MDW - PSP

$141 Find Cheap Flights from Chicago Midway Airport to Palm Springs - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to Palm Springs departing on 9/30. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$281
Typical prices: $320-$520
Southwest
Tue 10/6Wed 10/7
MDW - PSP • 1 stop
Cheapest one-way
$141
Southwest
Wed 9/30
MDW - PSP • 1 stop
Top airlines
Cheapest • from $281 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top layover airports
Cheapest • Avg $430 (round-trip)
Shortest trip • 6h 15m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
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 Palm Springs!
Flight Deals
Booking Insights
Flight Deals

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

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

Tue, Oct 6 - Wed, Oct 7
Southwest Logo
6:05 am - 10:15 am
MDW
-
PSP
6h 10m
1 stop
Southwest Logo
10:55 am - 9:00 pm
PSP
-
MDW
8h 05m
1 stop
$281Southwest
Sat, Sep 5 - Fri, Sep 11
Southwest Logo
5:05 pm - 9:00 pm
MDW
-
PSP
5h 55m
1 stop
Southwest Logo
4:00 pm - 12:30 am
PSP
-
MDW
6h 30m
1 stop
$281Southwest
Tue, Jan 5 - Sat, Jan 9
Delta Logo
6:00 am - 11:23 am
MDW
-
PSP
7h 23m
1 stop
Delta Logo
12:40 pm - 10:10 pm
PSP
-
MDW
7h 30m
1 stop
$281Delta
Sat, Dec 5 - Sat, Dec 12
Delta Logo
6:00 am - 11:27 am
MDW
-
PSP
7h 27m
1 stop
Delta Logo
12:37 pm - 10:56 pm
PSP
-
MDW
8h 19m
1 stop
$281Delta
Sat, Jan 9 - Sat, Jan 16
Delta Logo
6:00 am - 11:23 am
MDW
-
PSP
7h 23m
1 stop
Delta Logo
12:40 pm - 10:10 pm
PSP
-
MDW
7h 30m
1 stop
$281Delta
Tue, Oct 13 - Wed, Oct 14
Southwest Logo
6:05 am - 10:15 am
MDW
-
PSP
6h 10m
1 stop
Southwest Logo
12:05 pm - 9:00 pm
PSP
-
MDW
6h 55m
1 stop
$281Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
6:05 am - 10:10 am
MDW
-
PSP
6h 05m
1 stop
Southwest Logo
6:00 am - 1:25 pm
PSP
-
MDW
5h 25m
1 stop
$281Southwest
Sat, Oct 24 - Tue, Oct 27
Southwest Logo
5:05 pm - 9:00 pm
MDW
-
PSP
5h 55m
1 stop
Southwest Logo
10:55 am - 9:00 pm
PSP
-
MDW
8h 05m
1 stop
$281Southwest
Sat, Jan 9 - Sat, Jan 16
Delta Logo
9:55 am - 4:27 pm
MDW
-
PSP
8h 32m
2 stops
Delta Logo
12:40 pm - 10:10 pm
PSP
-
MDW
7h 30m
1 stop
$286Delta
Tue, Oct 20 - Sat, Oct 24
Southwest Logo
6:05 am - 10:15 am
MDW
-
PSP
6h 10m
1 stop
Southwest Logo
3:45 pm - 4:30 am
PSP
-
MDW
10h 45m
2 stops
$286Southwest
Booking Insights

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago Midway Airport to Palm Springs, 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 Chicago Midway Airport to Palm Springs is July, where tickets cost $0 (return) on average. On the other hand, the most expensive months are March and August, where the average cost of round-trip tickets is $611 and $578 respectively.

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

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 1 stop layover the cheapest option at $533 on average.

Good to know

Low season

December

Cheapest flight

$141
Best time to beat the crowds with an average 41% drop in price.
Most popular time to fly and prices are also 25% lower on average.
Flight from Chicago Midway Airport to Palm Springs

When to book flights from Midway to Palm Springs

Are your dates flexible? Find out the best times to travel from Midway to Palm Springs 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 Chicago Midway Airport to Palm Springs flights

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

    In the last 5 days, the lowest price for a flight from Chicago Midway Airport to Palm Springs was $141 for a one-way ticket and $281 for a round-trip.

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

    No, a passport isn't needed to fly from Chicago Midway Airport to Palm Springs. However, local authorities might ask for an official ID.

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

    Only American Airlines offers inflight Wi-Fi service on the Chicago Midway Airport to Palm Springs flight route.

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

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago Midway Airport to Palm Springs flight route.

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

    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 Chicago Midway Airport to Palm Springs.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Palm Springs from Chicago Midway Airport 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 Chicago Midway Airport to Palm Springs?

    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 Palm Springs with an airline and back to Chicago Midway Airport with another airline. Booking your flights between Chicago Midway Airport and PSP 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 Chicago Midway Airport to Palm Springs?

    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 Palm Springs from Chicago Midway Airport 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 Midway to Palm Springs

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Palm Springs. 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 Midway to Palm Springs? 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 4229 reviews
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

Flight had over 6 people in wheel chairs and there was only 1 gate agent. Very impressed though in how Maddie handled having to efficiency move that many people by herself. We still nursed in a timely manner.

no entertainment options available on a 4+ hour flight. packed in like sardines. one bathroom. late flight.

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

Information on your arrival and departure airports