$107+ Cheap flights from Palm Springs (PSP) to Chicago (CHI)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
PSP — CHI
Nov 10 — Nov 171
Round-trip
1 adult, Economy
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Find cheap flights from Palm Springs to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from Palm Springs to Chicago are usually found in April or March, booked 34 days in advance, depart on a Wednesday or Saturday and return on a Tuesday
Cheap flight deals from Palm Springs to Chicago
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Cheapest flights from Palm Springs to ChicagoExplore the most affordable flight options available from Palm Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 11, 2026.
Explore the most affordable flight options available from Palm Springs to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 11, 2026.
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:05 pm -
1 stop8h 40m
Tue 11/35:45 pm -
1 stop5h 50m
Deal found 10/8![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
2 stops8h 05m
Tue 11/101:20 pm -
2 stops9h 30m
Deal found 10/6![Southwest logo]()
$281
This American Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/812:56 pm -
Nonstop3h 54m
Wed 12/169:53 am -
Nonstop4h 31m
Deal found 10/10![American Airlines logo]()
$301
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1210:35 am -
Nonstop4h 03m
Tue 12/158:45 am -
1 stop7h 02m
Deal found 10/10![United Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1212:46 pm -
1 stop8h 08m
Tue 12/156:00 am -
1 stop7h 36m
Deal found 10/10![Delta logo]()
$321
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/512:24 pm -
1 stop7h 32m
Tue 12/155:30 am -
1 stop8h 06m
Deal found 10/10![Delta logo]()
$321
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/127:10 am -
2 stops7h 55m
Tue 12/155:45 pm -
1 stop5h 50m
Deal found 10/10![Southwest logo]()
$326
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:25 pm -
1 stop7h 34m
Wed 12/169:25 am -
Nonstop4h 38m
Deal found 10/10![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:00 pm -
1 stop6h 10m
Sun 11/156:05 pm -
1 stop7h 25m
Deal found 10/7![Southwest logo]()
$329
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:05 pm -
2 stops8h 40m
Tue 10/275:45 pm -
1 stop6h 00m
Deal found 10/6![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:10 pm -
1 stop9h 50m
Tue 11/35:45 pm -
1 stop5h 50m
Deal found 10/7![Southwest logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:10 am -
Nonstop4h 05m
Tue 11/107:56 pm -
Nonstop4h 34m
Deal found 10/6![United Airlines logo]()
$339
Best flights from Palm Springs to ChicagoDiscover carefully curated flight deals from Palm Springs to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 11, 2026.
Discover carefully curated flight deals from Palm Springs to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 11, 2026.
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/125:15 pm -
2 stops13h 34m
Tue 12/1512:34 pm -
2 stops11h 03m
Deal found 10/10![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:10 pm -
1 stop9h 50m
Tue 11/35:45 pm -
1 stop5h 50m
Deal found 10/7![Southwest logo]()
$334
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/27:00 am -
Nonstop4h 05m
Mon 12/71:57 pm -
1 stop8h 47m
Deal found 10/7![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/187:00 am -
2 stops8h 05m
Fri 11/205:40 pm -
2 stops7h 50m
Deal found 10/7![Southwest logo]()
$366
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:25 am -
Nonstop4h 03m
Mon 12/218:13 pm -
Nonstop4h 42m
Deal found 10/10![United Airlines logo]()
$379
This Delta deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/612:46 pm -
1 stop9h 10m
Tue 12/159:59 am -
2 stops13h 38m
Deal found 10/10![Delta logo]()
$395
This United Airlines deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/121:33 pm -
1 stop5h 57m
Mon 11/163:00 pm -
1 stop7h 05m
Deal found 10/10![United Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/183:05 pm -
1 stop7h 05m
Mon 12/216:00 am -
1 stop5h 55m
Deal found 10/9![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:12 pm -
2 stops13h 27m
Wed 10/282:03 pm -
1 stop9h 26m
Deal found 10/8![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/187:00 am -
Nonstop3h 59m
Mon 12/216:00 am -
1 stop6h 31m
Deal found 10/9![United Airlines logo]()
$383
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/134:00 pm -
1 stop6h 10m
Wed 12/161:20 pm -
2 stops10h 15m
Deal found 10/10![Southwest logo]()
$396
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:04 am -
2 stops8h 35m
Mon 11/231:31 pm -
2 stops10h 00m
Deal found 10/9![Delta logo]()
$411
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:33 pm -
1 stop6h 18m
Sat 10/248:45 am -
1 stop7h 34m
Deal found 10/6![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:40 pm -
1 stop7h 15m
Mon 11/235:20 pm -
2 stops7h 00m
Deal found 10/10![Southwest logo]()
$398
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/44:50 pm -
1 stop6h 09m
Sun 1/1012:40 pm -
1 stop6h 42m
Deal found 10/6![United Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:55 am -
2 stops7h 10m
Fri 10/236:25 pm -
1 stop5h 55m
Deal found 10/7![Southwest logo]()
$438
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/257:30 am -
1 stop7h 55m
Sat 1/25:55 am -
1 stop6h 00m
Deal found 10/6![Southwest logo]()
$479
This Southwest deal was found by Cheapflights users on 10/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:05 pm -
1 stop8h 45m
Sat 11/286:15 am -
1 stop6h 55m
Deal found 10/10![Southwest logo]()
$480
Last-minute flights from Palm Springs to ChicagoDiscover last-minute flight deals from Palm Springs to Chicago. Data last updated October 11, 2026 and is based on user searches.
Discover last-minute flight deals from Palm Springs to Chicago. Data last updated October 11, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2012:05 pm -
2 stops8h 40m
Tue 10/275:45 pm -
1 stop6h 00m
Deal found 10/6![Southwest logo]()
$333
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:05 am -
2 stops8h 55m
Wed 10/286:05 am -
1 stop6h 05m
Deal found 10/8![Southwest logo]()
$353
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/15:10 pm -
1 stop9h 50m
Tue 11/35:45 pm -
1 stop5h 50m
Deal found 10/7![Southwest logo]()
$334
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:05 pm -
1 stop8h 40m
Tue 11/35:45 pm -
1 stop5h 50m
Deal found 10/8![Southwest logo]()
$259
This Southwest deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am -
2 stops8h 05m
Tue 11/101:20 pm -
2 stops9h 30m
Deal found 10/6![Southwest logo]()
$281
This United Airlines deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:10 am -
Nonstop4h 05m
Tue 11/107:56 pm -
Nonstop4h 34m
Deal found 10/6![United Airlines logo]()
$339
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/124:00 pm -
1 stop6h 10m
Sun 11/156:05 pm -
1 stop7h 25m
Deal found 10/7![Southwest logo]()
$329
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:43 pm -
Nonstop4h 07m
Sat 11/215:09 pm -
1 stop7h 47m
Deal found 10/7![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:10 am -
Nonstop4h 05m
Sat 11/217:58 pm -
Nonstop4h 34m
Deal found 10/7![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1811:10 am -
1 stop11h 05m
Fri 11/206:05 pm -
1 stop7h 25m
Deal found 10/7![Southwest logo]()
$345
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:53 pm -
1 stop7h 06m
Fri 11/277:56 pm -
Nonstop4h 34m
Deal found 10/7![United Airlines logo]()
$350
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2510:26 am -
Nonstop4h 03m
Fri 11/277:56 pm -
Nonstop4h 34m
Deal found 10/7![United Airlines logo]()
$340
One-way flights from Palm Springs to ChicagoSearch for one-way flight options from Palm Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated October 11, 2026.
Search for one-way flight options from Palm Springs to Chicago. Find affordable one-way fares based on user searches. Data last updated October 11, 2026.
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/253:05 pm -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$107
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:10 am -
2 stops7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$112
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:05 pm -
1 stop8h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$130
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:00 am -
2 stops8h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$135
This Southwest deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/243:05 pm -
1 stop7h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Southwest logo]()
$158
This Southwest deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/1911:45 am -
1 stop7h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Southwest logo]()
$161
This Southwest deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/64:00 pm -
1 stop6h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/7![Southwest logo]()
$165
This Orbitz deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/910:00 am -
1 stop11h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![Alaska Airlines logo]()
$166
This Sun Country Air deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:48 pm -
1 stop20h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Sun Country Air logo]()
$168
This Kiwi.com deal was found by Cheapflights users on 10/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:36 pm -
2 stops28h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/6![Multiple Airlines logo]()
$173
This Sun Country Air deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:10 pm -
1 stop17h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/8![Sun Country Air logo]()
$188
This United Airlines deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/21:33 pm -
1 stop5h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/9![United Airlines logo]()
$189
Find flight deals from Palm Springs to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Palm Springs (PSP) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated October 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $259 (Southwest) |
One-way from | $107 (Southwest) |
Popular in | January |
Cheapest in | April |
Average price | $428 |
Good round-trip deal | $382 or less |
Good one-way deal | $310 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Palm Springs to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 11, 2026.
Use the filters below to find and compare flights from Palm Springs to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Wed 1/6
2:45 pm-10:30 pm
1 stop5h 45m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$107
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Sat 11/7
7:10 am-5:05 pm
2 stops7h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$112
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Tue 11/24
3:05 pm-12:15 am
1 stop7h 10m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$158
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Sat 12/19
11:45 am-9:40 pm
1 stop7h 55m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$161
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Tue 1/12
4:57 pm-11:51 am
2 stops16h 54m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$193
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Wed 1/13
12:40 pm-10:10 pm
1 stop7h 30m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Palm SpringsChicago
PSP Palm Springs - ORD Chicago O'Hare Intl
PSPORD
Palm Springs
Thu 1/7
6:00 am-3:27 pm
1 stop7h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Palm SpringsChicago
PSP Palm Springs - ORD Chicago O'Hare Intl
PSPORD
Palm Springs
Tue 12/8
12:46 pm-11:56 pm
1 stop9h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Quickest round-trip
Palm SpringsChicago
PSP Palm Springs - MDW Chicago Midway
PSPMDW
Palm Springs
Fri 12/11
2:40 pm-10:00 pm
1 stop5h 20m
Chicago Midway
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Palm SpringsChicago
PSP Palm Springs - ORD Chicago O'Hare Intl
PSPORD
Palm Springs
Fri 1/8
6:00 am-3:27 pm
1 stop7h 27m
Chicago O'Hare Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$194
Showing 1-10 of 37 resultsSorted by cheapest first
Compare providers for flights from Palm Springs to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Palm Springs to Chicago in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Palm Springs-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Palm Springs-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Palm Springs-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Palm Springs-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Palm Springs-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Palm Springs to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Palm Springs with our price prediction graph.
PSP-CHI
PSP-MDW
PSP-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Palm Springs to Chicago
PSP-CHI
PSP-MDW
PSP-ORD
What is the cheapest month to book a flight from Palm Springs to Chicago?
Currently, April is the cheapest month in which you can book a flight from Palm Springs to Chicago (average of $332). Flying from Palm Springs to Chicago in January is currently the most expensive (average of $484). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from PSP to CHI?
Find hourly flight availability from Palm Springs to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 11, 2026.
When flying from Palm Springs to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 9% versus a flight in the afternoon.
Weekly flight availability from Palm Springs to Chicago
Explore weekly flight availability from Palm Springs to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated October 11, 2026.
The most flights from PSP to CHI are scheduled on a Tuesday (4 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (2 on average).
How much does it cost to fly round-trip from Palm Springs to Chicago?
Airfare is below average for this route at the moment.
Palm Springs to Chicago flights typically cost between $370 and $551 in November.The cheapest round-trip price found within the last 5 days was $259 on Southwest (Nov 2-Nov 3).
How far ahead should I book a flight from Palm Springs to Chicago?
Booking 79 days in advance of your planned departure date is, on average, the best time to get cheap flights from Palm Springs to Chicago. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Palm Springs to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Palm Springs to Chicago. Price data was last updated on October 10, 2026.
Travelers seeking maximum savings on their Palm Springs to Chicago flight should consider departing on Monday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated October 11, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Palm Springs to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Food
7.0
Crew
8.6
Comfort
8.0
Boarding
8.1
Entertainment
7.4
Overall
7.9
Reviews
1 / 20
6.0
GoodReza,Jun 2026
TPA - MDW
Related info for your journey
Find useful and relevant information for your journey from Palm Springs to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter
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Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 11, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Palm Springs to Chicago by cabin class
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Palm Springs and Chicago flights
Browse other Palm Springs and Chicago flight options. Last updated on October 11, 2026.
Other flights from Palm Springs
Browse through other flights departing from Palm Springs. Flights are based on user searches made on Cheapflights and were last updated on October 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 4 airlines flying from Palm Springs to Chicago
Discover the top 4 airlines that operate flights from Palm Springs to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$245 | Average$310 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$251 | Average$418 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$266 | Average$462 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$269 | Average$403 | FlexibilityNo cancel fee | On-time69% |