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$68+ 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 10/10. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in August or May, booked 86 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

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 septiembre 11, 2025.

Round-trip from

$127
(Trip.com)

One-way from

$68
(Kiwi.com)

Popular in

September

Cheapest in

August

Average price

$560

Good round-trip deal

$340 or less

Good one-way deal

$168 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 ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 septiembre 11, 2025.

This Trip.com deal was found by Cheapflights users on 9/9. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/312:41 pmPSP - ORD
1 stop9h 18mFrontier
lun. 10/66:10 amORD - PSP
1 stop7h 27mFrontier
Deal found 9/9$127
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/3111:52 amPSP - ORD
1 stop10h 24mFrontier
lun. 11/36:00 amORD - PSP
1 stop7h 07mFrontier
Deal found 9/9$129
This Frontier deal was found by Cheapflights users on 9/11. 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.
vie. 10/2412:00 pmPSP - ORD
1 stop10h 59mFrontier
lun. 10/276:50 amORD - PSP
1 stop6h 25mFrontier
Deal found 9/11$158
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 10/153:21 pmPSP - ORD
Nonstop4h 02mAmerican Airlines
mar. 10/217:24 amORD - PSP
Nonstop4h 24mAmerican Airlines
Deal found 9/10$163
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/411:03 amPSP - ORD
Nonstop4h 01mUnited Airlines
sáb. 10/119:30 amORD - PSP
Nonstop4h 17mUnited Airlines
Deal found 9/11$179
This American Airlines deal was found by Cheapflights users on 9/10. 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.
mié. 11/1911:47 amPSP - ORD
Nonstop3h 58mAmerican Airlines
dom. 11/238:49 pmORD - PSP
Nonstop4h 31mAmerican Airlines
Deal found 9/10$180
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/512:19 pmPSP - ORD
1 stop28h 15mFrontier
dom. 12/77:39 pmORD - PSP
1 stop17h 45mFrontier
Deal found 9/11$186
This Southwest deal was found by Cheapflights users on 9/10. 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.
jue. 11/64:25 pmPSP - MDW
1 stop5h 40mSouthwest
mar. 11/1112:20 pmMDW - PSP
1 stop6h 25mSouthwest
Deal found 9/10$187
This United Airlines deal was found by Cheapflights users on 9/9. 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. 10/911:03 amPSP - ORD
Nonstop4h 01mUnited Airlines
sáb. 10/119:30 amORD - PSP
Nonstop4h 17mUnited Airlines
Deal found 9/9$195
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/44:22 pmPSP - ORD
1 stop5h 37mUnited Airlines
dom. 12/79:11 amORD - PSP
Nonstop4h 31mUnited Airlines
Deal found 9/11$201
This Southwest deal was found by Cheapflights users on 9/10. 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.
mié. 11/55:30 amPSP - MDW
2 stops7h 30mSouthwest
mié. 11/1212:20 pmMDW - PSP
1 stop6h 25mSouthwest
Deal found 9/10$244
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/2211:45 amPSP - MDW
Nonstop3h 40mSouthwest
mar. 11/259:50 amMDW - PSP
Nonstop4h 20mSouthwest
Deal found 9/9$249

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 septiembre 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 - MDW

PSPMDW

Palm Springs

jue. 11/13

4:25 pm-12:05 am

1 stop5h 40m

Chicago Midway

mié. 11/19

12:20 pm-4:45 pm

1 stop6h 25m

$187

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

vie. 11/7

11:20 am-7:40 pm

1 stop6h 20m

Chicago O'Hare Intl

mié. 11/12

9:25 am-11:56 am

Nonstop4h 31m

$189

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mié. 11/5

9:00 am-4:58 pm

1 stop5h 58m

Chicago O'Hare Intl

mié. 11/12

9:25 am-11:56 am

Nonstop4h 31m

$189

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mié. 10/1

8:20 am-5:10 pm

1 stop6h 50m

Chicago O'Hare Intl

mié. 10/8

9:30 am-11:47 am

Nonstop4h 17m

$189

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

vie. 10/3

12:41 pm-11:59 pm

1 stop9h 18m

Chicago O'Hare Intl

dom. 10/5

5:35 am-12:29 pm

1 stop8h 54m

$193

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

jue. 10/9

11:03 am-5:04 pm

Nonstop4h 01m

Chicago O'Hare Intl

sáb. 10/11

4:25 pm-10:33 pm

1 stop8h 08m

$205

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

jue. 11/6

4:25 pm-12:05 am

1 stop5h 40m

Chicago Midway

mar. 11/11

8:25 am-4:45 pm

2 stops10h 20m

$207

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

jue. 11/6

8:34 am-6:50 pm

1 stop8h 16m

Chicago O'Hare Intl

mar. 11/11

8:47 am-12:46 pm

1 stop5h 59m

$215

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

mié. 11/5

5:30 am-3:00 pm

2 stops7h 30m

Chicago Midway

mié. 11/12

12:20 pm-4:45 pm

1 stop6h 25m

$244

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

sáb. 10/4

5:30 am-1:12 pm

1 stop5h 42m

Chicago O'Hare Intl

sáb. 10/11

2:53 pm-8:33 pm

1 stop7h 40m

$244

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 42 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 August 29, 2025.

Booking 86 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 septiembre 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 at noon, which can drop the price by up to 19% 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 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.

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 septiembre 11, 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
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

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 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.

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

    Southwest, United Airlines, and Frontier can get you from Palm Springs to Chicago in just under 5h 40m. Your travel time can differ by up to 3h 38m. 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 $255, respectively. These flights start at 56% lower than the current average price 3 months from now.

  • 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 $347, our data indicates the cheapest price to be $115. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $179.

  • 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 Chicago?

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

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Alternative routes for Palm Springs to Chicago

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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$179Average$297FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$250Average$393FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$255Average$400FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$310Average$455FlexibilityNo cancel feeOn-time69%

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