PBI - MDW

$135 Find Cheap Flights from West Palm Beach 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 West Palm Beach to Midway departing on 12/30. 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 West Palm Beach 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 West Palm Beach to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$230
Multiple Airlines
Fri 1/30Mon 2/2
PBI - MDW • 1 stop
Cheapest one-way
$135
Frontier
Tue 12/30
PBI - MDW • 1 stop
Top airlines
Frontier
Cheapest • from $231 (round-trip)
Southwest
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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We hope you love your trip to Midway!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from West Palm Beach to Midway (PBI-MDW)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from West Palm Beach 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 West Palm Beach to Midway

Fri, Jan 30 - Mon, Feb 2
Multiple Airlines Logo
3:34 pm - 10:19 pm
PBI
-
MDW
7h 45m1 stop
Multiple Airlines Logo
1:00 pm - 12:57 pm
MDW
-
PBI
22h 57m2 stops
$230Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Frontier Logo
1:27 pm - 7:47 pm
PBI
-
MDW
7h 20m1 stop
Frontier Logo
7:53 pm - 3:34 pm
MDW
-
PBI
18h 41m2 stops
$231Frontier
Sat, Jan 17 - Thu, Jan 22
Delta Logo
12:45 pm - 4:29 pm
PBI
-
MDW
4h 44m1 stop
Delta Logo
6:00 am - 11:49 am
MDW
-
PBI
4h 49m1 stop
$233Delta
Mon, Jan 12 - Thu, Jan 22
Frontier Logo
8:23 pm - 10:34 am
PBI
-
MDW
15h 11m2 stops
Frontier Logo
5:01 pm - 2:34 pm
MDW
-
PBI
20h 33m1 stop
$235Frontier
Sun, Feb 22 - Fri, Feb 27
Frontier Logo
1:36 pm - 7:59 pm
PBI
-
MDW
7h 23m1 stop
Frontier Logo
7:53 pm - 3:34 pm
MDW
-
PBI
18h 41m2 stops
$239Frontier
Sat, Jan 10 - Sun, Jan 11
Multiple Airlines Logo
11:55 am - 10:27 pm
PBI
-
MDW
11h 32m2 stops
Multiple Airlines Logo
6:10 am - 5:02 pm
MDW
-
PBI
9h 52m1 stop
$244Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
Multiple Airlines Logo
9:23 am - 10:29 pm
PBI
-
MDW
14h 06m2 stops
Multiple Airlines Logo
6:00 am - 12:32 pm
MDW
-
PBI
5h 32m1 stop
$248Multiple Airlines
Wed, Feb 25 - Sat, Feb 28
Southwest Logo
11:25 am - 6:05 pm
PBI
-
MDW
7h 40m1 stop
Southwest Logo
5:40 am - 11:25 am
MDW
-
PBI
4h 45m1 stop
$249Southwest
Fri, Feb 20 - Sun, Feb 22
Frontier Logo
1:16 pm - 10:34 pm
PBI
-
MDW
10h 18m1 stop
Frontier Logo
6:00 am - 12:32 pm
MDW
-
PBI
5h 32m1 stop
$253Frontier
Tue, Jan 6 - Wed, Jan 7
Southwest Logo
7:05 am - 1:10 pm
PBI
-
MDW
7h 05m2 stops
Southwest Logo
1:15 pm - 8:45 pm
MDW
-
PBI
6h 30m1 stop
$254Southwest
Booking Insights

KAYAK's insights & trends for West Palm Beach to Midway flights

Get data-powered insights and trends into flights from West Palm Beach 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 West Palm Beach to Chicago Midway Airport?

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

When flying from West Palm Beach to Chicago Midway Airport, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to West Palm Beach, you’ll find the best rates on Saturdays and the most expensive ones on Fridays.

Good to know

Low seasonOctober
Cheapest flight$135
Best time to beat the crowds with an average 39% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from West Palm Beach to Chicago Midway Airport

When to book flights from West Palm Beach to Midway

Are your dates flexible? Find out the best times to travel from West Palm Beach 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 West Palm Beach to Chicago Midway Airport flights

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

    In the last 3 days, the lowest price for a flight from West Palm Beach to Chicago Midway Airport was $135 for a one-way ticket and $231 for a round-trip.

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

    A passport is not required to fly from West Palm Beach to Chicago Midway Airport.

  • Which airports will I be using when flying from West Palm Beach to Chicago Midway Airport?

    On your way to Chicago Midway Airport, you’ll fly out from Palm Beach Intl. You’ll be landing at Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from West Palm Beach to Chicago Midway Airport?

    SkyTeam is the only airline alliance operating flights between West Palm Beach and Chicago Midway Airport.

  • Which is the best airline for flights from West Palm Beach to Chicago, Delta or Southwest?

    The two airlines most popular with KAYAK users for flights from West Palm Beach to Chicago are Delta and Southwest. With an average price for the route of $302 and an overall rating of 7.9, Delta is the most popular choice. Southwest is also a great choice for the route, with an average price of $448 and an overall rating of 7.9.

  • How does KAYAK find such low prices on flights from West Palm Beach 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 West Palm Beach to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from West Palm Beach 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 West Palm Beach 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 West Palm Beach 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 West Palm Beach with another airline. Booking your flights between West Palm Beach 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 West Palm Beach 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 West Palm Beach up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from West Palm Beach to Midway

 
See real verified KAYAK customer reviews for airlines flying from West Palm Beach 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 West Palm Beach 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.
7.9
SouthwestOverall score based on 4250 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

2.0 MediocreCharity, Nov 2025
MSP - MDW
Read more Southwest reviews

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

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

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

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.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Cramped seating for me. Luckily it wasn’t a long flight

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Everything you need to know for your flight from West Palm Beach to Midway

Information on your arrival and departure airports