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$165+ 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
Apr 27 — May 41
Mon 4/27
Mon 5/4
1 adult, Economy
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Cheap 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 March 28, 2026.

This Southwest deal was found by Cheapflights users on 3/25. 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 4/296:25 pm
PSP
-
MDW
1 stop9h 20m
Southwest
Sat 5/22:30 pm
MDW
-
PSP
1 stop6h 30m
Southwest
Deal found 3/25$195
This Southwest deal was found by Cheapflights users on 3/26. 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 4/256:50 am
PSP
-
MDW
1 stop5h 45m
Southwest
Wed 4/2910:20 am
MDW
-
PSP
1 stop9h 30m
Southwest
Deal found 3/26$199
This Southwest deal was found by Cheapflights users on 3/26. 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 5/96:05 am
PSP
-
MDW
2 stops9h 10m
Southwest
Wed 5/136:30 am
MDW
-
PSP
1 stop5h 45m
Southwest
Deal found 3/26$205
This Southwest deal was found by Cheapflights users on 3/26. 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 4/256:50 am
PSP
-
MDW
1 stop5h 45m
Southwest
Sat 5/22:30 pm
MDW
-
PSP
1 stop6h 30m
Southwest
Deal found 3/26$211
This Southwest deal was found by Cheapflights users on 3/24. 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 6/44:10 pm
PSP
-
MDW
1 stop7h 15m
Southwest
Tue 6/92:35 pm
MDW
-
PSP
2 stops9h 30m
Southwest
Deal found 3/24$234
This Southwest deal was found by Cheapflights users on 3/24. 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 5/46:50 pm
PSP
-
MDW
1 stop9h 10m
Southwest
Sat 5/92:40 pm
MDW
-
PSP
1 stop6h 20m
Southwest
Deal found 3/24$241
This Delta deal was found by Cheapflights users on 3/25. 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 4/251:27 pm
PSP
-
MDW
1 stop7h 01m
Delta
Sat 5/25:40 am
MDW
-
PSP
1 stop8h 36m
Delta
Deal found 3/25$250

Find 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 March 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$195
(Southwest)

One-way from

$165
(Southwest)

Popular in

December

Cheapest in

July

Average price

$567
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. 20% potential increase in price ($119 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 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 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 March 28, 2026.
Use the filters below to find and compare flights from Palm Springs to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 4/29

6:40 am-5:00 pm

2 stops8h 20m

Chicago Midway

Sat 5/2

6:00 am-1:00 pm

2 stops9h 00m

$210

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Mon 5/4

6:50 pm-5:50 am

2 stops9h 00m

Chicago Midway

Sat 5/9

2:40 pm-7:00 pm

1 stop6h 20m

$246
Quickest round-trip

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 4/18

6:05 am-5:15 pm

2 stops9h 10m

Chicago Midway

Tue 4/21

6:30 am-10:15 am

1 stop5h 45m

$256

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 4/22

1:27 pm-10:28 pm

1 stop7h 01m

Chicago Midway

Sun 4/26

6:00 am-12:16 pm

1 stop8h 16m

$293

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 4/23

6:50 pm-5:00 am

2 stops8h 10m

Chicago Midway

Thu 4/30

10:05 am-5:35 pm

2 stops9h 30m

$356

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 6/4

4:10 pm-1:25 am

1 stop7h 15m

Chicago Midway

Fri 6/12

4:15 pm-10:10 pm

1 stop7h 55m

$391

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 7/30

9:55 am-8:40 pm

2 stops8h 45m

Chicago Midway

Tue 8/4

10:30 am-4:50 pm

2 stops8h 20m

$408
Cheapest one-way

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Mon 6/29

7:30 pm-5:45 am

1 stop8h 15m

$175
Quickest one-way

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 4/28

1:27 pm-10:28 pm

1 stop7h 01m

$190

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 5/26

6:25 pm-5:45 am

1 stop9h 20m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 19 resultsSorted by cheapest first
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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Palm Springs-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 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 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, November is the cheapest month in which you can book a flight from Palm Springs to Chicago Midway Airport (average of $130). 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 March 28, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Palm Springs to Chicago Midway Airport as you normally would.

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 March 28, 2026.
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
4,333 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,333 reviews
Southwest
8.0
Very good
4,333 reviews

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 9h 20m. 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 $273, was found to be the cheapest airline from Palm Springs to Chicago Midway Airport.. Southwest is currently priced 39% 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, November is the cheapest month in which you can book a flight from Palm Springs to Chicago Midway Airport (average of $130). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

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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 March 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$273Average$358FlexibilityNo cancel feeOn-time63%

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