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Midway

$80+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
10月 15 — 10月 221
週三 10/15
週三 10/22
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 9月 15, 2025.

Round-trip from

$259
(Southwest)

One-way from

$80
(Southwest)

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 9月 15, 2025.

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.
週六 11/2211:45 amPSP - MDW
Nonstop3h 40mSouthwest
週六 11/296:05 amMDW - PSP
1 stop5h 55mSouthwest
Deal found 9/14$259
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週五 10/1712:00 pmPSP - MDW
1 stop10h 24mFrontier
週日 10/199:26 pmMDW - PSP
2 stops15h 49mFrontier
Deal found 9/14$264
This Delta deal was found by Cheapflights users on 9/13. 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.
週一 11/2412:33 pmPSP - MDW
1 stop8h 59mDelta
週四 11/276:00 amMDW - PSP
1 stop7h 28mDelta
Deal found 9/13$269
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.
週四 10/3011:05 amPSP - MDW
1 stop7h 30mSouthwest
週六 11/82:40 pmMDW - PSP
1 stop5h 55mSouthwest
Deal found 9/14$279
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.
週五 11/215:35 amPSP - MDW
2 stops8h 45mSouthwest
週六 11/296:05 amMDW - PSP
1 stop5h 55mSouthwest
Deal found 9/14$284
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.
週五 11/143:55 pmPSP - MDW
1 stop6h 25mSouthwest
週一 11/1712:20 pmMDW - PSP
1 stop6h 25mSouthwest
Deal found 9/14$289
This Southwest deal was found by Cheapflights users on 9/13. 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.
週五 10/34:10 pmPSP - MDW
1 stop5h 20mSouthwest
週二 10/78:00 amMDW - PSP
1 stop6h 25mSouthwest
Deal found 9/13$304
This Southwest deal was found by Cheapflights users on 9/13. 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.
週二 11/251:00 pmPSP - MDW
Nonstop3h 45mSouthwest
週二 12/28:25 amMDW - PSP
1 stop7h 40mSouthwest
Deal found 9/13$311
This Kiwi.com deal was found by Cheapflights users on 9/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
週日 9/281:19 pmPSP - MDW
1 stop24h 34mFrontier
週四 10/21:53 pmMDW - PSP
2 stops23h 53mFrontier
Deal found 9/13$312
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.
週四 10/309:50 amPSP - MDW
1 stop7h 50mSouthwest
週五 11/73:40 pmMDW - PSP
1 stop9h 15mSouthwest
Deal found 9/14$314

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 9月 15, 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

週六 11/22

11:45 am-5:25 pm

Nonstop3h 40m

Chicago Midway

週六 11/29

6:05 am-10:00 am

1 stop5h 55m

$259

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週五 10/17

12:00 pm-12:24 am

1 stop10h 24m

Chicago Midway

週日 10/19

9:26 pm-11:15 am

2 stops15h 49m

$264

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週一 11/24

12:33 pm-11:32 pm

1 stop8h 59m

Chicago Midway

週四 11/27

6:00 am-11:28 am

1 stop7h 28m

$269

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週四 10/30

11:05 am-8:35 pm

1 stop7h 30m

Chicago Midway

週六 11/8

2:40 pm-6:35 pm

1 stop5h 55m

$279

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週五 11/21

4:25 pm-12:05 am

1 stop5h 40m

Chicago Midway

週六 11/29

6:05 am-10:00 am

1 stop5h 55m

$279

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週一 12/22

1:00 pm-6:45 pm

Nonstop3h 45m

Chicago Midway

週一 12/29

6:20 pm-11:40 pm

2 stops7h 20m

$284

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週五 11/14

3:55 pm-12:20 am

1 stop6h 25m

Chicago Midway

週一 11/17

12:20 pm-4:45 pm

1 stop6h 25m

$289

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週五 10/3

4:10 pm-11:30 pm

1 stop5h 20m

Chicago Midway

週二 10/7

8:00 am-12:25 pm

1 stop6h 25m

$304

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週二 11/25

1:00 pm-6:45 pm

Nonstop3h 45m

Chicago Midway

週二 12/2

8:25 am-2:05 pm

1 stop7h 40m

$311

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

週四 10/30

9:50 am-7:40 pm

1 stop7h 50m

Chicago Midway

週五 11/7

3:40 pm-10:55 pm

1 stop9h 15m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 20 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 9月 15, 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 9月 15, 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
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

Comfort

8.0

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, Frontier, and Delta fly from Palm Springs to Chicago Midway Airport in about 3h 40m. The time it takes to get you to your destination can typically vary by up to 6h 44m. The distance from Palm Springs to Chicago Midway Airport is about 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 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.

  • What are the cheapest airlines to fly from Palm Springs to Chicago Midway Airport one-way?

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $80. Frontier flights start at $90 while deals on Delta start at $129 one-way.

  • 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 9月 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$402FlexibilityNo cancel feeOn-time63%

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