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$167+ 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 6/11. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
Apr 24 — May 11
Fri 4/24
Fri 5/1
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

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in August or May, booked 33 days in advance, depart on a Wednesday or Thursday and return on a Tuesday

Cheap 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 March 25, 2026.

This Southwest deal was found by Cheapflights users on 3/25. 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.
Tue 5/126:10 am
PSP
-
ORD
1 stop5h 45m
Southwest
Tue 5/194:50 pm
ORD
-
PSP
1 stop7h 00m
Southwest
Deal found 3/25$183
This Southwest deal was found by Cheapflights users on 3/24. 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 5/1310:55 am
PSP
-
ORD
2 stops11h 00m
Southwest
Wed 5/2010:30 am
ORD
-
PSP
1 stop13h 00m
Southwest
Deal found 3/24$194
This Southwest deal was found by Cheapflights users on 3/24. 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.
Tue 5/56:10 am
PSP
-
MDW
2 stops8h 50m
Southwest
Sat 5/92:40 pm
MDW
-
PSP
1 stop6h 20m
Southwest
Deal found 3/24$200
This Southwest deal was found by Cheapflights users on 3/25. 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 4/256:50 am
PSP
-
MDW
1 stop5h 45m
Southwest
Sat 5/22:30 pm
MDW
-
PSP
1 stop6h 30m
Southwest
Deal found 3/25$211
This Southwest deal was found by Cheapflights users on 3/25. 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 4/256:05 am
PSP
-
ORD
1 stop6h 15m
Southwest
Sat 5/23:05 pm
ORD
-
PSP
1 stop8h 05m
Southwest
Deal found 3/25$216
This Southwest deal was found by Cheapflights users on 3/22. 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.
Tue 4/216:10 am
PSP
-
ORD
1 stop5h 45m
Southwest
Tue 4/284:50 pm
ORD
-
PSP
1 stop7h 00m
Southwest
Deal found 3/22$227
This Southwest deal was found by Cheapflights users on 3/24. 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 4/296:10 am
PSP
-
ORD
1 stop5h 45m
Southwest
Mon 5/44:50 pm
ORD
-
PSP
1 stop8h 10m
Southwest
Deal found 3/24$229
This Southwest deal was found by Cheapflights users on 3/24. 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 6/44:10 pm
PSP
-
MDW
1 stop7h 15m
Southwest
Tue 6/92:35 pm
MDW
-
PSP
2 stops9h 30m
Southwest
Deal found 3/24$234
This Delta deal was found by Cheapflights users on 3/23. 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.
Wed 4/221:53 pm
PSP
-
ORD
1 stop5h 25m
Delta
Wed 4/298:50 am
ORD
-
PSP
1 stop5h 59m
Delta
Deal found 3/23$237
This Southwest deal was found by Cheapflights users on 3/24. 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.
Mon 5/46:50 pm
PSP
-
MDW
1 stop9h 10m
Southwest
Sat 5/92:40 pm
MDW
-
PSP
1 stop6h 20m
Southwest
Deal found 3/24$241
This Delta deal was found by Cheapflights users on 3/25. 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 4/251:27 pm
PSP
-
MDW
1 stop7h 01m
Delta
Sat 5/25:40 am
MDW
-
PSP
1 stop8h 36m
Delta
Deal found 3/25$250
This Southwest deal was found by Cheapflights users on 3/24. 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 5/66:25 pm
PSP
-
MDW
1 stop9h 20m
Southwest
Sun 5/107:20 pm
MDW
-
PSP
1 stop6h 30m
Southwest
Deal found 3/24$266

Find 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 March 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$200
(Southwest)

One-way from

$167
(Southwest)

Popular in

September

Cheapest in

August

Average price

$526

Good round-trip deal

$327 or less

Good one-way deal

$250 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, 2% 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 March 2026
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 March 25, 2026.
Use the filters below to find and compare flights from Palm Springs to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 4/21

6:10 am-1:55 pm

1 stop5h 45m

Chicago O'Hare Intl

Tue 4/28

11:55 am-9:50 pm

2 stops11h 55m

$232

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 4/29

6:40 am-3:00 pm

1 stop6h 20m

Chicago O'Hare Intl

Sun 5/3

4:50 pm-11:50 pm

1 stop9h 00m

$266

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 4/22

1:27 pm-10:28 pm

1 stop7h 01m

Chicago Midway

Sun 4/26

6:00 am-12:16 pm

1 stop8h 16m

$293

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 4/21

6:10 am-2:10 pm

1 stop6h 00m

Chicago Midway

Tue 4/28

7:55 am-1:55 pm

1 stop8h 00m

$306

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 6/3

1:30 pm-9:39 pm

1 stop6h 09m

Chicago O'Hare Intl

Fri 6/12

4:30 pm-10:30 pm

1 stop8h 00m

$310

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Tue 4/28

1:27 pm-10:21 pm

1 stop6h 54m

Chicago O'Hare Intl

Sun 5/3

8:50 am-12:49 pm

1 stop5h 59m

$310

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

Wed 5/6

10:55 am-11:55 pm

2 stops11h 00m

Chicago O'Hare Intl

Fri 5/8

6:15 pm-10:15 pm

1 stop6h 00m

$315

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 5/16

6:05 am-5:15 pm

2 stops9h 10m

Chicago Midway

Wed 5/20

6:30 am-1:55 pm

2 stops9h 25m

$319

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 4/18

6:05 am-5:25 pm

2 stops9h 20m

Chicago Midway

Wed 4/22

4:00 pm-9:50 pm

2 stops7h 50m

$319

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 5/16

6:05 am-5:56 pm

2 stops9h 51m

Chicago Midway

Tue 5/19

9:23 am-4:28 pm

2 stops9h 05m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/20

Showing 1-10 of 36 resultsSorted by cheapest first
1
2
3
4

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 March 13, 2026.

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, April is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $97). Flying from Palm Springs to Chicago in March is currently the most expensive (average of $163). 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 March 25, 2026.

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 11% versus a flight in the morning.

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 March 23, 2026.

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. Sunday afternoons 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 March 25, 2026.

The most flights from PSP to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 on average).

How much does it cost to fly round-trip from Palm Springs to Chicago?

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 March 25, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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
4,332 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,332 reviews
Southwest
8.0
Very good
4,332 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,327 reviews
Southwest
8.0
Very good
4,332 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,478 reviews
Southwest
8.0
Very good
4,332 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.1
Good
11,493 reviews
Southwest
8.0
Very good
4,332 reviews

Comfort

8.0

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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 5 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, Delta, and Alaska Airlines can get you from Palm Springs to Chicago in just under 5h 45m. Your travel time can differ by up to 4h 54m. Palm Springs and Chicago are separated by a distance of 1647 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 $144. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $239 and $250, respectively. These flights start at 64% 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 Southwest, which is currently one of the cheapest options available, starting at $115. American Airlines flights start at $115 while deals on Frontier start at $124 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: Lufthansa (86%), Emirates (84%), United Airlines( 77%).

  • 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 $714, our data indicates the cheapest price to be $189. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $257.

  • 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, April is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $97). Flying from Palm Springs to Chicago in March is currently the most expensive (average of $163). 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
Lansing
Merrillville
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 March 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$144Average$288FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$239Average$374FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$250Average$368FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$259Average$386FlexibilityNo cancel feeOn-time69%

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