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Cheap flights from Palm Springs to Chicago from $82

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Palm Springs to Chicago departing on 10/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Palm Springs to Chicago (PSP-MDW)

Cheap round-trip flights

Frontier Logo
12:00 pm - 12:24 amPSP-MDW
10h 24m1 stop
Frontier Logo
9:43 pm - 11:07 amMDW-PSP
15h 24m2 stops
$192Frontier
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Mon, Oct 27 - Thu, Oct 30
Southwest Logo
10:30 am - 8:25 pmPSP-MDW
7h 55m1 stop
Southwest Logo
2:40 pm - 6:35 pmMDW-PSP
5h 55m1 stop
$270Southwest
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Fri, Nov 7 - Sat, Nov 15
Southwest Logo
5:35 am - 4:20 pmPSP-MDW
8h 45m2 stops
Southwest Logo
2:40 pm - 6:35 pmMDW-PSP
5h 55m1 stop
$275Southwest
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Fri, Nov 7 - Sat, Nov 15
Delta Logo
4:59 pm - 9:40 amPSP-MDW
14h 41m2 stops
Delta Logo
2:00 pm - 9:34 pmMDW-PSP
9h 34m2 stops
$283Delta
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Fri, Nov 7 - Sat, Nov 15
Southwest Logo
11:00 am - 6:10 pmPSP-MDW
5h 10m1 stop
Southwest Logo
4:35 pm - 8:55 pmMDW-PSP
6h 20m1 stop
$287Southwest
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Wed, Sep 10 - Wed, Sep 17
Southwest Logo
3:20 pm - 12:05 amPSP-MDW
6h 45m1 stop
Southwest Logo
6:15 pm - 10:10 pmMDW-PSP
5h 55m1 stop
$306Southwest
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Fri, Sep 26 - Mon, Sep 29
Southwest Logo
5:30 am - 1:40 pmPSP-MDW
6h 10m1 stop
Southwest Logo
7:50 am - 4:35 pmMDW-PSP
10h 45m1 stop
$307Southwest
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Wed, Nov 5 - Sun, Nov 9
Southwest Logo
5:30 am - 4:30 pmPSP-MDW
9h 00m2 stops
Southwest Logo
4:35 pm - 8:55 pmMDW-PSP
6h 20m1 stop
$311Southwest
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Wed, Sep 10 - Wed, Sep 17
Delta Logo
12:20 pm - 8:40 amPSP-MDW
18h 20m2 stops
Delta Logo
1:08 pm - 9:20 pmMDW-PSP
10h 12m2 stops
$327Delta
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Wed, Sep 17 - Tue, Sep 23
Delta Logo
12:20 pm - 8:40 amPSP-MDW
18h 20m2 stops
Delta Logo
1:08 pm - 9:20 pmMDW-PSP
10h 12m2 stops
$415Delta
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Tue, Sep 16 - Tue, Sep 23

Southwest flights from Palm Springs to Chicago Midway Airport

Our best Southwest deals on Palm Springs to Chicago Midway Airport flight tickets
Southwest
Nov 7
PSP10:30 amPalm Springs
7h 55m
1 stop
MDW8:25 pmChicago Midway
Nov 15
MDW2:40 pmChicago Midway
5h 55m
1 stop
PSP6:35 pmPalm Springs
$270
Find similar
Southwest
Nov 7
PSP5:35 amPalm Springs
8h 45m
2 stops
MDW4:20 pmChicago Midway
Nov 15
MDW2:40 pmChicago Midway
5h 55m
1 stop
PSP6:35 pmPalm Springs
$275
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Southwest
Sep 10
PSP11:00 amPalm Springs
5h 10m
1 stop
MDW6:10 pmChicago Midway
Sep 17
MDW4:35 pmChicago Midway
6h 20m
1 stop
PSP8:55 pmPalm Springs
$287
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Delta flights from Palm Springs to Chicago Midway Airport

Our best Delta deals on Palm Springs to Chicago Midway Airport flight tickets
Delta
Nov 7
PSP4:59 pmPalm Springs
14h 41m
2 stops
MDW9:40 amChicago Midway
Nov 15
MDW2:00 pmChicago Midway
9h 34m
2 stops
PSP9:34 pmPalm Springs
$283
Find similar
Delta
Sep 17
PSP12:20 pmPalm Springs
18h 20m
2 stops
MDW8:40 amChicago Midway
Sep 23
MDW1:08 pmChicago Midway
10h 12m
2 stops
PSP9:20 pmPalm Springs
$327
Find similar
Delta
Sep 16
PSP12:20 pmPalm Springs
18h 20m
2 stops
MDW8:40 amChicago Midway
Sep 23
MDW1:08 pmChicago Midway
10h 12m
2 stops
PSP9:20 pmPalm Springs
$415
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momondo Fare Finder

 
Customize your flight search to find flights from Palm Springs to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated August 20, 2025.
Use the filters below to find and compare flights from Palm Springs to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Mon 10/27

12:00 pm-12:24 am

1 stop10h 24m

Chicago Midway

Thu 10/30

9:43 pm-11:07 am

2 stops15h 24m

$192

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 11/7

10:30 am-8:25 pm

1 stop7h 55m

Chicago Midway

Sat 11/15

2:40 pm-6:35 pm

1 stop5h 55m

$270

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 11/7

5:35 am-4:20 pm

2 stops8h 45m

Chicago Midway

Sat 11/15

2:40 pm-6:35 pm

1 stop5h 55m

$275

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 11/7

4:59 pm-9:40 am

2 stops14h 41m

Chicago Midway

Sat 11/15

2:00 pm-9:34 pm

2 stops9h 34m

$283

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 9/10

11:00 am-6:10 pm

1 stop5h 10m

Chicago Midway

Wed 9/17

4:35 pm-8:55 pm

1 stop6h 20m

$287

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 9/26

3:20 pm-12:05 am

1 stop6h 45m

Chicago Midway

Mon 9/29

6:15 pm-10:10 pm

1 stop5h 55m

$306

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 11/5

5:30 am-1:40 pm

1 stop6h 10m

Chicago Midway

Sun 11/9

7:50 am-4:35 pm

1 stop10h 45m

$307

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 9/10

5:30 am-4:30 pm

2 stops9h 00m

Chicago Midway

Wed 9/17

4:35 pm-8:55 pm

1 stop6h 20m

$311

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 9/17

12:20 pm-8:40 am

2 stops18h 20m

Chicago Midway

Tue 9/23

1:08 pm-9:20 pm

2 stops10h 12m

$327

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 9/16

12:20 pm-8:40 am

2 stops18h 20m

Chicago Midway

Tue 9/23

1:08 pm-9:20 pm

2 stops10h 12m

$415

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Palm Springs to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of July is, on average, the cheapest month to fly to Chicago Midway Airport from Palm Springs, with most prices found around $288. If you are unable to visit Chicago Midway Airport during the month of July, then departing from Palm Springs during the month February is also very affordable. Most momondo users find prices during this month for around $307.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Palm Springs. The lowest ticket price found for a Wednesday departure recently was $430. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Saturday is the most expensive day to depart from Palm Springs because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $768.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Palm Springs in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $408 when looking at flights departing in the afternoon. Try not to purchase tickets at noon because they tend to be around $552. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Palm Springs to Chicago Midway flight route?

Fly from Palm Springs to Chicago Midway for the best Palm Springs - Chicago Midway flight prices

What cabin class options are available on Palm Springs to Chicago Midway flights?

There are 1 cabin classes available to choose from on Palm Springs to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Palm Springs to Chicago Midway Airport flights?

You could potentially save up to 16% on your flight if you consider stops on a Palm Springs to Chicago Midway Airport flight.

When to book flights from Palm Springs to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Palm Springs to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Palm Springs to Chicago Midway Airport (PSP to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Palm Springs to Chicago Midway Airport

Fastest flight time

3h 40m

Direct flights

Mon, Tue, Wed, Thu, Sat and Sun
The fastest flight from Palm Springs to Chicago Midway Airport takes 3h 40m
Direct flights go from Palm Springs to Chicago Midway Airport on Monday, Tuesday, Wednesday, Thursday, Saturday and Sunday. The only airline offering direct flights is Southwest.
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  • How far is Palm Springs to Chicago Midway by plane?

    A flight from Palm Springs to Chicago Midway will travel around 1655.0 mi. Flights usually cover this in 3h 45m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Palm Springs Airport to Chicago Midway Airport?

    Prices for flights from Palm Springs Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Palm Springs Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Palm Springs Airport to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Palm Springs Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Palm Springs to Chicago Midway Airport?

  • What is the most popular airline from Palm Springs to Chicago Midway Airport?

Best airlines flying from Palm Springs to Chicago Midway Airport

Compare and see reviews for airlines that fly from Palm Springs to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $288Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Palm Springs to Chicago?

Finding the right flight to Chicago from Palm Springs is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Palm Springs to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from Palm Springs on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Palm Springs to Chicago?

Once you have performed a search for Palm Springs to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Palm Springs to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Palm Springs to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

An easier way to manage your Chicago Midway Airport trip

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