PSP - CHI

$105 Find Cheap Flights from Palm Springs to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Palm Springs to Chicago departing on 10/31. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Palm Springs to Chicago (PSP-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Palm Springs to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Palm Springs to Chicago

Sun, Aug 31 - Thu, Sep 4
Alaska Airlines Logo
7:05 am - 5:00 amPSP-ORD
19h 55m1 stop
Alaska Airlines Logo
2:07 pm - 8:07 pmORD-PSP
8h 00m1 stop
$248Alaska Airlines
Find Deal
Mon, Aug 11 - Mon, Aug 18
Frontier Logo
12:02 pm - 12:10 amPSP-ORD
10h 08m1 stop
Frontier Logo
5:40 am - 11:00 amORD-PSP
7h 20m1 stop
$255Frontier
Find Deal
Mon, Jun 30 - Fri, Jul 4
Southwest Logo
10:45 am - 9:15 pmPSP-MDW
8h 30m1 stop
Southwest Logo
3:05 pm - 7:45 pmMDW-PSP
6h 40m1 stop
$259Southwest
Find Deal
Sun, Aug 31 - Tue, Sep 9
Delta Logo
12:20 pm - 10:04 pmPSP-ORD
7h 44m1 stop
Delta Logo
7:45 am - 11:36 amORD-PSP
5h 51m1 stop
$268Delta
Find Deal
Sun, Aug 31 - Tue, Sep 9
Delta Logo
12:20 pm - 10:04 pmPSP-ORD
7h 44m1 stop
Delta Logo
6:10 am - 11:36 amORD-PSP
7h 26m2 stops
$273Delta
Find Deal
Mon, Oct 6 - Sat, Oct 11
American Airlines Logo
1:44 pm - 7:45 pmPSP-ORD
4h 01mnonstop
American Airlines Logo
8:05 am - 10:22 amORD-PSP
4h 17mnonstop
$278American Airlines
Find Deal
Mon, Oct 6 - Sat, Oct 11
American Airlines Logo
3:08 pm - 11:46 pmPSP-ORD
6h 38m1 stop
American Airlines Logo
8:05 am - 10:22 amORD-PSP
4h 17mnonstop
$288American Airlines
Find Deal
Tue, Jul 8 - Wed, Jul 16
Southwest Logo
5:50 am - 1:50 pmPSP-MDW
6h 00m1 stop
Southwest Logo
5:55 pm - 10:55 pmMDW-PSP
7h 00m1 stop
$289Southwest
Find Deal
Thu, Sep 18 - Fri, Sep 26
United Airlines Logo
8:35 am - 6:53 pmPSP-ORD
8h 18m1 stop
United Airlines Logo
9:30 am - 11:47 amORD-PSP
4h 17mnonstop
$340United Airlines
Find Deal
Thu, Jul 17 - Wed, Jul 23
United Airlines Logo
6:30 pm - 5:18 amPSP-ORD
8h 48m1 stop
United Airlines Logo
7:10 am - 12:33 pmORD-PSP
7h 23m1 stop
$379United Airlines
Find Deal
Expert advice

Expert advice for your flight from Palm Springs to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
American Airlines

Consider Main Cabin Extra for early boarding and complimentary drinks on longer flights.


Download the American Airlines app for access to inflight entertainment without seatback screens.

United Airlines

Opt for Economy Plus for up to six inches more legroom than standard economy seats.


Check United's Wi-Fi coverage map before purchasing Wi-Fi for consistent connectivity.

Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Useful Info

KAYAK's insights & trends for Palm Springs to Chicago flights

Get data-powered insights and trends into flights from Palm Springs to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Palm Springs to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Palm Springs to Chicago.

Our data shows that the cheapest route for a return flight from Palm Springs to Chicago cost $264 and was between Palm Springs (PSP) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $264.

What’s the cheapest day of the week to fly from Palm Springs to Chicago?

The average price of all round-trip flights from Palm Springs to Chicago clicked on KAYAK for each day over the last 12 months.

For Palm Springs to Chicago, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago back to Palm Springs, the best deals are generally found on Monday, with Thursday being the most expensive.

What is the cheapest month to fly from Palm Springs to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Palm Springs to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Palm Springs to Chicago is May, where tickets cost $348 (return) on average. On the other hand, the most expensive months are July and April, where the average cost of round-trip tickets is $534 and $500 respectively.

Can I save money by flying with a layover from Palm Springs to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $1,138 on average.

How far in advance should I book a flight from Palm Springs to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Palm Springs to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Palm Springs to Chicago, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonMarch
High seasonMay
Cheapest flight$105
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Palm Springs to Chicago O'Hare Airport

When to book flights from Palm Springs to Chicago

Are your dates flexible? Find out the best times to travel from Palm Springs to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Palm Springs to Chicago

  • What is the cheapest flight from Palm Springs to Chicago?

    In the last 3 days, the lowest price for a flight from Palm Springs to Chicago was $105 for a one-way ticket and $248 for a round-trip.

  • Do I need a passport to fly between Palm Springs and Chicago?

    No, a passport isn't needed to fly from Palm Springs to Chicago. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Palm Springs to Chicago?

    Palm Springs is served by only 1 airport and there are 2 airports in Chicago. You will leave Palm Springs from Palm Springs and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Palm Springs to Chicago?

    All the following airlines offer inflight Wi-Fi service on the Palm Springs to Chicago flight route: American Airlines, JetBlue, Alaska Airlines, Air Canada, Hawaiian Airlines, and Delta.

  • Which aircraft models fly most regularly from Palm Springs to Chicago?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Palm Springs to Chicago flight route.

  • Which airline alliances offer flights from Palm Springs to Chicago?

    oneworld, Star Alliance, and SkyTeam are the airline alliances operating flights between Palm Springs and Chicago, with oneworld being the most commonly used for this route.

  • Which is the best airline for flights from Palm Springs to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Palm Springs to Chicago are Southwest and Delta. With an average price for the route of $383 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $308 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Palm Springs to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Palm Springs to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Palm Springs to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Palm Springs is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Palm Springs to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Palm Springs with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Palm Springs to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Palm Springs up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Palm Springs to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $303 or less one-way and $398 or less round-trip.

Top 4 airlines serving from Palm Springs to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Palm Springs to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Palm Springs to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4287 reviews
7.1Food
8.2Boarding
8.0Comfort
7.6Entertainment
8.6Crew
Airline reviews

It was a perfect flight in all aspects! Both legs!

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

I liked the crew member who gave flight instructions on "in case of a problem:. The seats are so small that only a young teenager could sit in middle seat.

Great flight staff. Ease of boarding. Overall, very uneventful and easy trip.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

I actually received a notification from kayak on email but not one by text from Delta when my departure gait changed and I almost missed my flight

New boarding doesn't make sense. Filling front first is slow.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Everything you need to know for your flight from Palm Springs to Chicago

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