HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$100+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in August or May, booked 44 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 julio 29, 2025.

Round-trip from

$257
(Delta)

One-way from

$100
(Booking.com)

Popular in

September

Cheapest in

August

Average price

$424

Good round-trip deal

$310 or less

Good one-way deal

$246 or less
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 ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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

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 julio 29, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
mié. 8/2712:20 pmPSP - ORD
1 stop7h 44mDelta
dom. 8/317:45 amORD - PSP
1 stop5h 51mDelta
Deal found 7/29$257
This Frontier deal was found by Cheapflights users on 7/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2911:34 amPSP - ORD
1 stop10h 58mFrontier
lun. 9/86:00 amORD - PSP
1 stop7h 46mFrontier
Deal found 7/29$258
This American Airlines deal was found by Cheapflights users on 7/27. 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.
jue. 10/1610:41 amPSP - ORD
Nonstop4h 04mAmerican Airlines
sáb. 10/187:25 amORD - PSP
Nonstop4h 24mAmerican Airlines
Deal found 7/27$260
This Hawaiian Airlines deal was found by Cheapflights users on 7/28. 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 Hawaiian Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/162:07 pmPSP - ORD
1 stop7h 56mHawaiian Airlines
mar. 9/236:20 amORD - PSP
1 stop8h 53mHawaiian Airlines
Deal found 7/28$264
This Alaska Airlines deal was found by Cheapflights users on 7/29. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/302:07 pmPSP - ORD
1 stop7h 52mAlaska Airlines
vie. 9/52:07 pmORD - PSP
1 stop8h 00mAlaska Airlines
Deal found 7/29$268
This Delta deal was found by Cheapflights users on 7/28. 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.
mié. 12/246:00 amPSP - MDW
2 stops9h 37mDelta
mar. 1/66:00 amMDW - PSP
1 stop7h 34mDelta
Deal found 7/28$278
This Sun Country Air deal was found by Cheapflights users on 7/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/226:36 pmPSP - ORD
1 stop14h 03mSun Country Air
sáb. 11/2910:00 amORD - PSP
1 stop8h 30mSun Country Air
Deal found 7/27$282
This Southwest deal was found by Cheapflights users on 7/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 9/175:30 amPSP - MDW
1 stop8h 15mSouthwest
dom. 9/217:45 pmMDW - PSP
1 stop5h 50mSouthwest
Deal found 7/27$283
This United Airlines deal was found by Cheapflights users on 7/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 8/126:30 pmPSP - ORD
1 stop9h 45mUnited Airlines
mar. 8/268:49 amORD - PSP
1 stop5h 43mUnited Airlines
Deal found 7/28$295

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 julio 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

mié. 8/27

12:20 pm-10:04 pm

1 stop7h 44m

Chicago O'Hare Intl

dom. 8/31

7:45 am-11:36 am

1 stop5h 51m

$257

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

vie. 8/29

11:34 am-12:32 am

1 stop10h 58m

Chicago O'Hare Intl

dom. 9/7

6:00 am-11:46 am

1 stop7h 46m

$258

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

jue. 10/16

10:41 am-4:45 pm

Nonstop4h 04m

Chicago O'Hare Intl

sáb. 10/18

7:25 am-9:49 am

Nonstop4h 24m

$260

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mar. 9/16

2:07 pm-12:03 am

1 stop7h 56m

Chicago O'Hare Intl

mar. 9/23

6:20 am-1:13 pm

1 stop8h 53m

$264

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

sáb. 8/30

2:07 pm-11:59 pm

1 stop7h 52m

Chicago O'Hare Intl

vie. 9/5

2:07 pm-8:07 pm

1 stop8h 00m

$268

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

sáb. 11/22

6:36 pm-10:39 am

1 stop14h 03m

Chicago O'Hare Intl

sáb. 11/29

10:00 am-4:30 pm

1 stop8h 30m

$282

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

mié. 9/17

5:30 am-3:45 pm

1 stop8h 15m

Chicago Midway

dom. 9/21

7:45 pm-11:35 pm

1 stop5h 50m

$283

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

mar. 8/12

6:30 pm-6:15 am

1 stop9h 45m

Chicago O'Hare Intl

mar. 8/26

8:49 am-12:32 pm

1 stop5h 43m

$295

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

sáb. 8/23

6:10 am-6:37 pm

2 stops10h 27m

Chicago Midway

vie. 8/29

6:00 am-4:37 pm

2 stops12h 37m

$314

Palm SpringsChicago

PSP - ORD

PSPORD

Palm Springs

jue. 9/11

5:43 pm-8:18 am

1 stop12h 35m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 21 results
1
2
3

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 July 25, 2025.

Booking 33 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 julio 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 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 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.

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: 4h 50m.

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 julio 29, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

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

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

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
4,238 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

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
7,977 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Hawaiian Airlines
7.8
Good
2,605 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

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
8,899 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Comfort

7.8

Entertainment

7.1

Boarding

8.1

Food

7.1

Crew

8.5

Overall

8.0

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 5 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 Delta is currently your cheapest option to Chicago, with prices starting at $257. Additional round-trip tickets that might be worth considering are offered by Frontier and American Airlines, with the lowest prices starting at $258 and $260, respectively. These flights start at 38% 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 $100. American Airlines flights start at $115 while deals on United Airlines start at $121 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 $327, our data indicates the cheapest price to be $133. The most popular route (Palm Springs - Chicago O'Hare Intl), is priced around $254.

  • 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Palm Springs to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to O'Hare Intl flights
San Francisco to O'Hare Intl flights
Ontario to O'Hare Intl flights
Santa Ana to O'Hare Intl flights
San Francisco to Midway flights
Burbank to O'Hare Intl flights
San Jose to O'Hare Intl flights
San Diego to O'Hare Intl flights
Los Angeles to Midway flights
Oakland to O'Hare Intl flights
Las Vegas to O'Hare Intl flights
Sacramento to O'Hare Intl flights
San Francisco to St. Louis flights
Los Angeles to St. Louis flights
San Jose to Midway flights
Fresno to O'Hare Intl flights
San Diego to Midway flights
Ontario to Midway flights
Oakland to Midway flights
Las Vegas to Midway flights
Santa Ana to Midway flights
Long Beach to O'Hare Intl flights
Reno to O'Hare Intl flights
Ontario to St. Louis flights
Burbank to Midway flights
San Diego to Moline flights
Palm Springs to O'Hare Intl flights
Sacramento to Midway flights
San Diego to St. Louis flights
Monterey to O'Hare Intl flights
Las Vegas to St. Louis flights
San Diego to Peoria flights
Reno to Midway flights
Fresno to Midway flights
San Jose to St. Louis flights
Sacramento to St. Louis flights
San Francisco to Moline flights
Oakland to St. Louis flights
Santa Barbara to O'Hare Intl flights
Burbank to St. Louis flights
Reno to St. Louis flights
Long Beach to Midway flights
Palm Springs to Midway flights
Santa Rosa to O'Hare Intl flights
Los Angeles to Rockford flights
Santa Ana to St. Louis flights
Bakersfield to O'Hare Intl flights
Santa Barbara to St. Louis flights
Los Angeles to Peoria flights
Medford to O'Hare Intl flights

Top 5 airlines flying from Palm Springs to Chicago

Discover the top 5 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 julio 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$248Average$297FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$250Average$398FlexibilityNo cancel feeOn-time63%
Alaska AirlinesCheapest$256Average$293FlexibilityNo cancel feeOn-time75%
American AirlinesCheapest$261Average$405FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$312Average$450FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.