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$155+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — PSP
Apr 12 — Apr 191
Sun 4/12
Sun 4/19
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 March 13, 2026.

This Southwest deal was found by Cheapflights users on 3/10. 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 4/74:40 pm
MDW
-
PSP
2 stops7h 10m
Southwest
Wed 4/156:10 am
PSP
-
MDW
2 stops8h 50m
Southwest
Deal found 3/10$290
This Southwest deal was found by Cheapflights users on 3/8. 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 4/158:50 pm
MDW
-
PSP
1 stop13h 40m
Southwest
Wed 4/226:40 am
PSP
-
MDW
2 stops7h 55m
Southwest
Deal found 3/8$291
This Southwest deal was found by Cheapflights users on 3/10. 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 4/226:30 am
MDW
-
PSP
1 stop5h 45m
Southwest
Thu 4/235:30 am
PSP
-
MDW
2 stops7h 45m
Southwest
Deal found 3/10$295
This Southwest deal was found by Cheapflights users on 3/8. 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 6/65:10 pm
MDW
-
PSP
1 stop7h 35m
Southwest
Wed 6/106:15 am
PSP
-
MDW
1 stop5h 35m
Southwest
Deal found 3/8$296
This Delta deal was found by Cheapflights users on 3/10. 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.
Fri 4/109:30 am
MDW
-
PSP
1 stop6h 54m
Delta
Sat 4/181:27 pm
PSP
-
MDW
1 stop7h 01m
Delta
Deal found 3/10$300
This Southwest deal was found by Cheapflights users on 3/9. 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 5/232:40 pm
MDW
-
PSP
1 stop6h 20m
Southwest
Tue 5/266:25 pm
PSP
-
MDW
1 stop9h 20m
Southwest
Deal found 3/9$304
This Southwest deal was found by Cheapflights users on 3/10. 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.
Mon 4/2010:20 am
MDW
-
PSP
2 stops8h 35m
Southwest
Tue 4/216:25 pm
PSP
-
MDW
1 stop9h 20m
Southwest
Deal found 3/10$305
This Southwest deal was found by Cheapflights users on 3/10. 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 4/57:10 am
MDW
-
PSP
1 stop6h 25m
Southwest
Fri 4/103:05 pm
PSP
-
MDW
1 stop6h 35m
Southwest
Deal found 3/10$309
This Southwest deal was found by Cheapflights users on 3/11. 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 4/87:40 am
MDW
-
PSP
2 stops8h 15m
Southwest
Tue 4/146:10 am
PSP
-
MDW
2 stops8h 50m
Southwest
Deal found 3/11$310
This Southwest deal was found by Cheapflights users on 3/11. 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.
Thu 4/309:50 pm
MDW
-
PSP
1 stop12h 40m
Southwest
Tue 5/56:40 am
PSP
-
MDW
2 stops7h 55m
Southwest
Deal found 3/11$311

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 March 13, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Southwest)

One-way from

$155
(Southwest)

Popular in

March

Cheapest in

January

Average price

$695
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. 21% potential increase in price ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 13, 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
Quickest round-trip

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 6/6

4:50 pm-10:45 pm

2 stops7h 55m

Palm Springs

Wed 6/10

6:15 am-1:50 pm

1 stop5h 35m

$301

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Mon 4/27

6:00 am-9:50 am

1 stop5h 50m

Palm Springs

Sat 5/2

5:40 am-5:30 pm

2 stops9h 50m

$305

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sun 4/26

7:20 pm-11:50 pm

1 stop6h 30m

Palm Springs

Fri 5/1

6:50 pm-5:25 am

2 stops8h 35m

$334

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Sat 5/30

9:22 am-4:28 pm

2 stops9h 06m

Palm Springs

Wed 6/3

6:05 am-6:33 pm

2 stops10h 28m

$399

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Fri 4/3

9:30 am-2:24 pm

1 stop6h 54m

Palm Springs

Thu 4/9

12:47 pm-10:31 pm

1 stop7h 44m

$418

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Thu 4/16

9:50 pm-8:30 am

1 stop12h 40m

Palm Springs

Sat 4/18

6:50 am-2:35 pm

1 stop5h 45m

$465

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Wed 5/13

2:10 pm-9:30 pm

2 stops9h 20m

Palm Springs

Sun 5/17

7:55 pm-6:00 am

1 stop8h 05m

$491

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Mon 5/18

1:22 pm-9:17 pm

2 stops9h 55m

Palm Springs

Sun 5/24

6:05 am-6:33 pm

2 stops10h 28m

$499

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Thu 6/11

10:10 am-3:35 pm

1 stop7h 25m

Palm Springs

Sun 6/14

6:35 pm-5:10 am

2 stops8h 35m

$514

ChicagoPalm Springs

MDW - PSP

MDWPSP

Chicago Midway

Fri 4/24

10:05 am-5:35 pm

2 stops9h 30m

Palm Springs

Sun 4/26

7:55 pm-6:00 am

1 stop8h 05m

$558

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 March.
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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Palm Springs (average of $153). Flying from Chicago Midway Airport to Palm Springs in June is currently the most expensive (average of $294). 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 March 13, 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
4,319 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
4,319 reviews
Southwest
8.0
Very good
4,319 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

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 55m. 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 ($254), offers the cheapest pricing from Chicago Midway Airport to Palm Springs. This flight start at 43% 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to Palm Springs (average of $153). Flying from Chicago Midway Airport to Palm Springs in June is currently the most expensive (average of $294). 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
Rancho Mirage
Desert Hot Springs
Cathedral City
Indian Wells
Yucca Valley
Banning
Cabazon
Coachella

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$254Average$513FlexibilityNo cancel feeOn-time63%

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