Title: CA $333 Cheap Flights from Palm Springs (PSP) to Chicago (MDW) - Expedia.ca ![City of Chicago. Image of Chicago downtown and Chicago River with bridges at sunny summer day](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/178248/e6aa83ce-7ad8-43a5-9d1d-b055eefa7e78.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # CA $333 Cheap Flights from Palm Springs (PSP) to Chicago (MDW) [View CA $333 flight on Fri, Jan 30, 2026](https://expedia.ca/Flights-Search?trip=oneway&leg1=from:PSP,to:MDW,departure:30/01/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:333.00&airProductToken=AQpuCjQIxJgBEgMzNDkYz3wg4Fwoie2DAzD_7oMDOEVAAFgBaglNQUlOQkFTSUNyCFVBN05BMEJDCjYIxJgBEgQxMDc2GOBcIOywASi374MDMKbwgwM4RUABWAFqCU1BSU5CQVNJQ3IIVUE3TkEwQkMSCggBEAEYASoCREwYASIECAEQASgCKAMoBDAB) - [Roundtrip](?flightType=roundtrip) - [One-way](?flightType=oneway) - [Multi-city](?flightType=multicity) ### Travellers Adults ChildrenAges 2 to 17 InfantsYounger than 2 EconomyPremium economyBusiness classFirst class Leaving from Going to Departing Returning Add a place to stay Add a car Direct flights only ## Popular airlines from Palm Springs Intl. Airport (PSP) to Chicago Midway Airport (MDW) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_WN.svg) Southwest Airlines [](https://www.expedia.ca/Flights-Search?leg1=from:PSP,to:MDW,departure:05/02/2026TANYT&leg2=from:MDW,to:PSP,departure:12/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}]) - ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/09/23/landing_airline_sq_logo_DL.svg) Delta [](https://www.expedia.ca/Flights-Search?leg1=from:PSP,to:MDW,departure:05/02/2026TANYT&leg2=from:MDW,to:PSP,departure:12/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}]) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__notification.svg) ### Be in the know Get alerts if flight prices drop or rise\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Book smarter Save up to 30% on select hotels after you book a flight\* - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Earn twice Earn your airline miles on top of our rewards [Sign in](https://www.expedia.ca/login) ## Cheap flights from Palm Springs (PSP) to Chicago (MDW) Prices were available within the past 7 days and start at CA $333 for one-way flights and CA $450 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply. All deals One way Roundtrip ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 5 - Mon, Feb 16 PSP Palm Springs MDW Chicago CA $450 Roundtrip found 7 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSP,to:MDW,departure:05/02/2026TANYT&leg2=from:MDW,to:PSP,departure:16/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:449.50&airProductToken=AQpECh8IxJgBEgMzNDkYz3wg4FwoybCEAzC_soQDOEVAAFgBCiEIxJgBEgQxMDc2GOBcIOywASj3soQDMOazhAM4RUABWAEKRAohCMSYARIEMzc3OBjssAEgzHwo1qmFAzC8qoUDOEVAAFgBCh8IxJgBEgM3NDgYzHwgz3wo_KqFAzDkrIUDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 5 - Mon, Feb 9 PSP Palm Springs MDW Chicago CA $498 Roundtrip found 7 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSP,to:MDW,departure:05/02/2026TANYT&leg2=from:MDW,to:PSP,departure:09/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:497.90&airProductToken=AQpECh8IxJgBEgMzNDkYz3wg4FwoybCEAzC_soQDOEVAAFgBCiEIxJgBEgQxMDc2GOBcIOywASj3soQDMOazhAM4RUABWAEKRAohCMSYARIEMzc3OBjssAEgzHwo-dqEAzDh24QDOEVAAFgBCh8IxJgBEgM3NDgYzHwgz3wom9yEAzCF3oQDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Thu, Feb 5 - Wed, Feb 11 PSP Palm Springs MDW Chicago CA $589 Roundtrip found 7 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSP,to:MDW,departure:05/02/2026TANYT&leg2=from:MDW,to:PSP,departure:11/02/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:588.20&airProductToken=AQpECh8IxJgBEgMzNDkYz3wg4FwoybCEAzC_soQDOEVAAFgBCiEIxJgBEgQxMDc2GOBcIOywASj3soQDMOazhAM4RUABWAEKRAohCMSYARIEMTI4NRjssAEg4Fwo0O-EAzDN8IQDOEVAAFgBCh8IxJgBEgMzNDkY4Fwgz3wopPGEAzDD84QDOEVAAVgBEgoIARABGAEqAkRMGAEiBAgBEAEoBDAB) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Mar 27 - Fri, Apr 3 PSP Palm Springs MDW Chicago CA $1,616 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSP,to:MDW,departure:27/03/2026TANYT&leg2=from:MDW,to:PSP,departure:03/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1615.90&airProductToken=AQpuCjQIxJgBEgMzNDkYz3wg4Fwoo-KIAzCP5IgDOEJAAFgBaglNQUlOQ0xBU0NyCEJBVk9BME1DCjYIxJgBEgQxMDc2GOBcIOywASj_5IgDMPPliAM4QkABWAFqCU1BSU5DTEFTQ3IIQkFWT0EwTUMKbgo2CMSYARIEMTI4NRjssAEg4Fwo9KyJAzDsrYkDOEtAAFgBaglNQUlOQ0xBU0NyCEtBVU9BME1FCjQIxJgBEgMzNDkY4Fwgz3wonq6JAzC8sIkDOEtAAVgBaglNQUlOQ0xBU0NyCEtBVU9BME1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ![Delta](//images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/DL.gif) Fri, Mar 27 - Fri, Apr 3 PSP Palm Springs MDW Chicago CA $1,852 Roundtrip found 5 hours ago [](https://expedia.ca/Flights-Search?trip=roundtrip&leg1=from:PSP,to:MDW,departure:27/03/2026TANYT&leg2=from:MDW,to:PSP,departure:03/04/2026TANYT&passengers=children:0,adults:1,seniors:0,infantinlap:N&mode=search&options=sortby:price&paandi=true&flp=mdl:flights-flex-module,price:1851.30&airProductToken=AQpuCjQIxJgBEgMzNDkYz3wg4Fwoo-KIAzCP5IgDOEJAAFgBaglNQUlORVhUUkFyCEJBVlpBME1FCjYIxJgBEgQxMDc2GOBcIOywASj_5IgDMPPliAM4QkABWAFqCU1BSU5FWFRSQXIIQkFWWkEwTUUKbgo2CMSYARIEMTI4NRjssAEg4Fwo9KyJAzDsrYkDOEtAAFgBaglNQUlORVhUUkFyCEtBVVpBME1FCjQIxJgBEgMzNDkY4Fwgz3wonq6JAzC8sIkDOEtAAVgBaglNQUlORVhUUkFyCEtBVVpBME1FEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ) ## Find the cheapest month to fly from Palm Springs (PSP) to Chicago (MDW) ### February is typically the cheapest month to fly From CA $189 - CA $886 per traveller. ## Alternative airports near Chicago Prices were available within the past 7 days. Prices and availability are subject to change. [](https://www.expedia.ca/Flights-Search?leg1=from:PSP,to:ORD,departure:05/02/2026TANYT&leg2=from:ORD,to:PSP,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) ORD O'Hare Intl. 23 min [Flights from CA $596 ](https://www.expedia.ca/Flights-Search?leg1=from:PSP,to:ORD,departure:05/02/2026TANYT&leg2=from:ORD,to:PSP,departure:13/02/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE) __Flight from Palm Springs to Chicago (PSP - MDW) route information__ | Origin airport | Palm Springs Intl. | | ------------------- | ------------------ | | Destination airport | Midway Intl. | | Roundtrip price | CA $450 | | Distance | 2647 km | ## Palm Springs to Chicago Flights **The easy way to book your flights from Palm Springs to Chicago** With Expedia, it’s simple to find and book flights to Chicago from Palm Springs whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 airlines that cover this route. There are nonstop flights to Midway Intl., too. Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Palm Springs to Chicago today, tomorrow, or this week. **Save dollars with cheap flights from Palm Springs Intl., PSP to Midway Intl., MDW** Sort your search results by price to find great deals on your flight from Palm Springs to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Palm Springs currently is just CA $450 rising to CA $1,852\. Here are more money-saving tips: - Fly in February when flight prices are normally at their lowest - Book about a month to 6 weeks before you travel for the best prices to Chicago - Avoid peak season and weekends when flights can cost more - Early morning and late-night flights are sometimes cheaper, so try varying your travel times - One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free! **Reasons to choose Expedia for your flight to Chicago from Palm Springs** Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today. ## Frequently asked questions ### How much is a flight from Palm Springs Airport to MDW? ### Do I need to pay a cancellation fee if I cancel my flight from Palm Springs Intl. Airport (PSP) to MDW? ### How do I find cheap flights from Palm Springs Intl. Airport (PSP) to MDW that have flexible change policies? ### How many hours is the flight from Palm Springs Intl. Airport (PSP) to Midway Intl. Airport (MDW)? ### How far is the flight from Palm Springs Intl. Airport (PSP) to Midway Airport? ### Which airlines fly direct from PSP to Midway Intl. Airport (MDW)? ### Are Palm Springs Airport to Midway Intl. Airport (MDW) flight tickets cheaper when they're purchased at the last minute? \*Available to Expedia members.