PSP - MDW

$131 Find Cheap Flights from Palm Springs to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Palm Springs to Midway departing on 2/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Palm Springs to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$313
Overall average: $489
Southwest
Thu 11/27Wed 12/3
PSP - MDW • 1 stop
Cheapest non-stop
$374
Southwest
Wed 11/26Sun 11/30
PSP - MDW • Non-stop
Top airlines
Southwest
Cheapest • from $313 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
July
Cheapest • 31% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Nonstop flights
6 days a week
There are direct flights from Palm Springs to Midway 6 days a week: Mon, Tue, Wed, Fri, Sat, Sun.
Direct flights
Direct flights
Direct flights
Direct flights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Palm Springs to Midway (PSP-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Palm Springs to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Palm Springs to Midway

Thu, Nov 27 - Wed, Dec 3
Southwest Logo
7:20 am - 2:40 pmPSP-MDW
5h 20m1 stop
Southwest Logo
12:20 pm - 4:45 pmMDW-PSP
6h 25m1 stop
$313Southwest
Find Deal
Thu, Nov 27 - Wed, Dec 3
Delta Logo
12:33 pm - 11:40 pmPSP-MDW
9h 07m1 stop
Delta Logo
9:59 am - 4:16 pmMDW-PSP
8h 17m2 stops
$318Delta
Find Deal
Mon, Nov 24 - Thu, Nov 27
Delta Logo
12:33 pm - 11:40 pmPSP-MDW
9h 07m1 stop
Delta Logo
6:00 am - 11:23 amMDW-PSP
7h 23m1 stop
$330Delta
Find Deal
Wed, Nov 26 - Wed, Dec 3
Southwest Logo
1:00 pm - 6:45 pmPSP-MDW
3h 45mnonstop
Southwest Logo
9:45 am - 2:05 pmMDW-PSP
6h 20m1 stop
$342Southwest
Find Deal
Wed, Dec 3 - Tue, Dec 9
Delta Logo
12:37 pm - 11:47 pmPSP-MDW
9h 10m1 stop
Delta Logo
6:00 am - 11:27 amMDW-PSP
7h 27m1 stop
$345Delta
Find Deal
Wed, Nov 26 - Wed, Dec 3
Southwest Logo
1:00 pm - 6:45 pmPSP-MDW
3h 45mnonstop
Southwest Logo
1:20 pm - 9:00 pmMDW-PSP
9h 40m2 stops
$347Southwest
Find Deal
Tue, Dec 9 - Mon, Dec 15
Delta Logo
6:00 am - 6:00 pmPSP-MDW
10h 00m2 stops
Delta Logo
6:00 am - 11:27 amMDW-PSP
7h 27m1 stop
$350Delta
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
5:30 am - 1:40 pmPSP-MDW
6h 10m1 stop
Southwest Logo
9:45 am - 2:05 pmMDW-PSP
6h 20m1 stop
$352Southwest
Find Deal
Mon, Nov 24 - Wed, Dec 3
Southwest Logo
4:25 pm - 12:05 amPSP-MDW
5h 40m1 stop
Southwest Logo
8:25 am - 2:05 pmMDW-PSP
7h 40m1 stop
$353Southwest
Find Deal
Wed, Dec 3 - Mon, Dec 8
Delta Logo
6:00 am - 6:18 pmPSP-MDW
10h 18m2 stops
Delta Logo
1:14 pm - 9:50 pmMDW-PSP
10h 36m2 stops
$355Delta
Find Deal
Booking Insights

KAYAK's insights & trends for Palm Springs to Midway flights

Get data-powered insights and trends into flights from Palm Springs to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Palm Springs to Chicago Midway Airport?

The average price of all round-trip flights from Palm Springs to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago Midway Airport on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Saturday is the most expensive day to fly from Palm Springs to Chicago Midway Airport. For your return ticket, we recommend flying on a Friday and avoiding Tuesdays for the best deals.

What is the cheapest month to fly from Palm Springs to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Palm Springs to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Palm Springs to Chicago Midway Airport is July, where tickets cost $288 (return) on average. On the other hand, the most expensive months are October and November, where the average cost of round-trip tickets is $754 and $489 respectively.

Good to know

Low seasonSeptember
Cheapest flight$131
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 31% lower on average.
Flight from Palm Springs to Chicago Midway Airport

When to book flights from Palm Springs to Midway

Are your dates flexible? Find out the best times to travel from Palm Springs to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Palm Springs to Chicago Midway Airport flights

  • How many flights are there between Palm Springs and Chicago Midway Airport per day?

    There is a maximum of 1 nonstop flight a day that takes off from Palm Springs and lands in Chicago Midway Airport, with an average flight time of 3h 43m. The most common departure time is 11:00 am and most flights take off in the afternoon. Each week, there are 5 flights.

  • What is the cheapest flight from Palm Springs to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Palm Springs to Chicago Midway Airport was $131 for a one-way ticket and $313 for a round-trip.

  • Do I need a passport to fly between Palm Springs and Chicago Midway Airport?

    No

  • Which airlines offer Wi-Fi service onboard planes from Palm Springs to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Palm Springs to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Palm Springs to Chicago Midway Airport?

    The Airbus A320-100/200 is the aircraft model that flies most regularly on the Palm Springs to Chicago Midway Airport flight route.

  • On which days can I fly direct from Palm Springs to Chicago Midway Airport?

    You can catch a nonstop flight from Palm Springs to Chicago Midway Airport on Monday, Tuesday, Wednesday, Saturday, and Sunday.

  • How does KAYAK find such low prices on flights from Palm Springs to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Palm Springs to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Palm Springs to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Palm Springs is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Palm Springs to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Palm Springs with another airline. Booking your flights between Palm Springs and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Palm Springs to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Palm Springs up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Palm Springs to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $393 or less one-way.

Prefer to fly direct from Palm Springs to Chicago Midway Airport?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Palm Springs to Chicago Midway.
Find which airlines fly direct from Palm Springs Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Palm Springs to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Direct returns

Chicago Midway to Palm Springs

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Southwest

Southwest

See more direct flights

Reviews of the top airline flying from Palm Springs to Midway

 
See real verified KAYAK customer reviews for airlines flying from Palm Springs to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Palm Springs to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4243 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Everything you need to know for your flight from Palm Springs to Midway

Information on your arrival and departure airports

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