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$136+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PSP
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
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 July 25, 2026.

This Southwest deal was found by Cheapflights users on 7/20. 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 8/263:50 pm
MDW
-
PSP
1 stop8h 05m
Southwest
Mon 8/314:00 pm
PSP
-
MDW
1 stop6h 25m
Southwest
Deal found 7/20$274
This Southwest deal was found by Cheapflights users on 7/21. 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 12/510:20 am
MDW
-
PSP
1 stop6h 45m
Southwest
Wed 12/911:05 am
PSP
-
MDW
1 stop11h 00m
Southwest
Deal found 7/21$276
This Southwest deal was found by Cheapflights users on 7/21. 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 10/146:05 am
MDW
-
PSP
1 stop6h 05m
Southwest
Wed 10/1412:05 pm
PSP
-
MDW
1 stop8h 05m
Southwest
Deal found 7/21$277
This Southwest deal was found by Cheapflights users on 7/21. 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 12/510:20 am
MDW
-
PSP
1 stop6h 45m
Southwest
Thu 12/1011:05 am
PSP
-
MDW
2 stops8h 45m
Southwest
Deal found 7/21$279
This Southwest deal was found by Cheapflights users on 7/24. 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 9/86:00 pm
MDW
-
PSP
1 stop6h 00m
Southwest
Tue 9/157:05 am
PSP
-
MDW
1 stop5h 15m
Southwest
Deal found 7/24$281
This Southwest deal was found by Cheapflights users on 7/23. 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 9/125:05 pm
MDW
-
PSP
1 stop5h 55m
Southwest
Tue 9/155:30 pm
PSP
-
MDW
2 stops10h 10m
Southwest
Deal found 7/23$282
This Southwest deal was found by Cheapflights users on 7/22. 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 10/176:35 am
MDW
-
PSP
2 stops10h 25m
Southwest
Sat 10/243:45 pm
PSP
-
MDW
2 stops10h 45m
Southwest
Deal found 7/22$287
This Southwest deal was found by Cheapflights users on 7/22. 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 9/55:05 pm
MDW
-
PSP
1 stop5h 50m
Southwest
Sat 9/1211:20 am
PSP
-
MDW
2 stops15h 40m
Southwest
Deal found 7/22$288

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$274
(Southwest)

One-way from

$136
(Southwest)

Popular in

March

Cheapest in

December

Average price

$553
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. 10% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 25, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Palm Springs that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Wed 8/19

6:00 pm-9:55 pm

1 stop5h 55m

Palm Springs

Tue 8/25

7:05 am-7:15 pm

2 stops10h 10m

$276

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 10/20

6:05 am-10:10 am

1 stop6h 05m

Palm Springs

Tue 10/27

6:00 am-1:25 pm

1 stop5h 25m

$277
Quickest round-trip

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 9/8

6:00 pm-10:00 pm

1 stop6h 00m

Palm Springs

Tue 9/15

7:05 am-2:20 pm

1 stop5h 15m

$281

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 9/5

5:05 pm-8:55 pm

1 stop5h 50m

Palm Springs

Sat 9/12

7:20 am-7:10 pm

2 stops9h 50m

$282

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 9/15

3:50 pm-10:00 pm

1 stop8h 10m

Palm Springs

Tue 9/22

5:30 pm-5:45 am

1 stop10h 15m

$282

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Thu 10/22

9:50 am-6:30 pm

1 stop10h 40m

Palm Springs

Mon 10/26

7:05 pm-5:50 am

1 stop8h 45m

$282

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Mon 8/31

3:20 pm-10:10 pm

2 stops8h 50m

Palm Springs

Wed 9/2

11:05 am-10:50 pm

2 stops9h 45m

$303

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Tue 9/22

3:50 pm-10:00 pm

1 stop8h 10m

Palm Springs

Sat 9/26

11:20 am-7:35 pm

1 stop6h 15m

$318
Cheapest one-way

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Wed 8/19

3:50 pm-9:55 pm

1 stop8h 05m

$136
Quickest one-way

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 9/19

5:05 pm-8:55 pm

1 stop5h 50m

$136

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

Showing 1-10 of 17 resultsSorted by cheapest first
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 July.
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.

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 July 25, 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
4,233 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.
Southwest
8.0
Very good
4,233 reviews
Southwest
8.0
Very good
4,233 reviews

Food

7.0

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

Sarah,Aug 2024

MDW - AUS

My first time, surprisingly good! It was a good ride overall. Coming from Singapore, this budget flight is better than the budget airline for our national carrier Singapore Airlines.

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 5h 55m. Airlines will cover a distance of 1653 mi.

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

    According to our current data, Southwest ($273), offers the cheapest pricing from Chicago Midway Airport to Palm Springs. This flight start at 39% 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.

See more FAQs

Traveling to a place near Palm Springs?

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

Browse thousands of different options on Cheapflights for your next trip

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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 July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$273Average$520FlexibilityNo cancel feeOn-time63%

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