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Cheap flights from Palm Springs to Chicago from $136

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 5/27. 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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0 bags

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Find the cheapest flights from Palm Springs to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:10 pm - 9:14 am
PSP
-
MDW
14h 04m
2 stops
Delta Logo
6:00 am - 11:23 am
MDW
-
PSP
7h 23m
1 stop
$276Delta
Tue, Jun 16 - Tue, Nov 3
Southwest Logo
3:05 pm - 11:40 pm
PSP
-
MDW
6h 35m
1 stop
Southwest Logo
6:30 am - 10:15 am
MDW
-
PSP
5h 45m
1 stop
$309Southwest
Fri, May 29 - Tue, Jun 2
Southwest Logo
3:05 pm - 11:40 pm
PSP
-
MDW
6h 35m
1 stop
Southwest Logo
4:00 pm - 9:50 pm
MDW
-
PSP
7h 50m
2 stops
$314Southwest
Fri, May 29 - Tue, Jun 2
Delta Logo
5:10 pm - 9:14 am
PSP
-
MDW
14h 04m
2 stops
Delta Logo
6:00 am - 11:23 am
MDW
-
PSP
7h 23m
1 stop
$315Delta
Tue, Jun 16 - Sun, Nov 1
Delta Logo
5:10 pm - 9:14 am
PSP
-
MDW
14h 04m
2 stops
Delta Logo
9:19 am - 4:38 pm
MDW
-
PSP
9h 19m
2 stops
$320Delta
Fri, Jul 3 - Sat, Jul 11
Southwest Logo
6:25 pm - 5:45 am
PSP
-
MDW
9h 20m
1 stop
Southwest Logo
2:40 pm - 7:00 pm
MDW
-
PSP
6h 20m
1 stop
$342Southwest
Wed, May 27 - Sat, May 30
Southwest Logo
3:05 pm - 11:40 pm
PSP
-
MDW
6h 35m
1 stop
Southwest Logo
5:15 pm - 10:15 pm
MDW
-
PSP
7h 00m
1 stop
$345Southwest
Fri, May 29 - Mon, Jun 1
Southwest Logo
4:10 pm - 1:25 am
PSP
-
MDW
7h 15m
1 stop
Southwest Logo
5:10 am - 10:00 am
MDW
-
PSP
6h 50m
1 stop
$348Southwest
Fri, Jul 3 - Sat, Jul 11
Southwest Logo
11:20 am - 7:30 pm
PSP
-
MDW
6h 10m
1 stop
Southwest Logo
6:55 am - 10:45 am
MDW
-
PSP
5h 50m
1 stop
$349Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
11:05 am - 10:50 pm
PSP
-
MDW
9h 45m
2 stops
Southwest Logo
11:10 am - 3:15 pm
MDW
-
PSP
6h 05m
1 stop
$353Southwest
Wed, Sep 23 - Mon, Sep 28

Southwest flights from Palm Springs to Chicago Midway Airport

Our best Southwest deals on Palm Springs to Chicago Midway Airport flight tickets
Southwest
May 29
PSP3:05 pmPalm Springs
6h 35m
1 stop
MDW11:40 pmChicago Midway
Jun 2
MDW6:30 amChicago Midway
5h 45m
1 stop
PSP10:15 amPalm Springs
$309
Southwest
May 29
PSP3:05 pmPalm Springs
6h 35m
1 stop
MDW11:40 pmChicago Midway
Jun 2
MDW4:00 pmChicago Midway
7h 50m
2 stops
PSP9:50 pmPalm Springs
$314
Southwest
May 27
PSP6:25 pmPalm Springs
9h 20m
1 stop
MDW5:45 amChicago Midway
May 30
MDW2:40 pmChicago Midway
6h 20m
1 stop
PSP7:00 pmPalm Springs
$342

Delta flights from Palm Springs to Chicago Midway Airport

Our best Delta deals on Palm Springs to Chicago Midway Airport flight tickets
Delta
Jun 16
PSP5:10 pmPalm Springs
14h 04m
2 stops
MDW9:14 amChicago Midway
Nov 3
MDW6:00 amChicago Midway
7h 23m
1 stop
PSP11:23 amPalm Springs
$276
Delta
Jun 16
PSP5:10 pmPalm Springs
14h 04m
2 stops
MDW9:14 amChicago Midway
Nov 1
MDW6:00 amChicago Midway
7h 23m
1 stop
PSP11:23 amPalm Springs
$315
Delta
Jul 3
PSP5:10 pmPalm Springs
14h 04m
2 stops
MDW9:14 amChicago Midway
Jul 11
MDW9:19 amChicago Midway
9h 19m
2 stops
PSP4:38 pmPalm Springs
$320

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 May 17, 2026.
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

Cheapest round-trip

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 6/16

5:10 pm-9:14 am

2 stops14h 04m

Chicago Midway

Tue 11/3

6:00 am-11:23 am

1 stop7h 23m

$276

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 5/29

3:05 pm-11:40 pm

1 stop6h 35m

Chicago Midway

Tue 6/2

6:30 am-10:15 am

1 stop5h 45m

$309

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 5/29

3:05 pm-11:40 pm

1 stop6h 35m

Chicago Midway

Tue 6/2

4:00 pm-9:50 pm

2 stops7h 50m

$314

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 6/16

5:10 pm-9:14 am

2 stops14h 04m

Chicago Midway

Sun 11/1

6:00 am-11:23 am

1 stop7h 23m

$315

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 7/3

5:10 pm-9:14 am

2 stops14h 04m

Chicago Midway

Sat 7/11

9:19 am-4:38 pm

2 stops9h 19m

$320

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 5/27

6:25 pm-5:45 am

1 stop9h 20m

Chicago Midway

Sat 5/30

2:40 pm-7:00 pm

1 stop6h 20m

$342

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 5/29

3:05 pm-11:40 pm

1 stop6h 35m

Chicago Midway

Mon 6/1

5:15 pm-10:15 pm

1 stop7h 00m

$345

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Fri 7/3

4:10 pm-1:25 am

1 stop7h 15m

Chicago Midway

Sat 7/11

5:10 am-10:00 am

1 stop6h 50m

$348
Quickest round-trip

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 8/22

11:20 am-7:30 pm

1 stop6h 10m

Chicago Midway

Sat 8/29

6:55 am-10:45 am

1 stop5h 50m

$349

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 9/23

11:05 am-10:50 pm

2 stops9h 45m

Chicago Midway

Mon 9/28

11:10 am-3:15 pm

1 stop6h 05m

$353

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 typical price of a round-trip flight between Palm Springs and Chicago Midway Airport?

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

The month of April is, on average, the cheapest month to fly to Chicago Midway Airport from Palm Springs, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of April, then departing from Palm Springs during the month March is also very affordable. Most momondo users find prices during this month for around $0.

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 morning is the least expensive time of day to depart. momondo users have found prices as low as $464 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $485. 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

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

No. A direct flight is the cheapest option for a flight between Palm Springs to Chicago Midway Airport.

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

5h 15m

Direct flights

None
The fastest flight from Palm Springs to Chicago Midway Airport takes 5h 15m
There are no direct flights from Palm Springs to Chicago Midway Airport. There are no popular flight routes from Palm Springs to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Palm Springs to Chicago Midway Airport

  • 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 5h 15m, 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 $273Free CancellationRating
8.0
4,291 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
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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