PSP - CHI

$116 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 2/28. 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: $368
United Airlines
Wed 2/18Sat 2/21
PSP - ORD • Non-stop
Cheapest one-way
$116
Typical prices: $219-$399
United Airlines
Sat 2/28
PSP - ORD • Non-stop
Our travelers' advice
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
United Airlines
Cheapest • from $231 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Top routes
PSP
-
ORD
Cheapest • 28% average savings
PSP
-
ORD
Most popular
Insights
Insights
Insights
Insights
When to book
3 weeks
in advance
Our data shows that travelers who book at least 3 weeks in advance save around 45% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
August
Cheapest • 29% price drop
September
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
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

Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
7:00 am - 12:54 pm
PSP
-
ORD
3h 54mnonstop
United Airlines Logo
3:45 pm - 6:16 pm
ORD
-
PSP
4h 31mnonstop
$231United Airlines
Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
4:14 pm - 11:59 pm
PSP
-
ORD
5h 45m
1 stop
United Airlines Logo
3:45 pm - 6:16 pm
ORD
-
PSP
4h 31mnonstop
$237United Airlines
Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
4:14 pm - 11:59 pm
PSP
-
ORD
5h 45m
1 stop
United Airlines Logo
4:00 pm - 9:54 pm
ORD
-
PSP
7h 54m
1 stop
$247United Airlines
Wed, Feb 18 - Sat, Feb 21
Delta Logo
5:10 pm - 8:38 am
PSP
-
ORD
13h 28m
2 stops
Delta Logo
5:25 am - 11:42 am
ORD
-
PSP
8h 17m
1 stop
$256Delta
Wed, Feb 18 - Sat, Feb 21
Southwest Logo
8:55 am - 5:15 pm
PSP
-
MDW
6h 20m
1 stop
Southwest Logo
8:15 am - 10:35 am
MDW
-
PSP
4h 20mnonstop
$260Southwest
Thu, Mar 5 - Sun, Mar 8
American Airlines Logo
6:05 am - 11:59 am
PSP
-
ORD
3h 54mnonstop
American Airlines Logo
9:00 pm - 11:23 pm
ORD
-
PSP
4h 23mnonstop
$269American Airlines
Wed, Feb 18 - Sat, Feb 21
Southwest Logo
8:55 am - 5:15 pm
PSP
-
MDW
6h 20m
1 stop
Southwest Logo
3:15 pm - 10:00 pm
MDW
-
PSP
8h 45m
1 stop
$270Southwest
Sat, Feb 28 - Mon, Mar 2
Alaska Airlines Logo
8:29 am - 11:56 pm
PSP
-
ORD
13h 27m
1 stop
Alaska Airlines Logo
1:00 pm - 10:25 pm
ORD
-
PSP
11h 25m
1 stop
$270Alaska Airlines
Wed, Feb 25 - Wed, Mar 4
American Airlines Logo
2:10 pm - 8:05 pm
PSP
-
ORD
3h 55mnonstop
American Airlines Logo
9:03 pm - 11:26 pm
ORD
-
PSP
4h 23mnonstop
$282American Airlines
Wed, Apr 22 - Sun, Apr 26
Delta Logo
1:28 pm - 10:28 pm
PSP
-
MDW
7h 00m
1 stop
Delta Logo
6:00 am - 12:16 pm
MDW
-
PSP
8h 16m
1 stop
$289Delta
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 absolute cheapest return flight from Palm Springs to Chicago costs $269 on the route between Palm Springs (PSP) and Chicago O'Hare Intl Airport (ORD). However, over the past month, flights between Palm Springs (PSP) and Chicago Midway Airport (MDW) were, on average, 28% cheaper than other Palm Springs-Chicago routes. The most popular route is between Palm Springs (PSP) and Chicago O'Hare Intl Airport (ORD).

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 Sunday is the most expensive. Flying from Chicago back to Palm Springs, the best deals are generally found on Tuesday, 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 August, where tickets cost $288 (return) on average. On the other hand, the most expensive months are September and January, where the average cost of round-trip tickets is $563 and $544 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 2 stops layover the cheapest option at $297 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 45% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 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 seasonNovember
Cheapest flight$116
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 38% 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 $116 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, Air Canada, and JetBlue 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 $363 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 $317 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 $224 or less one-way and $372 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 4267 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

Cramped seating for me. Luckily it wasn’t a long flight

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

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Information on your arrival and departure airports