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Flights from Palm Springs to Chicago – Direct & connecting routes

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PSP to MDW flights and routes map PSP to MDW – All flight route options from Palm Springs International, California, USA to Chicago Midway International, Illinois, USA. These flights are operated by Southwest Airlines. You can either fly non-stop to Chicago or with one stop via Denver. The shortest flight time is 3 hours and 45 minutes. See the full flight schedule and time table, including departure times, airlines and stopover details to find the best option for you.

From
To
USA PSP Palm Springs Palm Springs, CA, USA
USA MDW Chicago Midway , IL, USA
PSP
Palm Springs
USAPalm Springs, CA, USA
Chicago Midway
USAChicago, IL, USA
MDW
1 direct route found »
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2 routes with 1 stop found »
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Non-stop route options:

Duration

Southwest Airlines
Non-stop with Southwest Airlines. 0-1 flights per day.
Begins in 22/11

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3h 45m

Begins in 22/11
Southwest Airlines
Non-stop with Southwest Airlines.
3h 45m
0-1 flights per day.
Begins in 22/11
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1 stop route options with the same airline:

Duration

Via Denver DEN
1 stop with Southwest Airlines. 0-4 flights per day.

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6h 20m

Via Denver DEN
1 stop with Southwest Airlines.
6h 20m
0-4 flights per day.
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Via Las Vegas LAS
1 stop with Southwest Airlines. 0-2 flights per day.

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6h 53m

Via Las Vegas LAS
1 stop with Southwest Airlines.
6h 53m
0-2 flights per day.
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Palm Springs to Chicago flights

With over 23 flights every week and 3 different airlines you have a wide range of options. You can fly non-stop to Chicago (MDW) from Palm Springs (PSP) with Southwest Airlines or choose a connecting flight via Denver (DEN) or Las Vegas (LAS) if it suits you better.

Palm Springs to Chicago with Southwest Airlines

You can fly non-stop every weekday except Mondays with departure times at 11:05, 11:45 or 13:00. You can also take a connecting flight via Denver or Las Vegas.

Note Non-stop flights with Southwest Airlines will begin in Nov 2025.

Distance & flight times: Palm Springs International to Midway International Airport

The shortest flight time between PSP and MDW is 3 hours and 45 minutes.

ViaTotal flight timeLayover timeDistance
Direct3h 45m-1663 miles (2676 km)
DEN Denver6h 20m2h 35m1677 miles (2698 km)
LAS Las Vegas6h 53m3h 0m1699 miles (2734 km)
The flight times and layover times in the table above are approximate and may vary depending on flight number, aircraft, airline, weather, and time of day.PSP-MDW flight routesPalm Springs to Chicago flight routes illustrated on a map.
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Palm Springs - Chicago route map and flight paths
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Show all destinations from PSP Show all destinations from MDW

You can fly non-stop from Palm Springs (PSP) to Chicago (MDW) with Southwest Airlines. The flight takes approximately 3 hours and 45 minutes. If you travel with a connecting flight instead, for example via Denver, the total flight time will be 6 hours and 20 minutes.

If you're interested in direct flights, Southwest Airlines is available. For flights with stopovers, Southwest Airlines is also an option.

The flight time between Palm Springs (PSP) and Chicago Midway International (MDW) is approximately 3 hours and 45 minutes. The distance between the two airports is 1699 miles (or 2734 kilometers).

Yes, you can fly non-stop to MDW from PSP with Southwest Airlines.

A codeshare agreement means that cooperating airlines are able to sell seats on each other’s flights. This means that you are able to travel to more destinations than your airline of choice normally offers. Codeshare flights are also beneficial because of the seamless transits you can get with connecting flights from the same airline. The downside of choosing a codeshare flight can be that you in some cases can’t upgrade codeshare flights or use elite benefits.

A connecting or transit flight means that you reach your final destination through two or more flights – in other words a non-direct flight. You will change to a new aircraft after your first flight, this may include moving to another terminal at the airport aswell. The time required to transfer passengers and luggage between flights is called Minimum Connecting Time (MCT) and are always taken into account here on Flightroutes.com.

If you bought your whole flight on a single ticket, the airline will book you on the next available connecting flight.

With connecting flights, checked in luggage is most commonly forwarded to your final destination when buying a single ticket for both flights.

If you miss your connecting flight due to circumstances outside your control such as your first flight being delayed, you should turn to your airline who will provide you with a seat on the next available flight. This is usually done free of charge, and only applies if you purchased your trip as one ticket. If the next connecting flight is the following day, the airline usually provides accommodation and meals.
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