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$84+ Cheap flights from Palm Springs (PSP) to Midway (MDW)

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 10/20. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Palm Springs to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Palm Springs (PSP) to Midway (MDW). 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 September 17, 2025.

Round-trip from

$269
(Southwest)

One-way from

$84
(Trip.com)

Popular in

September

Cheapest in

July

Average price

$564
From Palm Springs to Chicago Midway
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One-way flight from Palm Springs to Chicago Midway
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Highest demand for flights based on searches. 9% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Palm Springs to Midway

Cheapest flights from Palm Springs to Midway
Explore the most affordable flight options available from Palm Springs to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Southwest deal was found by Cheapflights users on 9/17. 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 10/213:10 pmPSP - MDW
1 stop5h 30mSouthwest
Tue 10/288:00 amMDW - PSP
1 stop6h 25mSouthwest
Deal found 9/17$269
This Southwest deal was found by Cheapflights users on 9/15. 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 10/255:50 amPSP - MDW
2 stops7h 50mSouthwest
Wed 10/293:25 pmMDW - PSP
2 stops8h 05mSouthwest
Deal found 9/15$279
This Delta deal was found by Cheapflights users on 9/16. 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.
Mon 11/2412:33 pmPSP - MDW
1 stop8h 59mDelta
Thu 11/276:00 amMDW - PSP
1 stop7h 28mDelta
Deal found 9/16$289
This Southwest deal was found by Cheapflights users on 9/15. 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.
Fri 10/244:10 pmPSP - MDW
1 stop5h 20mSouthwest
Mon 10/274:30 pmMDW - PSP
2 stops8h 30mSouthwest
Deal found 9/15$294
This Southwest deal was found by Cheapflights users on 9/15. 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 10/410:35 amPSP - MDW
1 stop8h 10mSouthwest
Tue 10/145:20 pmMDW - PSP
1 stop6h 10mSouthwest
Deal found 9/15$304
This Southwest deal was found by Cheapflights users on 9/15. 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 11/42:40 pmPSP - MDW
1 stop12h 25mSouthwest
Fri 11/73:40 pmMDW - PSP
1 stop9h 15mSouthwest
Deal found 9/15$310
This Southwest deal was found by Cheapflights users on 9/16. 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 10/304:10 pmPSP - MDW
1 stop5h 20mSouthwest
Fri 11/73:40 pmMDW - PSP
1 stop9h 15mSouthwest
Deal found 9/16$314
This Southwest deal was found by Cheapflights users on 9/14. 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.
Fri 10/174:10 pmPSP - MDW
1 stop5h 20mSouthwest
Fri 10/2412:00 pmMDW - PSP
1 stop5h 25mSouthwest
Deal found 9/14$331

Cheapflights Fare Finder

 
Customize your flight search to find flights from Palm Springs to Midway 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 September 17, 2025.
Use the filters below to find and compare flights from Palm Springs to Chicago Midway Airport that are best for you.

Fly from

Palm Springs

Fly to

Midway

Route

Depart

Return

Price

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 10/21

3:10 pm-10:40 pm

1 stop5h 30m

Chicago Midway

Tue 10/28

8:00 am-12:25 pm

1 stop6h 25m

$269

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 10/25

5:50 am-3:40 pm

2 stops7h 50m

Chicago Midway

Wed 10/29

8:00 am-12:25 pm

1 stop6h 25m

$274

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 1/6

11:15 am-10:40 pm

1 stop9h 25m

Chicago Midway

Wed 1/21

2:10 pm-9:40 pm

1 stop9h 30m

$281

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Mon 11/24

12:33 pm-11:32 pm

1 stop8h 59m

Chicago Midway

Thu 11/27

6:00 am-11:28 am

1 stop7h 28m

$289

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 11/14

3:55 pm-12:20 am

1 stop6h 25m

Chicago Midway

Mon 11/17

12:20 pm-4:45 pm

1 stop6h 25m

$289

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 10/24

4:10 pm-11:30 pm

1 stop5h 20m

Chicago Midway

Mon 10/27

4:30 pm-11:00 pm

2 stops8h 30m

$294

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 12/20

11:45 am-5:25 pm

Nonstop3h 40m

Chicago Midway

Sat 1/3

5:30 pm-12:05 am

1 stop8h 35m

$299

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 10/4

10:35 am-8:45 pm

1 stop8h 10m

Chicago Midway

Tue 10/14

5:20 pm-9:30 pm

1 stop6h 10m

$304

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 1/13

12:45 pm-9:50 pm

1 stop7h 05m

$126

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 1/31

11:55 am-8:30 pm

1 stop6h 35m

$126

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 19 results
1
2

Best time to book a flight from Palm Springs to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Palm Springs 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 Palm Springs to Chicago Midway Airport

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

Currently, April is the cheapest month in which you can book a flight from Palm Springs to Chicago Midway Airport (average of $160). Flying from Palm Springs to Chicago Midway Airport in November is currently the most expensive (average of $249). 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.

What is the cheapest time of day to fly from PSP to MDW?

Find hourly flight availability from Palm Springs to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 17, 2025.

A simple way to save on the total cost of your ticket is to fly from Palm Springs to Chicago Midway Airport in the afternoon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight at noon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated September 17, 2025.
Read reviews from past customers who have flown Southwest from Palm Springs to Chicago Midway Airport. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Comfort

8.0

Entertainment

7.5

Food

7.0

Boarding

8.1

Crew

8.6

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 Palm Springs to Midway. 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 from for flights from Palm Springs to Chicago Midway?

    Palm Springs (PSP) is the airport you will fly out of if you book a flight from Palm Springs to Chicago Midway. You should not have trouble finding flights to Chicago Midway from Palm Springs; the airport handles an average of 0 outbound flights to Chicago Midway per day. You should also have plenty of airline options to choose from since 1 airline has flights from the Palm Springs airport to Chicago Midway. It is only a 2.2 mi journey to Palm Springs (PSP) from Palm Springs’s city center.

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

    Airlines like Southwest fly from Palm Springs to Chicago Midway Airport in about 5h 30m. The time it takes to get you to your destination can typically vary by up to . The distance from Palm Springs to Chicago Midway Airport is about 1653 mi.

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

    Southwest, at $288, was found to be the cheapest airline from Palm Springs to Chicago Midway Airport.. Southwest is currently priced 28% below the average price you’ll pay for this route.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Palm Springs to Midway 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 Palm Springs to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Palm Springs to Chicago Midway Airport (average of $160). Flying from Palm Springs to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top airline flying from Palm Springs to Midway

Discover the top airline that operate flights from Palm Springs to Midway. 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$399FlexibilityNo cancel feeOn-time63%

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