pm
PSP
-
MDW
5h 25m
1 stop
Southwest Logo
10:15 am - 5:30 pm
MDW
-
PSP
9h 15m
2 stops
$314Southwest
Tue, Jun 2 - Sat, Jun 6
Southwest Logo
6:10 am - 4:55 pm
PSP
-
MDW
8h 45m
2 stops
Southwest Logo
10:15 am - 5:30 pm
MDW
-
PSP
9h 15m
2 stops
$319Southwest
Thu, Jul 16 - Sat, Jul 18
Delta Logo
5:15 pm - 9:08 am
PSP
-
MDW
13h 53m
2 stops
Delta Logo
9:49 am - 4:38 pm
MDW
-
PSP
8h 49m
2 stops
$320Delta
Tue, Jun 16 - Sat, Jun 27
Southwest Logo
6:30 pm - 5:25 am
PSP
-
MDW
8h 55m
2 stops
Southwest Logo
10:15 am - 5:30 pm
MDW
-
PSP
9h 15m
2 stops
$339Southwest
Sat, Oct 3 - Wed, Oct 7
Southwest Logo
3:30 pm - 5:40 am
PSP
-
MDW
12h 10m
1 stop
Southwest Logo
7:00 am - 1:20 pm
MDW
-
PSP
8h 20m
2 stops
$340Southwest
Tue, Jun 2 - Tue, Jun 9
Southwest Logo
2:35 pm - 10:00 pm
PSP
-
MDW
5h 25m
1 stop
Southwest Logo
4:40 pm - 10:05 pm
MDW
-
PSP
7h 25m
1 stop
$344Southwest
Tue, May 19 - Sat, May 23
Southwest Logo
2:35 pm - 10:00 pm
PSP
-
MDW
5h 25m
1 stop
Southwest Logo
5:30 pm - 9:10 pm
MDW
-
PSP
5h 40m
1 stop
$347Southwest
Thu, Jun 11 - Tue, Jun 23
Southwest Logo
4:10 pm - 1:25 am
PSP
-
MDW
7h 15m
1 stop
Southwest Logo
6:00 pm - 10:05 pm
MDW
-
PSP
6h 05m
1 stop
$348Southwest
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
10:20 am - 8:00 pm
PSP
-
MDW
7h 40m
2 stops
Southwest Logo
4:40 pm - 10:05 pm
MDW
-
PSP
7h 25m
1 stop
$349Southwest
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.

How much is a round-trip flight from Palm Springs to Chicago Midway Airport?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Palm Springs to Chicago Midway Airport departing in October.

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 March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $725 and $535 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.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $305 on average.

Find deals

Good to know

Low seasonJuly
Cheapest flight$136
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly and prices are also 36% 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 $136 for a one-way ticket and $276 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.

  • 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.

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.
7.9
SouthwestOverall score based on 4301 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

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)