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Palm Springs

$126+ Cheap flights from Midway (MDW) to Palm Springs (PSP)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/25. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PSP
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Midway to Palm Springs

Cheapest flights from Midway to Palm Springs
Explore the most affordable flight options available from Midway to Palm Springs. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This Southwest deal was found by Cheapflights users on 1/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/148:15 am
MDW
-
PSP
Nonstop4h 20m
Southwest
Wed 2/188:55 am
PSP
-
MDW
1 stop6h 20m
Southwest
Deal found 1/23$299
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/289:40 pm
MDW
-
PSP
1 stop12h 50m
Southwest
Sat 4/46:35 pm
PSP
-
MDW
1 stop9h 00m
Southwest
Deal found 1/25$300
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/227:55 am
MDW
-
PSP
1 stop7h 55m
Southwest
Sat 2/287:20 am
PSP
-
MDW
2 stops7h 40m
Southwest
Deal found 1/24$304
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/74:35 pm
MDW
-
PSP
2 stops9h 20m
Southwest
Wed 3/119:00 pm
PSP
-
MDW
1 stop6h 55m
Southwest
Deal found 1/25$306
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:20 pm
MDW
-
PSP
2 stops7h 30m
Southwest
Wed 4/86:40 am
PSP
-
MDW
2 stops7h 55m
Southwest
Deal found 1/25$307
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:35 pm
MDW
-
PSP
1 stop6h 05m
Southwest
Fri 2/275:45 am
PSP
-
MDW
2 stops8h 30m
Southwest
Deal found 1/24$309
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:28 pm
MDW
-
PSP
2 stops10h 10m
Delta
Wed 2/2512:57 pm
PSP
-
MDW
1 stop7h 34m
Delta
Deal found 1/25$310
This Southwest deal was found by Cheapflights users on 1/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/143:15 pm
MDW
-
PSP
2 stops9h 20m
Southwest
Tue 2/176:30 am
PSP
-
MDW
1 stop5h 55m
Southwest
Deal found 1/24$315
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/152:55 pm
MDW
-
PSP
2 stops8h 55m
Southwest
Sat 4/186:05 am
PSP
-
MDW
2 stops9h 10m
Southwest
Deal found 1/25$317
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/59:30 am
MDW
-
PSP
1 stop6h 54m
Delta
Fri 4/1012:47 pm
PSP
-
MDW
1 stop7h 44m
Delta
Deal found 1/25$321
This Southwest deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1110:30 am
MDW
-
PSP
2 stops12h 55m
Southwest
Mon 3/168:40 pm
PSP
-
MDW
1 stop7h 15m
Southwest
Deal found 1/25$323

Find flight deals from Midway to Palm Springs

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Palm Springs (PSP). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$300
(Southwest)

One-way from

$126
(Delta)

Popular in

March

Cheapest in

January

Average price

$326
Provider with most accurate pricing for Chicago Midway-Palm Springs flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Palm Springs flights.
Search Deals
From Chicago Midway to Palm Springs
Search Deals
One-way flight from Chicago Midway to Palm Springs
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($36 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Palm Springs that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Palm Springs that are best for you.

Fly from

Midway

Fly to

Palm Springs

Route

Depart

Return

Price

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 3/28

9:40 pm-8:30 am

1 stop12h 50m

Palm Springs

Sat 4/4

6:35 pm-5:35 am

1 stop9h 00m

$300

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Wed 4/8

2:55 pm-9:50 pm

2 stops8h 55m

Palm Springs

Sat 4/11

6:50 am-7:20 pm

1 stop10h 30m

$309

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 4/7

6:00 am-11:36 am

1 stop7h 36m

Palm Springs

Wed 4/8

12:47 pm-10:31 pm

1 stop7h 44m

$321

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Fri 3/20

10:05 am-9:50 pm

1 stop13h 45m

Palm Springs

Tue 3/24

6:05 pm-5:45 am

1 stop9h 40m

$332

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 3/3

2:10 pm-8:50 pm

2 stops8h 40m

Palm Springs

Fri 3/6

6:35 am-1:50 pm

1 stop5h 15m

$339

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Fri 3/20

10:05 am-9:50 pm

1 stop13h 45m

Palm Springs

Mon 3/30

8:40 pm-5:55 am

1 stop7h 15m

$359

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 3/21

9:40 pm-8:30 am

1 stop12h 50m

Palm Springs

Sat 3/28

9:00 pm-5:55 am

1 stop6h 55m

$359

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 3/14

7:35 pm-11:50 pm

1 stop6h 15m

Palm Springs

Sun 3/22

8:00 pm-5:55 am

1 stop7h 55m

$379

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Mon 2/2

3:40 pm-8:50 pm

1 stop7h 10m

Palm Springs

Sat 2/7

11:55 am-8:30 pm

1 stop6h 35m

$388

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Wed 2/25

5:35 pm-9:40 pm

1 stop6h 05m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 16 results
1
2

Compare providers for flights from Midway to Palm Springs

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Palm Springs in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Palm Springs flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Palm Springs flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Palm Springs flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Palm Springs flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Palm Springs flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to Palm Springs

Have a flexible travel schedule? Discover the best time to fly to Palm Springs from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to Palm Springs

What is the cheapest month to book a flight from Chicago Midway Airport to Palm Springs?

Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Palm Springs (average of $130). Flying from Chicago Midway Airport to Palm Springs in June is currently the most expensive (average of $297). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Palm Springs

Get insights into the airlines that provide service to Palm Springs. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Palm Springs. Reviews last updated January 26, 2026.
See what other customers who have flown with Southwest from Chicago Midway Airport to Palm Springs have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Crew

8.6

Overall

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Midway to Palm Springs. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Palm Springs from Chicago Midway?

    Palm Springs (PSP), located 2.2 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to Palm Springs. 1 airline have flights to Palm Springs from Chicago Midway on a regular basis. Booking flights from Chicago Midway to Palm Springs should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to Palm Springs?

    Departing from Chicago Midway Airport to Palm Springs will take you 7h 36m. Airlines will cover a distance of 1653 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from Chicago Midway Airport to Palm Springs round-trip?

    According to our current data, Southwest ($282), offers the cheapest pricing from Chicago Midway Airport to Palm Springs. This flight start at 32% lower than the current average price 3 months from now.

  • Can I find deals for flights from Midway to Palm Springs that include hotel bookings?

    Yes. In addition to deals on Midway to Palm Springs flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Palm Springs?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Palm Springs.

  • Can I find deals for business class flights from Midway to Palm Springs?

    Yes. Cheapflights offers flight deals from Midway to Palm Springs by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, March is the cheapest month in which you can book a flight from Chicago Midway Airport to Palm Springs (average of $130). Flying from Chicago Midway Airport to Palm Springs in June is currently the most expensive (average of $297). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Palm Springs?

Book flights to Palm Springs if you plan to visit one of these locations
Indio
La Quinta
Cabazon
Rancho Mirage
Cathedral City
Indian Wells
Banning
Desert Hot Springs
Yucca Valley
Coachella

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Top airline flying from Midway to Palm Springs

Discover the top airline that operate flights from Midway to Palm Springs. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$282Average$489FlexibilityNo cancel feeOn-time63%

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