PSP - CHI

$136 Find Cheap Flights from Palm Springs to Chicago - Compare and Save

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 1/20. 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

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Everything you should know

Cheapest round-trip
$251
Typical prices: $320-$410
United Airlines
Wed 11/4Wed 11/11
PSP - ORD • Non-stop
Cheapest one-way
$136
Southwest
Wed 1/20
PSP - MDW • 1 stop
Top airlines
Cheapest • from $251 (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 United Airlines. Average duration is 0
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 34% average savings
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $239 (round-trip)
Shortest trip • 6h 07m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 20% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
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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, Nov 4 - Wed, Nov 11
United Airlines Logo
10:54 am - 4:55 pm
PSP
-
ORD
4h 01mnonstop
United Airlines Logo
9:05 am - 11:42 am
ORD
-
PSP
4h 37mnonstop
$251United Airlines
Tue, Dec 1 - Sat, Dec 5
American Airlines Logo
12:43 pm - 6:55 pm
PSP
-
ORD
4h 12mnonstop
American Airlines Logo
9:50 am - 12:18 pm
ORD
-
PSP
4h 28mnonstop
$261American Airlines
Wed, Oct 21 - Sat, Oct 24
United Airlines Logo
10:30 am - 4:32 pm
PSP
-
ORD
4h 02mnonstop
United Airlines Logo
6:07 am - 2:19 pm
ORD
-
PSP
10h 12m
1 stop
$267United Airlines
Sat, Sep 5 - Tue, Sep 8
United Airlines Logo
5:20 am - 1:30 pm
PSP
-
ORD
6h 10m
1 stop
United Airlines Logo
6:00 am - 12:31 pm
ORD
-
PSP
8h 31m
1 stop
$271United Airlines
Thu, Sep 17 - Sat, Sep 26
Southwest Logo
4:00 pm - 12:25 am
PSP
-
MDW
6h 25m
1 stop
Southwest Logo
5:05 pm - 8:55 pm
MDW
-
PSP
5h 50m
1 stop
$274Southwest
Sat, Sep 5 - Tue, Sep 8
Southwest Logo
7:20 am - 7:10 pm
PSP
-
MDW
9h 50m
2 stops
Southwest Logo
6:00 pm - 9:55 pm
MDW
-
PSP
5h 55m
1 stop
$276Southwest
Tue, Oct 6 - Wed, Oct 7
Southwest Logo
12:05 pm - 9:00 pm
PSP
-
MDW
6h 55m
1 stop
Southwest Logo
6:05 am - 10:15 am
MDW
-
PSP
6h 10m
1 stop
$277Southwest
Tue, Aug 18 - Tue, Aug 25
Southwest Logo
5:30 pm - 5:40 am
PSP
-
MDW
10h 10m
2 stops
Southwest Logo
3:50 pm - 9:55 pm
MDW
-
PSP
8h 05m
1 stop
$279Southwest
Tue, Sep 1 - Sat, Sep 5
Delta Logo
12:30 pm - 9:33 pm
PSP
-
ORD
7h 03m
1 stop
Delta Logo
4:45 pm - 9:30 pm
ORD
-
PSP
6h 45m
1 stop
$281Delta
Sat, Sep 5 - Sun, Sep 6
Delta Logo
12:30 pm - 9:33 pm
PSP
-
ORD
7h 03m
1 stop
Delta Logo
6:00 am - 11:48 am
ORD
-
PSP
7h 48m
2 stops
$286Delta
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.

How much is a round-trip flight from Palm Springs to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Palm Springs to Chicago departing in November.

Flight prices are below average for this route right now.

Flights to Chicago from Palm Springs usually cost between $293 and $541 in November.
The lowest price found in the past 5 days was $251 on United Airlines (Nov 4-Nov 11).

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 $238 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, 34% 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 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 October, where tickets cost $326 (return) on average. On the other hand, the most expensive months are June and July, where the average cost of round-trip tickets is $484 and $448 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.

No, with an average price for the route of $434, prices are generally cheapest when you fly direct.

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, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 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 season

January

Cheapest flight

$136
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly and prices are also 19% lower on average.
Flight from Palm Springs to Chicago Midway 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 5 days, the lowest price for a flight from Palm Springs to Chicago was $136 for a one-way ticket and $251 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, 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.

  • 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 $443 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 $304 and an overall rating of 7.8.

  • 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 $237 or less one-way and $410 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

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United Airlines

United Airlines

See more direct flights

Direct returns

Chicago to Palm Springs

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

United Airlines

United Airlines

Sunday

United 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 4233 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

2.0 MediocreMatthew, Jun 2026
CVG - MDW
Read more Southwest reviews

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

If your boarding Military, it should be with ore board, and with my spouse, so rude and stupid to not let us board together and before a group. All the other airlines clearly understand Military courtesy, this is why I Rarely fly SWA and Always fly Alaska

Flight was ok. Boarding wasn’t fun. Flights were delayed by 12 minutes on each leg.

Wifi didn’t work, no service, seats are hard as rocks

It was as good as it could be. Flying is not a pleasant experience these days.

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

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

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

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

5 hour delay. They blamed the weather but it was the computer issues they had been dealing with for days.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

Plane was late because of a mechanical malfunction and the food listed as available was not. Flight attendants seem over worked and under paid. They just done seem happy. And that can be seen in their faces.

The captain was amazing and kept us informed throughout that there would be some rough air. The flight also got delayed but we were able to actually leave on time, which was great.

I love the free entertainment. It makes the trip go by quickly. I also love that the flight was not 100% full. There was a seat open in the middle. I hate traveling on flights that are jam packed and they are asking people to give up their seats or the overhead bins are full and you have to check your bag. It just makes the flight difficult. Thanks Delta!

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

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.

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.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

when you can say you don't remember being at any point upset during a flight, the airline is winning .

I had a great flight. Everything went smoothly and the flight arrived early.

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Wifi did not work. Cut off on and off every 10 min

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

The flight from LA to Chicago was smooth and service was very good overall.

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

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.

Was not able to watch most shows on the entertainment site. They would not load

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

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?

It was nice being on a flight that had working wifi. The boarding was quick - why don’t all airlines have small boarding groups window to aisle? Makes so much sense!!! I was disappointed to be the first person stopped to have to gate check my carryon. Especially when there was plenty of overhead space at the back! But I get it…keeps it moving. Crew was nice.

The flight encountered a delay exceeding 4 hours. The food voucher issued was valued at $12, insufficient to cover our meal expenses. Consequently, I was unable to take my medication, leading to a drop in blood sugar levels and exacerbating my anxiety.

On time! Cabin crew attentive. Good WiFi sofrtvterm free internet appreciated

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

Information on your arrival and departure airports