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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 8/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Palm Springs to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
11:05 am - 8:45 pm
PSP
-
MDW
7h 40m
1 stop
Southwest Logo
10:20 am - 4:50 pm
MDW
-
PSP
8h 30m
1 stop
$271Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
11:05 am - 8:45 pm
PSP
-
MDW
7h 40m
1 stop
Southwest Logo
3:50 pm - 9:55 pm
MDW
-
PSP
8h 05m
1 stop
$310Southwest
Wed, Aug 12 - Tue, Aug 18
Southwest Logo
11:05 am - 10:50 pm
PSP
-
MDW
9h 45m
2 stops
Southwest Logo
6:00 pm - 9:55 pm
MDW
-
PSP
5h 55m
1 stop
$315Southwest
Wed, Aug 12 - Tue, Aug 18
Southwest Logo
5:30 pm - 5:45 am
PSP
-
MDW
10h 15m
1 stop
Southwest Logo
9:55 am - 8:55 pm
MDW
-
PSP
13h 00m
2 stops
$326Southwest
Tue, Sep 15 - Sat, Sep 19
Southwest Logo
11:20 am - 10:15 pm
PSP
-
MDW
8h 55m
2 stops
Southwest Logo
6:55 am - 10:45 am
MDW
-
PSP
5h 50m
1 stop
$334Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
11:05 am - 8:45 pm
PSP
-
MDW
7h 40m
1 stop
Southwest Logo
6:55 am - 10:45 am
MDW
-
PSP
5h 50m
1 stop
$339Southwest
Tue, Aug 18 - Sat, Aug 22
Southwest Logo
11:05 am - 8:45 pm
PSP
-
MDW
7h 40m
1 stop
Southwest Logo
5:00 pm - 10:10 pm
MDW
-
PSP
7h 10m
2 stops
$340Southwest
Tue, Aug 11 - Fri, Aug 14
Southwest Logo
7:05 am - 4:00 pm
PSP
-
MDW
6h 55m
2 stops
Southwest Logo
4:40 pm - 9:55 pm
MDW
-
PSP
7h 15m
2 stops
$349Southwest
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
11:20 am - 10:15 pm
PSP
-
MDW
8h 55m
2 stops
Southwest Logo
6:55 am - 10:45 am
MDW
-
PSP
5h 50m
1 stop
$354Southwest
Sat, Aug 22 - Sat, Aug 29
Southwest Logo
11:05 am - 10:50 pm
PSP
-
MDW
9h 45m
2 stops
Southwest Logo
10:30 am - 4:50 pm
MDW
-
PSP
8h 20m
2 stops
$359Southwest
Wed, Aug 12 - Tue, Aug 18

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Southwest flights from Palm Springs to Chicago Midway Airport

Our best Southwest deals on Palm Springs to Chicago Midway Airport flight tickets
Southwest
Aug 26
PSP11:05 amPalm Springs
7h 40m
1 stop
MDW8:45 pmChicago Midway
Sep 1
MDW10:20 amChicago Midway
8h 30m
1 stop
PSP4:50 pmPalm Springs
$271
Southwest
Aug 12
PSP11:05 amPalm Springs
7h 40m
1 stop
MDW8:45 pmChicago Midway
Aug 18
MDW3:50 pmChicago Midway
8h 05m
1 stop
PSP9:55 pmPalm Springs
$310
Southwest
Aug 12
PSP11:05 amPalm Springs
9h 45m
2 stops
MDW10:50 pmChicago Midway
Aug 18
MDW6:00 pmChicago Midway
5h 55m
1 stop
PSP9:55 pmPalm Springs
$315

Delta flights from Palm Springs to Chicago Midway Airport

Our best Delta deals on Palm Springs to Chicago Midway Airport flight tickets
Delta
Jul 7
PSP5:15 pmPalm Springs
13h 58m
2 stops
MDW9:13 amChicago Midway
Jul 11
MDW9:19 amChicago Midway
9h 19m
2 stops
PSP4:38 pmPalm Springs
$377
Delta
Jul 31
PSP5:15 pmPalm Springs
13h 58m
2 stops
MDW9:13 amChicago Midway
Aug 7
MDW1:25 pmChicago Midway
10h 05m
2 stops
PSP9:30 pmPalm Springs
$409
Delta
Jul 31
PSP5:15 pmPalm Springs
13h 58m
2 stops
MDW9:13 amChicago Midway
Aug 4
MDW1:25 pmChicago Midway
10h 05m
2 stops
PSP9:30 pmPalm Springs
$434

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 July 3, 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

Wed 8/26

11:05 am-8:45 pm

1 stop7h 40m

Chicago Midway

Tue 9/1

10:20 am-4:50 pm

1 stop8h 30m

$271

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 8/12

11:05 am-8:45 pm

1 stop7h 40m

Chicago Midway

Tue 8/18

3:50 pm-9:55 pm

1 stop8h 05m

$310

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 8/12

11:05 am-10:50 pm

2 stops9h 45m

Chicago Midway

Tue 8/18

6:00 pm-9:55 pm

1 stop5h 55m

$315

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 9/15

5:30 pm-5:45 am

1 stop10h 15m

Chicago Midway

Sat 9/19

9:55 am-8:55 pm

2 stops13h 00m

$326

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 8/15

11:20 am-10:15 pm

2 stops8h 55m

Chicago Midway

Sat 8/22

6:55 am-10:45 am

1 stop5h 50m

$334
Quickest round-trip

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 8/18

11:05 am-8:45 pm

1 stop7h 40m

Chicago Midway

Sat 8/22

6:55 am-10:45 am

1 stop5h 50m

$339

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Tue 8/11

11:05 am-8:45 pm

1 stop7h 40m

Chicago Midway

Fri 8/14

5:00 pm-10:10 pm

2 stops7h 10m

$340

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 8/26

7:05 am-4:00 pm

2 stops6h 55m

Chicago Midway

Tue 9/1

4:40 pm-9:55 pm

2 stops7h 15m

$349

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Sat 8/22

11:20 am-10:15 pm

2 stops8h 55m

Chicago Midway

Sat 8/29

6:55 am-10:45 am

1 stop5h 50m

$354

Palm SpringsChicago

PSP - MDW

PSPMDW

Palm Springs

Wed 8/12

11:05 am-10:50 pm

2 stops9h 45m

Chicago Midway

Tue 8/18

10:30 am-4:50 pm

2 stops8h 20m

$359

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 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

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

There is only 1 cabin class available to choose from on Palm Springs to Chicago Midway Airport 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?

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
7.9
4,250 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
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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