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Midway

$153+ 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 1/15. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
Dec 21 — Dec 281
Sun 12/21
Sun 12/28
1 adult, Economy
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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 November 21, 2025.

This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:00 amPSP - MDW
2 stops9h 19mDelta
Thu 1/16:00 amMDW - PSP
1 stop8h 55mDelta
Deal found 11/19$350
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/612:37 pmPSP - MDW
1 stop9h 10mDelta
Sat 12/136:00 amMDW - PSP
1 stop7h 27mDelta
Deal found 11/19$359
This Southwest deal was found by Cheapflights users on 11/20. 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.
Thu 12/2511:05 amPSP - MDW
1 stop7h 00mSouthwest
Thu 1/18:25 amMDW - PSP
1 stop7h 40mSouthwest
Deal found 11/20$362
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1512:37 pmPSP - MDW
1 stop9h 10mDelta
Tue 1/69:50 amMDW - PSP
1 stop6h 39mDelta
Deal found 11/19$366
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/1412:37 pmPSP - MDW
1 stop9h 10mDelta
Tue 1/69:50 amMDW - PSP
1 stop6h 39mDelta
Deal found 11/19$401
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/912:37 pmPSP - MDW
1 stop9h 10mDelta
Fri 12/126:00 amMDW - PSP
1 stop7h 27mDelta
Deal found 11/19$404
This Southwest deal was found by Cheapflights users on 11/19. 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.
Thu 12/185:35 amPSP - MDW
1 stop5h 30mSouthwest
Sun 12/219:50 amMDW - PSP
Nonstop4h 20mSouthwest
Deal found 11/19$410
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/412:37 pmPSP - MDW
1 stop9h 10mDelta
Sat 12/66:00 amMDW - PSP
1 stop7h 27mDelta
Deal found 11/19$424

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 November 21, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$349
(Southwest)

One-way from

$153
(Kiwi.com)

Popular in

December

Cheapest in

July

Average price

$404

Good one-way deal

$393 or less
Provider with most accurate pricing for Palm Springs-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Palm Springs-Chicago Midway flights.
Search Deals
From Palm Springs to Chicago Midway
Search Deals
One-way flight from Palm Springs to Chicago Midway
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($64 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a one-way flight from Palm Springs to Chicago Midway.
Search Deals

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 November 21, 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

Wed 1/14

12:45 pm-9:50 pm

1 stop7h 05m

Chicago Midway

Sun 1/18

5:35 pm-9:40 pm

1 stop6h 05m

$349

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 12/25

6:00 am-5:19 pm

2 stops9h 19m

Chicago Midway

Thu 1/1

6:00 am-12:55 pm

1 stop8h 55m

$350

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 1/21

1:29 pm-10:22 pm

1 stop6h 53m

Chicago Midway

Wed 1/28

9:50 am-2:29 pm

1 stop6h 39m

$353

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 1/21

1:29 pm-10:22 pm

1 stop6h 53m

Chicago Midway

Sat 1/24

6:00 am-11:56 am

1 stop7h 56m

$356

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 1/24

1:06 pm-10:22 pm

1 stop7h 16m

Chicago Midway

Tue 1/27

9:50 am-2:29 pm

1 stop6h 39m

$356

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 1/24

1:06 pm-10:22 pm

1 stop7h 16m

Chicago Midway

Wed 1/28

9:50 am-2:29 pm

1 stop6h 39m

$356

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 12/6

12:37 pm-11:47 pm

1 stop9h 10m

Chicago Midway

Wed 12/10

6:00 am-11:27 am

1 stop7h 27m

$359

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 12/6

12:37 pm-11:47 pm

1 stop9h 10m

Chicago Midway

Sat 12/13

6:00 am-11:27 am

1 stop7h 27m

$359

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 12/3

12:37 pm-11:47 pm

1 stop9h 10m

Chicago Midway

Sat 12/6

6:00 am-11:27 am

1 stop7h 27m

$359

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 12/25

11:05 am-8:05 pm

1 stop7h 00m

Chicago Midway

Thu 1/1

8:25 am-2:05 pm

1 stop7h 40m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 19 results
1
2

Compare providers for flights from Palm Springs to Midway

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 Palm Springs to Midway in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust 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 Palm Springs-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Palm Springs-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Palm Springs-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Palm Springs-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams 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 Palm Springs-Chicago Midway Airport 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 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 $110). Flying from Palm Springs to Chicago Midway Airport in August is currently the most expensive (average of $228). 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 November 21, 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 22% on your trip compared to booking a flight in the evening.

How much does it cost to fly round-trip from Palm Springs to Chicago Midway Airport?

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 November 21, 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
4,251 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

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
4,251 reviews
Southwest
8.0
Very good
4,251 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Crew

8.6

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 and Delta fly from Palm Springs to Chicago Midway Airport in about 7h 05m. The time it takes to get you to your destination can typically vary by up to 2h 14m. 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 flights from Palm Springs to Chicago Midway Airport?

    The cheapest flight price from Palm Springs to Chicago Midway Airport is $377. On average you can expect to pay $437. The most popular route, (Palm Springs - Chicago Midway), can usually be booked for $349.

  • 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 $110). Flying from Palm Springs to Chicago Midway Airport in August is currently the most expensive (average of $228). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 November 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$396FlexibilityNo cancel feeOn-time63%

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