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$153+ 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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
Apr 16 — Apr 231
Wed 4/16
Wed 4/23
1 adult, Economy
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Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in May or August, booked 42 days in advance, depart on a Wednesday or Thursday and return on a Monday

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 April 11, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(United Airlines)

One-way from

$153
(Booking.com)

Popular in

July

Cheapest in

May

Average price

$500

Good round-trip deal

$334 or less

Good one-way deal

$230 or less
Provider with most accurate pricing for Palm Springs-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Palm Springs-Chicago (CHI) flights.
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From Palm Springs to Chicago (CHI)
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One-way flight from Palm Springs to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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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).
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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 April 11, 2025.

This Frontier deal was found by Cheapflights users on 4/10. 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.
Thu 4/1712:25 pmPSP - MDW
1 stop9h 56mFrontier
Mon 4/216:45 amMDW - PSP
1 stop6h 56mFrontier
Deal found 4/10$198
This Frontier deal was found by Cheapflights users on 4/9. 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 4/1112:15 pmPSP - ORD
1 stop10h 22mFrontier
Mon 4/146:40 amORD - PSP
1 stop7h 01mFrontier
Deal found 4/9$198
This United Airlines deal was found by Cheapflights users on 4/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/35:20 amPSP - ORD
1 stop5h 55mUnited Airlines
Sat 5/179:30 amORD - PSP
Nonstop4h 39mUnited Airlines
Deal found 4/10$241
This Alaska Airlines deal was found by Cheapflights users on 4/9. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/308:20 amPSP - ORD
1 stop8h 00mAlaska Airlines
Sat 5/312:00 pmORD - PSP
1 stop8h 17mAlaska Airlines
Deal found 4/9$246
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Sat 5/31:57 pmPSP - ORD
Nonstop3h 59mAmerican Airlines
Sat 5/1710:05 amORD - PSP
Nonstop4h 24mAmerican Airlines
Deal found 4/10$250
This Delta deal was found by Cheapflights users on 4/9. 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 6/312:24 pmPSP - ORD
1 stop7h 16mDelta
Wed 6/47:30 amORD - PSP
1 stop6h 14mDelta
Deal found 4/9$257
This Delta deal was found by Cheapflights users on 4/10. 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 5/312:30 pmPSP - MDW
1 stop7h 52mDelta
Sat 5/176:00 amMDW - PSP
2 stops12h 28mDelta
Deal found 4/10$262
This Hawaiian Airlines deal was found by Cheapflights users on 4/11. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/38:20 amPSP - ORD
1 stop8h 50mHawaiian Airlines
Mon 5/56:00 amORD - PSP
1 stop9h 12mHawaiian Airlines
Deal found 4/11$269
This Sun Country Air deal was found by Cheapflights users on 4/10. 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.
Thu 4/246:10 pmPSP - ORD
1 stop17h 13mSun Country Air
Sun 4/278:15 amORD - PSP
1 stop10h 49mSun Country Air
Deal found 4/10$275
This Southwest deal was found by Cheapflights users on 4/10. 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 8/73:20 pmPSP - MDW
1 stop6h 45mSouthwest
Wed 8/202:15 pmMDW - PSP
1 stop8h 40mSouthwest
Deal found 4/10$289
This Expedia deal was found by Cheapflights users on 4/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1712:25 pmPSP - ORD
1 stop9h 45mMultiple Airlines
Wed 7/26:00 amORD - PSP
1 stop9h 15mMultiple Airlines
Deal found 4/10$299
This Southwest deal was found by Cheapflights users on 4/10. 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 5/103:55 pmPSP - ORD
1 stop5h 45mSouthwest
Sat 5/176:15 amORD - PSP
1 stop6h 15mSouthwest
Deal found 4/10$301

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 April 11, 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

Sat 5/3

5:20 am-1:15 pm

1 stop5h 55m

Chicago O'Hare Intl

Sat 5/17

9:30 am-12:09 pm

Nonstop4h 39m

$241

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 4/30

8:20 am-6:20 pm

1 stop8h 00m

Chicago O'Hare Intl

Sat 5/3

12:00 pm-6:17 pm

1 stop8h 17m

$246

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Sat 5/3

1:57 pm-7:56 pm

Nonstop3h 59m

Chicago O'Hare Intl

Sat 5/17

10:05 am-12:29 pm

Nonstop4h 24m

$250

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 6/3

12:24 pm-9:40 pm

1 stop7h 16m

Chicago O'Hare Intl

Wed 6/4

7:30 am-11:44 am

1 stop6h 14m

$257

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 5/3

12:30 pm-10:22 pm

1 stop7h 52m

Chicago Midway

Sat 5/17

6:00 am-4:28 pm

2 stops12h 28m

$262

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Sat 5/3

8:20 am-7:10 pm

1 stop8h 50m

Chicago O'Hare Intl

Mon 5/5

6:00 am-1:12 pm

1 stop9h 12m

$269

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Fri 5/23

11:57 am-11:52 pm

1 stop9h 55m

Chicago O'Hare Intl

Mon 5/26

6:00 am-11:12 am

1 stop7h 12m

$270

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Thu 4/24

6:10 pm-1:23 pm

1 stop17h 13m

Chicago O'Hare Intl

Sun 4/27

8:15 am-5:04 pm

1 stop10h 49m

$275

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 6/3

6:14 pm-5:40 am

1 stop9h 26m

Chicago O'Hare Intl

Fri 6/6

6:00 am-11:09 am

1 stop7h 09m

$280

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Thu 8/7

3:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

Wed 8/20

2:15 pm-8:55 pm

1 stop8h 40m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 22 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
MytripPrice Accuracy3 starsTrust 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 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 flight deals on Cheapflights vs. FlightHub >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 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 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 April 4, 2025.

Booking 42 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, August is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $245). Flying from Palm Springs to Chicago in March is currently the most expensive (average of $321). 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 April 11, 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 36% 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 Wednesday at noon when fares are most often at their lowest. Sunday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Palm Springs to Chicago

Explore weekly flight availability from Palm Springs to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 11, 2025.

The most flights from PSP to CHI are scheduled on a Thursday (10 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 11, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Palm Springs to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,851 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,279 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,910 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Hawaiian Airlines
7.9
Good
2,366 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,636 reviews
Alaska Airlines
8.0
Very good
9,851 reviews

Food

7.1

Boarding

8.2

Overall

8.0

Comfort

7.9

Crew

8.5

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 6 outbound flights to Chicago per day from 4 airlines. Palm Springs is conveniently located just 2.2 mi from Palm Springs’s city center.

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

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $241. Additional round-trip tickets that might be worth considering are offered by Alaska Airlines and American Airlines, with the lowest prices starting at $246 and $250, respectively. These flights start at 43% 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 Sun Country Air, which is currently one of the cheapest options available, starting at $153. Southwest flights start at $155 while deals on Frontier start at $156 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 (91%), American Airlines (89%), United Airlines( 88%).

  • 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 $1,003, our data indicates the cheapest price to be $152. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $249.

  • 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, August is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $245). Flying from Palm Springs to Chicago in March is currently the most expensive (average of $321). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 April 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$283Average$373FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$295Average$430FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$315Average$438FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$317Average$453FlexibilityNo cancel feeOn-time69%

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