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$105+ 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 10/31. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$248
(Alaska Airlines)

One-way from

$110
(United Airlines)

Popular in

July

Cheapest in

May

Average price

$388

Good round-trip deal

$398 or less

Good one-way deal

$214 or less
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. 1% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Palm Springs to Chicago (CHI).
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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 junio 12, 2025.

This Alaska Airlines deal was found by Cheapflights users on 6/10. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/317:05 amPSP - ORD
1 stop19h 55mAlaska Airlines
jue. 9/42:07 pmORD - PSP
1 stop8h 00mAlaska Airlines
Deal found 6/10$248
This Frontier deal was found by Cheapflights users on 6/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/1112:02 pmPSP - ORD
1 stop10h 08mFrontier
lun. 8/185:40 amORD - PSP
1 stop7h 20mFrontier
Deal found 6/11$255
This Southwest deal was found by Cheapflights users on 6/10. 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.
lun. 6/3010:45 amPSP - MDW
1 stop8h 30mSouthwest
vie. 7/43:05 pmMDW - PSP
1 stop6h 40mSouthwest
Deal found 6/10$259
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/3112:20 pmPSP - ORD
1 stop7h 44mDelta
mar. 9/97:45 amORD - PSP
1 stop5h 51mDelta
Deal found 6/11$268
This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 10/61:44 pmPSP - ORD
Nonstop4h 01mAmerican Airlines
sáb. 10/118:05 amORD - PSP
Nonstop4h 17mAmerican Airlines
Deal found 6/11$278
This Delta deal was found by Cheapflights users on 6/12. 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.
mar. 7/85:13 pmPSP - MDW
2 stops13h 31mDelta
mié. 7/1610:30 amMDW - PSP
2 stops12h 56mDelta
Deal found 6/12$299
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/74:00 pmPSP - ORD
1 stop5h 40mSouthwest
jue. 7/105:25 pmORD - PSP
1 stop7h 30mSouthwest
Deal found 6/11$314
This Sun Country Air deal was found by Cheapflights users on 6/10. 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.
mié. 11/265:36 pmPSP - ORD
1 stop12h 44mSun Country Air
dom. 11/307:52 pmORD - PSP
1 stop22h 38mSun Country Air
Deal found 6/10$335
This United Airlines deal was found by Cheapflights users on 6/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/188:35 amPSP - ORD
1 stop8h 18mUnited Airlines
vie. 9/269:30 amORD - PSP
Nonstop4h 17mUnited Airlines
Deal found 6/9$340
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/1211:55 amPSP - MDW
1 stop8h 43mFrontier
dom. 9/147:56 pmMDW - PSP
1 stop17h 14mFrontier
Deal found 6/10$372
This Hawaiian Airlines deal was found by Cheapflights users on 6/10. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/159:10 amPSP - ORD
1 stop7h 08mHawaiian Airlines
dom. 7/206:00 amORD - PSP
1 stop9h 15mHawaiian Airlines
Deal found 6/10$408

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 junio 12, 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

dom. 8/31

7:05 am-5:00 am

1 stop19h 55m

Chicago O'Hare Intl

jue. 9/4

2:07 pm-8:07 pm

1 stop8h 00m

$248

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

lun. 8/11

12:02 pm-12:10 am

1 stop10h 08m

Chicago O'Hare Intl

lun. 8/18

5:40 am-11:00 am

1 stop7h 20m

$255

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

lun. 6/30

10:45 am-9:15 pm

1 stop8h 30m

Chicago Midway

vie. 7/4

3:05 pm-7:45 pm

1 stop6h 40m

$259

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

dom. 8/31

12:20 pm-10:04 pm

1 stop7h 44m

Chicago O'Hare Intl

mar. 9/9

7:45 am-11:36 am

1 stop5h 51m

$268

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

lun. 10/6

1:44 pm-7:45 pm

Nonstop4h 01m

Chicago O'Hare Intl

sáb. 10/11

8:05 am-10:22 am

Nonstop4h 17m

$278

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

lun. 7/21

5:13 pm-8:44 am

2 stops13h 31m

Chicago Midway

mar. 7/29

9:24 am-9:26 pm

2 stops14h 02m

$319

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mié. 11/26

5:36 pm-8:20 am

1 stop12h 44m

Chicago O'Hare Intl

dom. 11/30

7:52 pm-4:30 pm

1 stop22h 38m

$335

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mar. 7/8

5:50 am-3:20 pm

1 stop7h 30m

Chicago O'Hare Intl

mié. 7/16

1:30 pm-10:55 pm

2 stops11h 25m

$336

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

jue. 9/18

8:35 am-6:53 pm

1 stop8h 18m

Chicago O'Hare Intl

vie. 9/26

9:30 am-11:47 am

Nonstop4h 17m

$340

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

vie. 9/12

11:55 am-10:38 pm

1 stop8h 43m

Chicago Midway

dom. 9/14

7:56 pm-11:10 am

1 stop17h 14m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 24 results
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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 June 9, 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 junio 12, 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 Saturday at noon 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.

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 junio 12, 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
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.9
Good
2,494 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 0 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 Alaska Airlines is currently your cheapest option to Chicago, with prices starting at $248. Additional round-trip tickets that might be worth considering are offered by Frontier and Southwest, with the lowest prices starting at $255 and $259, respectively. These flights start at 41% 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 $110. Southwest flights start at $115 while deals on Alaska Airlines start at $120 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 (94%), United Airlines (94%), Lufthansa( 94%).

  • 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 $641, our data indicates the cheapest price to be $112. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $273.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$344FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$256Average$420FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$265Average$408FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$311Average$448FlexibilityNo cancel feeOn-time69%

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