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$72+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — MDW
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$289
(Southwest)

One-way from

$72
(Priceline)

Popular in

September

Cheapest in

July

Average price

$288

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. 15% potential increase in price ($72 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 July 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 July 3, 2025.

This Southwest deal was found by Cheapflights users on 7/1. 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 7/2510:45 amPSP - MDW
1 stop8h 30mSouthwest
Mon 7/287:05 pmMDW - PSP
1 stop5h 50mSouthwest
Deal found 7/1$289
This Delta deal was found by Cheapflights users on 7/3. 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 9/166:02 amPSP - MDW
2 stops9h 33mDelta
Tue 9/239:20 amMDW - PSP
2 stops9h 04mDelta
Deal found 7/3$297
This Frontier deal was found by Cheapflights users on 7/3. 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.
Fri 10/1712:45 pmPSP - MDW
1 stop7h 53mFrontier
Sun 10/1910:56 pmMDW - PSP
2 stops14h 59mFrontier
Deal found 7/3$310

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 July 3, 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

Fri 7/25

10:45 am-9:15 pm

1 stop8h 30m

Chicago Midway

Mon 7/28

7:05 pm-10:55 pm

1 stop5h 50m

$289

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 9/16

6:02 am-5:35 pm

2 stops9h 33m

Chicago Midway

Tue 9/23

9:20 am-4:24 pm

2 stops9h 04m

$297

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 10/17

12:45 pm-10:38 pm

1 stop7h 53m

Chicago Midway

Sun 10/19

10:56 pm-11:55 am

2 stops14h 59m

$310

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Mon 10/13

12:45 pm-10:38 pm

1 stop7h 53m

$72

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 12/6

10:45 am-8:25 pm

1 stop7h 40m

$113

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 9/18

5:49 pm-4:43 pm

2 stops20h 54m

$207

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 10/11

6:00 am-6:36 pm

2 stops10h 36m

$245

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 July 3, 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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and Frontier 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
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,266 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,982 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Frontier
5.9
Fair
3,286 reviews
Southwest
8.0
Very good
4,266 reviews

Boarding

8.2

Crew

8.6

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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.

  • What are the cheapest airlines flying from Palm Springs to Chicago Midway Airport round-trip?

    Southwest, at $289, was found to be the cheapest airline from Palm Springs to Chicago Midway Airport.Alternate airlines to your destination round-trip include Delta and Frontier. 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 Frontier, which is currently one of the cheapest options available, starting at $72. Southwest flights start at $113 while deals on Delta start at $245 one-way.

  • 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 $270.

  • 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 Palm Springs?

Book flights to Palm Springs if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$288Average$406FlexibilityNo cancel feeOn-time63%

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