PSP - CHI

$161 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 5/12. 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, 0 bags

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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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$231
Overall average: $358
American Airlines
Mi 4/8Sa 4/11
PSP - ORD • Non-stop
Cheapest one-way
$161
Typical prices: $178-$342
Alaska Airlines
Di 5/12
PSP - ORD • 2 stops
Advice from real travelers
AI-powered summary based on content written by travel experts. AI can make mistakes.
Choose Economy Plus on United for extra legroom.
Use the American Airlines app for inflight entertainment.
Expert advice
Expert advice
Expert advice
Expert advice
Top airlines
Cheapest • from $231 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines, United Airlines and Southwest. Average duration is 3h 54m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 32% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $239 (round-trip)
Shortest trip • 5h 55m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 40% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 30% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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Flight Deals
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Expert advice
Flight 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

Mi, Apr 8 - Sa, Apr 11
American Airlines Logo
11:40 am - 5:46 pm
PSP
-
ORD
4h 06mnonstop
American Airlines Logo
9:14 pm - 11:29 pm
ORD
-
PSP
4h 15mnonstop
$231American Airlines
Mi, Mai 13 - Sa, Mai 16
United Airlines Logo
4:13 pm - 11:57 pm
PSP
-
ORD
5h 44m
1 stop
United Airlines Logo
9:25 am - 12:02 pm
ORD
-
PSP
4h 37mnonstop
$237United Airlines
Di, Apr 14 - Di, Apr 21
Southwest Logo
6:25 pm - 5:45 am
PSP
-
MDW
9h 20m
1 stop
Southwest Logo
10:20 am - 5:50 pm
MDW
-
PSP
9h 30m
1 stop
$251Southwest
Sa, Apr 25 - Sa, Mai 2
Southwest Logo
2:35 pm - 11:25 pm
PSP
-
ORD
6h 50m
1 stop
Southwest Logo
3:05 pm - 9:10 pm
ORD
-
PSP
8h 05m
1 stop
$251Southwest
Mi, Apr 8 - Sa, Apr 11
Southwest Logo
6:40 am - 4:35 pm
PSP
-
MDW
7h 55m
2 stops
Southwest Logo
2:40 pm - 7:00 pm
MDW
-
PSP
6h 20m
1 stop
$252Southwest
Di, Apr 14 - Di, Apr 21
Southwest Logo
6:40 am - 4:35 pm
PSP
-
MDW
7h 55m
2 stops
Southwest Logo
6:30 am - 10:15 am
MDW
-
PSP
5h 45m
1 stop
$256Southwest
Mi, Mai 13 - Di, Mai 19
Southwest Logo
10:55 am - 11:55 pm
PSP
-
ORD
11h 00m
2 stops
Southwest Logo
4:50 pm - 9:50 pm
ORD
-
PSP
7h 00m
1 stop
$256Southwest
Mi, Mai 13 - Di, Mai 19
United Airlines Logo
4:13 pm - 11:57 pm
PSP
-
ORD
5h 44m
1 stop
United Airlines Logo
9:25 am - 12:02 pm
ORD
-
PSP
4h 37mnonstop
$257United Airlines
Fr, Apr 10 - Di, Apr 14
American Airlines Logo
11:40 am - 5:46 pm
PSP
-
ORD
4h 06mnonstop
American Airlines Logo
8:25 am - 10:45 am
ORD
-
PSP
4h 20mnonstop
$260American Airlines
Mi, Apr 22 - So, Apr 26
Delta Logo
1:27 pm - 10:28 pm
PSP
-
MDW
7h 01m
1 stop
Delta Logo
6:00 am - 12:16 pm
MDW
-
PSP
8h 16m
1 stop
$280Delta
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Palm Springs to Chicago costs $250 on the route between Palm Springs (PSP) and Chicago O'Hare Intl Airport (ORD). Over the past month, this route was, on average, 32% cheaper than other Palm Springs-Chicago routes. It is also the most popular route.

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 Tuesday, with Sunday 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 August, where tickets cost $288 (return) on average. On the other hand, the most expensive months are March and September, where the average cost of round-trip tickets is $569 and $565 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 $379 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 3 weeks before departure, which saves you about 40% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Expert advice

Expert advice for your flight from Palm Springs to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Stefanie Waldek

Stefanie Waldek

Expert on United Airlines

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.

Good to know

Low seasonJanuary
Cheapest flight$161
Best time to beat the crowds but there is an average 32% increase in price.
Most popular time to fly with an average 37% increase in price.
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 $161 for a one-way ticket and $231 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?

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

  • 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?

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

  • On which days can I fly direct from Palm Springs to Chicago?

    There are nonstop flights from Palm Springs to Chicago on a daily basis.

  • 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 $355 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 $368 and an overall rating of 7.9.

  • 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 $260 or less one-way and $333 or less round-trip.

Prefer to fly direct from Palm Springs to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Palm Springs to Chicago.
Find which airlines fly direct from Palm Springs Airport to Chicago, which days they fly and book direct flights.

Direct departures

Palm Springs to Chicago

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Direct returns

Chicago to Palm Springs

Monday

American Airlines,United Airlines

American Airlines,United Airlines

Tuesday

American Airlines,United Airlines

American Airlines,United Airlines

Wednesday

American Airlines,United Airlines

American Airlines,United Airlines

Thursday

American Airlines,United Airlines

American Airlines,United Airlines

Friday

American Airlines,United Airlines

American Airlines,United Airlines

Saturday

American Airlines,Southwest,United Airlines

American Airlines,Southwest, +1 more

Sunday

American Airlines,United Airlines

American Airlines,United Airlines

See more direct flights

Reviews of the 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 4319 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
7.0Food
8.6Crew
Airline reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

WiFi was not working and didn’t have a beverage service

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Great flight but super high price. Glad it was a business trip and not personal

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

Got on the plane and sat there for an hour before departure.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

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

Information on your arrival and departure airports