$141 Find Cheap Flights from Chicago to Joshua Tree - 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 Chicago to Joshua Tree departing on 9/5. 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
$261
Typical prices: $289-$463
American Airlines
Tue 10/20Tue 10/27
ORD - PSP • Non-stop
Cheapest one-way
$141
Southwest
Sat 9/5
MDW - PSP • 1 stop
Arrival airport
You can't fly directly to Joshua Tree. It is served by Palm Springs (PSP), located 23.9 miles from Joshua Tree.
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Chicago to Joshua Tree (CHI-PSP)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Joshua Tree 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 Chicago to Joshua Tree

Tue, Oct 20 - Tue, Oct 27
American Airlines Logo
9:50 am - 12:18 pm
ORD
-
PSP
4h 28mnonstop
American Airlines Logo
12:43 pm - 6:50 pm
PSP
-
ORD
4h 07mnonstop
$261American Airlines
Sat, Dec 5 - Wed, Dec 9
American Airlines Logo
9:50 am - 12:18 pm
ORD
-
PSP
4h 28mnonstop
American Airlines Logo
12:43 pm - 6:50 pm
PSP
-
ORD
4h 07mnonstop
$261American Airlines
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
7:58 pm - 10:32 pm
ORD
-
PSP
4h 34mnonstop
United Airlines Logo
7:00 am - 1:05 pm
PSP
-
ORD
4h 05mnonstop
$261United Airlines
Sat, Oct 17 - Sat, Oct 24
United Airlines Logo
10:05 am - 12:33 pm
ORD
-
PSP
4h 28mnonstop
United Airlines Logo
10:25 am - 4:27 pm
PSP
-
ORD
4h 02mnonstop
$261United Airlines
Tue, Nov 3 - Tue, Nov 17
Southwest Logo
10:05 am - 4:50 pm
MDW
-
PSP
8h 45m
1 stop
Southwest Logo
7:00 am - 5:20 pm
PSP
-
MDW
8h 20m
1 stop
$281Southwest
Tue, Oct 20 - Tue, Oct 27
Southwest Logo
6:05 am - 10:10 am
MDW
-
PSP
6h 05m
1 stop
Southwest Logo
6:00 am - 1:25 pm
PSP
-
MDW
5h 25m
1 stop
$281Southwest
Sat, Jan 9 - Sat, Jan 16
Delta Logo
6:00 am - 11:23 am
MDW
-
PSP
7h 23m
1 stop
Delta Logo
12:40 pm - 10:10 pm
PSP
-
MDW
7h 30m
1 stop
$281Delta
Sat, Dec 5 - Wed, Dec 9
Delta Logo
6:00 am - 11:27 am
MDW
-
PSP
7h 27m
1 stop
Delta Logo
12:37 pm - 10:56 pm
PSP
-
MDW
8h 19m
1 stop
$281Delta
Sat, Nov 14 - Wed, Nov 18
Alaska Airlines Logo
9:31 am - 6:46 pm
ORD
-
PSP
11h 15m
1 stop
Alaska Airlines Logo
10:57 am - 11:57 pm
PSP
-
ORD
11h 00m
1 stop
$301Alaska Airlines
Fri, Sep 11 - Fri, Sep 18
Alaska Airlines Logo
3:52 pm - 11:08 pm
ORD
-
PSP
9h 16m
1 stop
Alaska Airlines Logo
2:08 pm - 11:59 pm
PSP
-
ORD
7h 51m
1 stop
$318Alaska Airlines
Useful Info

Good to know

Low season

August

Cheapest flight

$141
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Chicago Midway Airport to Palm Springs

When to book flights from Chicago to Joshua Tree

Are your dates flexible? Find out the best times to travel from Chicago to Joshua Tree based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

FAQs for booking flights from Chicago to Joshua Tree

  • Which airports will I be using when flying from Chicago to Joshua Tree?

    When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Joshua Tree does not have its own airport so you’ll be flying into nearby Palm Springs airport, which is 23.9 mi away.

  • What’s the cheapest day of the week to fly between Chicago and Joshua Tree?

    Consider leaving on a Friday and avoid Saturdays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Fridays and the most expensive ones on Wednesdays.

  • How does KAYAK find such low prices on flights from Chicago to Joshua Tree?

    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 Chicago to Joshua Tree.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Joshua Tree from Chicago 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 Chicago to Joshua Tree?

    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 Joshua Tree with an airline and back to Chicago with another airline.

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

    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 Joshua Tree from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Chicago to Joshua Tree?

    In the last 5 days, the cheapest one-way ticket between Chicago and Joshua Tree found on KAYAK was with Southwest for $125. United Airlines offered a round-trip connection from $234 and American Airlines from $259.

Top tips for finding cheap flights from Chicago to Joshua Tree

  • There is no airport in Joshua Tree. Instead, you’ll be flying into Palm Springs Airport when flying between Chicago and Joshua Tree.
  • The cheapest flight from Chicago to Joshua Tree was found 65 days before departure, on average.
  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be June, July and August. The cheapest month to fly is January.

Reviews of the top 4 airlines serving Chicago to Joshua Tree

 
Need help choosing which airline to fly with from Chicago to Joshua Tree? 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 4229 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

10.0 ExcellentDenis, Aug 2026
MDW - ATL
Read more Southwest reviews

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Overall good, just screaming kids in the area the whole flight.

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Flight was delayed more than 2 hour do the scheduling issues and then some confusing weight and balance matters, followed by a miscommunication with the tower on which runway was going to be used based on the airplane weight. All these things should have been figured out in advance. Instead of arriving at 12:30 a.m. we arrived at 2:30 a.m. very difficult to find a taxi or other transport at SFO. Luggage was delayed. An extension of an unpleasant flight day

no entertainment options available on a 4+ hour flight. packed in like sardines. one bathroom. late flight.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

Very easy to use and convenient, you can perform any action within the same portal

Okay considering we had weather delays which the Pilot notified us of immediately!

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Stop changing gates. Stop cancelling flights Stop moving my seat.

The staff was frielndly. The plane was terrible, it was too small and should be decommissioned. There were no back seat screens at all. The only beverages we had a choice from was coffee, tea or water. The only bathroom in the back was behind the flight attendant's jump seat and wasn't working. And I literally felt like I was sitting on top of the guy next to me. It was terribly hot in the plane and we had to sit on the tarmac in Chicago for 1/2 hour due to congestion in Mpls. Wouldn't they have know that before they even boarded us so that we could have sat in comfort in the terminal?

This was one of the worst flights I’ve been on in years. I upgraded to comfort and had such an uncomfortable experience. The person next to me was oversized - which I understand - however, they took up their space and mine. I could only use about 50% of my seat space to not be physically touching this person the entire flight and there was no spatial awareness. I also could not use the seat outlet because their body was obstructing it. It was very inconvenient. Their body kept touching me repeatedly during the flight and I felt very uncomfortable. To pay more for an upgraded space and then not even being able to use it was highly disappointing.

It was very cold because the air conditioner was on high power, and my son got sick.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Terrible, if possible won't be flying again anytime soon!

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

A bit rush for transit. Food and entertainment are not available

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Boarding was a mess - the agent basically called every group in rapid succession, so there was no organization at all. The economy seats are a joke, and main cabin extra seats were sold out when I purchased my flight. As such, I was locked in the same position for four hours. Being 6’6”, it was impossible to get my bag out from under the seat in front of me, and I couldn’t have used my laptop even if my bag were accessible due to the minuscule seat pitch. Also the wifi was broken. American is a joke - can’t wait until they merge with Spirit.

Horrible scam. Make you pay extra for more leg room then switch your seat as you’re boarding to a regular seat. Never fly American!

Everything you need to know for your flight from Chicago to Joshua Tree

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