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Midway

$82+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
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 agosto 20, 2025.

Round-trip from

$192
(Frontier)

One-way from

$82
(Priceline)

Popular in

September

Cheapest in

July

Average price

$448

Good one-way deal

$303 or less
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. 13% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a one-way flight from Palm Springs to Chicago Midway.
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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 agosto 20, 2025.

This Frontier deal was found by Cheapflights users on 8/18. 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.
lun. 10/2712:00 pmPSP - MDW
1 stop10h 24mFrontier
jue. 10/309:43 pmMDW - PSP
2 stops15h 24mFrontier
Deal found 8/18$192
This Southwest deal was found by Cheapflights users on 8/18. 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.
vie. 11/710:30 amPSP - MDW
1 stop7h 55mSouthwest
sáb. 11/152:40 pmMDW - PSP
1 stop5h 55mSouthwest
Deal found 8/18$270
This Delta deal was found by Cheapflights users on 8/18. 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.
vie. 11/74:59 pmPSP - MDW
2 stops14h 41mDelta
sáb. 11/152:00 pmMDW - PSP
2 stops9h 34mDelta
Deal found 8/18$283
This Southwest deal was found by Cheapflights users on 8/18. 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.
mié. 9/1011:00 amPSP - MDW
1 stop5h 10mSouthwest
mié. 9/174:35 pmMDW - PSP
1 stop6h 20mSouthwest
Deal found 8/18$287
This Southwest deal was found by Cheapflights users on 8/19. 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.
vie. 9/263:20 pmPSP - MDW
1 stop6h 45mSouthwest
lun. 9/296:15 pmMDW - PSP
1 stop5h 55mSouthwest
Deal found 8/19$306
This Southwest deal was found by Cheapflights users on 8/19. 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.
mié. 11/55:30 amPSP - MDW
1 stop6h 10mSouthwest
dom. 11/97:50 amMDW - PSP
1 stop10h 45mSouthwest
Deal found 8/19$307
This Southwest deal was found by Cheapflights users on 8/19. 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.
mié. 9/175:30 amPSP - MDW
1 stop5h 45mSouthwest
mar. 9/2312:10 pmMDW - PSP
1 stop6h 45mSouthwest
Deal found 8/19$321
This Delta deal was found by Cheapflights users on 8/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/1712:20 pmPSP - MDW
2 stops18h 20mDelta
mar. 9/231:08 pmMDW - PSP
2 stops10h 12mDelta
Deal found 8/20$327

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 agosto 20, 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

lun. 10/27

12:00 pm-12:24 am

1 stop10h 24m

Chicago Midway

jue. 10/30

9:43 pm-11:07 am

2 stops15h 24m

$192

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 11/7

10:30 am-8:25 pm

1 stop7h 55m

Chicago Midway

sáb. 11/15

2:40 pm-6:35 pm

1 stop5h 55m

$270

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 11/7

4:59 pm-9:40 am

2 stops14h 41m

Chicago Midway

sáb. 11/15

2:00 pm-9:34 pm

2 stops9h 34m

$283

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

mié. 9/10

11:00 am-6:10 pm

1 stop5h 10m

Chicago Midway

mié. 9/17

4:35 pm-8:55 pm

1 stop6h 20m

$287

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

jue. 11/6

10:30 am-8:25 pm

1 stop7h 55m

Chicago Midway

lun. 11/10

9:25 am-3:50 pm

1 stop8h 25m

$306

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 9/26

3:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

lun. 9/29

6:15 pm-10:10 pm

1 stop5h 55m

$306

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

mié. 11/5

5:30 am-1:40 pm

1 stop6h 10m

Chicago Midway

dom. 11/9

7:50 am-4:35 pm

1 stop10h 45m

$307

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

mié. 9/17

5:30 am-1:15 pm

1 stop5h 45m

Chicago Midway

mar. 9/23

12:10 pm-4:55 pm

1 stop6h 45m

$321

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 9/26

3:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

mar. 9/30

12:10 pm-4:55 pm

1 stop6h 45m

$321

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 10/10

12:00 pm-12:24 am

1 stop10h 24m

$82

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 16 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 agosto 20, 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 agosto 20, 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
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

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
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

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 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 Frontier, Southwest, and Delta fly from Palm Springs to Chicago Midway Airport in about 7h 55m. The time it takes to get you to your destination can typically vary by up to 6h 46m. 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 27% below the average price you’ll pay for this route.

  • What are the cheapest flights from Palm Springs to Chicago Midway Airport?

    The cheapest flight price from Palm Springs to Chicago Midway Airport is $290. On average you can expect to pay $325. The most popular route, (Palm Springs - Chicago Midway), can usually be booked for $192.

  • 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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Alternative routes for Palm Springs to Midway

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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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$400FlexibilityNo cancel feeOn-time63%

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