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$71+ Cheap flights from Palm Springs (PSP) to Chicago (CHI)

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 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find cheap flights from Palm Springs to Chicago with Cheapflights

1. Tell us where you want to go

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3. Compare prices and book

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Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in August or May, booked 23 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Find flight deals from Palm Springs to Chicago

Cheapest flights from Palm Springs to Chicago
Explore the most affordable flight options available from Palm Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2025.

This Priceline deal was found by Cheapflights users on 10/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1411:52 amPSP - ORD
1 stop10h 23mFrontier
Mon 11/176:00 amORD - PSP
1 stop7h 07mFrontier
Deal found 10/27$182
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:25 pmPSP - ORD
Nonstop3h 59mAmerican Airlines
Thu 11/273:00 pmORD - PSP
Nonstop4h 25mAmerican Airlines
Deal found 10/27$242
This Sun Country Air deal was found by Cheapflights users on 10/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/236:18 pmPSP - ORD
1 stop14h 21mSun Country Air
Fri 11/288:40 pmORD - PSP
1 stop13h 26mSun Country Air
Deal found 10/26$252
This Delta deal was found by Cheapflights users on 10/29. 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 11/2412:33 pmPSP - ORD
1 stop9h 29mDelta
Thu 11/275:23 amORD - PSP
1 stop8h 00mDelta
Deal found 10/29$281
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:00 amPSP - ORD
Nonstop3h 58mAmerican Airlines
Wed 12/38:30 amORD - PSP
Nonstop4h 24mAmerican Airlines
Deal found 10/28$293
This American Airlines deal was found by Cheapflights users on 10/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:25 pmPSP - ORD
Nonstop3h 59mAmerican Airlines
Wed 12/310:19 amORD - PSP
Nonstop4h 26mAmerican Airlines
Deal found 10/28$294
This American Airlines deal was found by Cheapflights users on 10/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/243:25 pmPSP - ORD
Nonstop3h 59mAmerican Airlines
Sat 11/2912:07 pmORD - PSP
Nonstop4h 24mAmerican Airlines
Deal found 10/29$300
This Frontier deal was found by Cheapflights users on 10/27. 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.
Sat 11/2211:47 amPSP - ORD
1 stop10h 23mFrontier
Tue 11/257:00 amORD - PSP
1 stop6h 02mFrontier
Deal found 10/27$303
This Southwest deal was found by Cheapflights users on 10/28. 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 11/277:20 amPSP - MDW
1 stop5h 20mSouthwest
Wed 12/312:20 pmMDW - PSP
1 stop6h 25mSouthwest
Deal found 10/28$313
This Delta deal was found by Cheapflights users on 10/28. 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 11/2712:33 pmPSP - MDW
1 stop9h 07mDelta
Wed 12/39:59 amMDW - PSP
2 stops8h 17mDelta
Deal found 10/28$318
This Delta deal was found by Cheapflights users on 10/29. 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 11/2412:33 pmPSP - MDW
1 stop9h 07mDelta
Thu 11/276:00 amMDW - PSP
1 stop7h 23mDelta
Deal found 10/29$330
This Southwest deal was found by Cheapflights users on 10/28. 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 11/261:00 pmPSP - MDW
Nonstop3h 45mSouthwest
Wed 12/39:45 amMDW - PSP
1 stop6h 20mSouthwest
Deal found 10/28$342

Cheap flight deals from Palm Springs to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Palm Springs (PSP) to Chicago (CHI). 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 October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$182
(Priceline)

One-way from

$71
(Frontier)

Popular in

September

Cheapest in

August

Average price

$369

Good round-trip deal

$333 or less

Good one-way deal

$207 or less
Provider with most accurate pricing for Palm Springs-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Palm Springs-Chicago (CHI) flights.
Search Deals
From Palm Springs to Chicago (CHI)
Search Deals
One-way flight from Palm Springs to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a round-trip flight from Palm Springs to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Palm Springs to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Palm Springs to Chicago 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 October 29, 2025.
Use the filters below to find and compare flights from Palm Springs to Chicago that are best for you.

Fly from

Palm Springs

Fly to

Chicago

Route

Depart

Return

Price

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Sun 11/23

6:18 pm-10:39 am

1 stop14h 21m

Chicago O'Hare Intl

Fri 11/28

11:00 am-4:36 pm

1 stop7h 36m

$265

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 11/26

5:36 pm-8:20 am

1 stop12h 44m

Chicago O'Hare Intl

Mon 12/1

8:22 pm-4:30 pm

1 stop22h 08m

$305

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 11/27

12:33 pm-11:40 pm

1 stop9h 07m

Chicago Midway

Wed 12/3

6:00 am-11:27 am

1 stop7h 27m

$313

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 11/27

7:20 am-2:40 pm

1 stop5h 20m

Chicago Midway

Wed 12/3

12:20 pm-4:45 pm

1 stop6h 25m

$313

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 1/14

5:26 pm-2:38 pm

1 stop19h 12m

Chicago O'Hare Intl

Wed 1/21

8:00 am-4:32 pm

1 stop10h 32m

$318

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 12/2

11:02 am-4:57 pm

Nonstop3h 55m

Chicago O'Hare Intl

Sun 12/7

9:11 am-11:42 am

Nonstop4h 31m

$320

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Mon 11/24

3:25 pm-9:24 pm

Nonstop3h 59m

Chicago O'Hare Intl

Mon 12/1

8:25 am-10:49 am

Nonstop4h 24m

$325

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Sat 2/14

7:00 am-12:54 pm

Nonstop3h 54m

Chicago O'Hare Intl

Mon 2/16

9:20 am-12:00 pm

Nonstop4h 40m

$325

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Mon 11/24

12:33 pm-12:02 am

1 stop9h 29m

Chicago O'Hare Intl

Thu 11/27

5:23 am-11:23 am

1 stop8h 00m

$330

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 12/9

4:22 pm-11:59 pm

1 stop5h 37m

Chicago O'Hare Intl

Thu 12/11

9:11 am-11:42 am

Nonstop4h 31m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 43 results
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Compare providers for flights from Palm Springs to Chicago

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 Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 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 flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Palm Springs-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Palm Springs-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from Palm Springs to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Palm Springs to Chicago. Price data was last updated on October 24, 2025.

Booking 23 days in advance of your planned departure date is, on average, the best time to get cheap flights from Palm Springs to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

What is the cheapest month to book a flight from Palm Springs to Chicago?

Currently, February is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $93). Flying from Palm Springs to Chicago in May is currently the most expensive (average of $173). 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 CHI?

Find hourly flight availability from Palm Springs to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 29, 2025.

When flying from Palm Springs to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the afternoon, which can drop the price by up to 30% versus a flight in the evening.

What is the cheapest day to fly from Palm Springs to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Palm Springs to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Palm Springs to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Monday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

What’s the top layover airport for flights from Palm Springs to Chicago?

Share of 1-stop round-trip flights from Palm Springs to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Las Vegas (LAS) – chosen by Cheapflights users on 63% of 1-stop itineraries from Palm Springs to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Palm Springs to Chicago?

Average round-trip fare for 1-stop flights from Palm Springs to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Denver (DEN) is the most affordable 1-stop option, with an average round-trip price of $144.

What’s the fastest layover option from Palm Springs to Chicago?

Shortest average travel time for 1-stop one-way flights from Palm Springs to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Las Vegas (LAS) have the shortest average one-way travel time for 1-stop routes: 6h 00m.

Which airport typically offers the quickest layover for flights from Palm Springs to Chicago?

Average layover duration for 1-stop one-way flights from Palm Springs to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Las Vegas (LAS) offer the fastest connection on this route, with an average layover time of 1h 13m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated October 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Palm Springs to Chicago. 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
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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.
Delta
7.9
Good
7,992 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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.
United Airlines
7.4
Good
8,999 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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.
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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.
Frontier
5.8
Fair
3,124 reviews
Southwest
8.0
Very good
4,241 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Comfort

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 Chicago. 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?

    Most people fly from Palm Springs (PSP) if they book a flight from Palm Springs to Chicago. On average, Palm Springs has 2 outbound flights to Chicago per day from 4 airlines. Palm Springs is conveniently located just 2.2 mi from Palm Springs’s city center.

  • How long is the flight from Palm Springs to Chicago?

    Sun Country Air, Delta, and Southwest can get you from Palm Springs to Chicago in just under 5h 20m. Your travel time can differ by up to 9h 01m. Palm Springs and Chicago are separated by a distance of 1653 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on Delta is currently your cheapest option to Chicago, with prices starting at $179. Additional round-trip tickets that might be worth considering are offered by Southwest and American Airlines, with the lowest prices starting at $250 and $252, respectively. These flights start at 56% lower than the current average price 3 months from now.

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

    To fly one-way, consider booking your trip with United Airlines, which is currently one of the cheapest options available, starting at $116. Delta flights start at $126 while deals on Sun Country Air start at $128 one-way.

  • What are the most reliable airlines from Palm Springs to Chicago?

    Before booking your flight to Chicago from Palm Springs, check out the most reliable airlines to get you to your destination on time: Emirates (100%), United Airlines (100%), Lufthansa( 100%).

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

    Looking for the cheapest flight from Palm Springs to Chicago? While on average our users pay $456, our data indicates the cheapest price to be $143. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $265.

  • Can I find deals for flights from Palm Springs to Chicago that include hotel bookings?

    Yes. In addition to deals on Palm Springs to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Palm Springs to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Palm Springs to Chicago.

  • Can I find deals for business class flights from Palm Springs to Chicago?

    Yes. Cheapflights offers flight deals from Palm Springs to Chicago 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?

    Currently, February is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $93). Flying from Palm Springs to Chicago in May is currently the most expensive (average of $173). 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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Alternative routes for Palm Springs to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Palm Springs to Chicago

Discover the top 4 airlines that operate flights from Palm Springs to Chicago. 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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$179Average$297FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$250Average$394FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$252Average$391FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$268Average$437FlexibilityNo cancel feeOn-time69%

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