$104 Cheap Flights from West Palm Beach (PBI) to Chicago (MDW)

View $104 flight on Thu, Nov 6, 2025Opens in a new window

Popular airlines from Palm Beach Intl. Airport (PBI) to Chicago Midway Airport (MDW)

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

Prices were available within the past 7 days and start at $104 for one-way flights and $203 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Fri, Jul 25 - Tue, Jul 29
PBI
West Palm Beach
MDW
Chicago
$203 Roundtrip, found 1 day ago
$203
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Jul 25 from West Palm Beach to Chicago, returning Tue, Jul 29, priced at $203 found 1 day ago
Frontier Airlines
Fri, Jul 25 - Mon, Jul 28
PBI
West Palm Beach
MDW
Chicago
$206 Roundtrip, found 4 days ago
$206
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Jul 25 from West Palm Beach to Chicago, returning Mon, Jul 28, priced at $206 found 4 days ago
Southwest Airlines
Fri, Aug 15 - Mon, Aug 25
PBI
West Palm Beach
MDW
Chicago
$206 Roundtrip, found 6 days ago
$206
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Fri, Aug 15 from West Palm Beach to Chicago, returning Mon, Aug 25, priced at $206 found 6 days ago
Southwest Airlines
Thu, Aug 21 - Mon, Aug 25
PBI
West Palm Beach
MDW
Chicago
$207 Roundtrip, found 6 days ago
$207
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Aug 21 from West Palm Beach to Chicago, returning Mon, Aug 25, priced at $207 found 6 days ago
Delta
Fri, Aug 15 - Mon, Aug 25
PBI
West Palm Beach
MDW
Chicago
$211 Roundtrip, found 6 days ago
$211
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Aug 15 from West Palm Beach to Chicago, returning Mon, Aug 25, priced at $211 found 6 days ago
Southwest Airlines
Thu, Oct 9 - Mon, Oct 13
PBI
West Palm Beach
MDW
Chicago
$212 Roundtrip, found 8 hours ago
$212
Roundtrip
found 8 hours ago
Select Southwest Airlines flight, departing Thu, Oct 9 from West Palm Beach to Chicago, returning Mon, Oct 13, priced at $212 found 8 hours ago
Delta
Tue, Aug 12 - Tue, Aug 19
PBI
West Palm Beach
MDW
Chicago
$217 Roundtrip, found 10 hours ago
$217
Roundtrip
found 10 hours ago
Select Delta flight, departing Tue, Aug 12 from West Palm Beach to Chicago, returning Tue, Aug 19, priced at $217 found 10 hours ago
Southwest Airlines
Thu, Sep 4 - Mon, Sep 8
PBI
West Palm Beach
MDW
Chicago
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Thu, Sep 4 from West Palm Beach to Chicago, returning Mon, Sep 8, priced at $217 found 1 day ago
Southwest Airlines
Tue, Aug 26 - Thu, Sep 4
PBI
West Palm Beach
MDW
Chicago
$218 Roundtrip, found 10 hours ago
$218
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Tue, Aug 26 from West Palm Beach to Chicago, returning Thu, Sep 4, priced at $218 found 10 hours ago
Frontier Airlines
Mon, Aug 4 - Thu, Sep 4
PBI
West Palm Beach
MDW
Chicago
$220 Roundtrip, found 3 days ago
$220
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Mon, Aug 4 from West Palm Beach to Chicago, returning Thu, Sep 4, priced at $220 found 3 days ago

Find the cheapest month to fly from West Palm Beach (PBI) to Chicago (MDW)

December is typically the cheapest month to fly

From $128 - $778 per traveler.

Graph displaying average flight prices per month

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $283
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $283
Flights from West Palm Beach (PBI) to Chicago (MDW)
Origin airport
Palm Beach Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$202
Distance
1129 mi

West Palm Beach to Chicago Flights

The cheapest times to fly from West Palm Beach to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from West Palm Beach to Chicago are during the month of July. You can find some of the cheapest flights from West Palm Beach to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from West Palm Beach to Chicago

Sunday is one of the best days to book for cheap flights from West Palm Beach to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from West Palm Beach to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from West Palm Beach to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $104 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap West Palm Beach to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your West Palm Beach to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from PBI to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from PBI to MDW?
The cheapest flights from PBI to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
There are no direct flights from West Palm Beach, FL (PBI-Palm Beach Intl.) to Midway Intl. Airport (MDW). However, you can find other airports that offer nonstop flights. Begin your journey at Fort Lauderdale - Hollywood Intl. Airport (FLL) and head straight to Chicago without any detours.
What is the cheapest airline that flies from PBI to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from PBI to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
There aren't any daily nonstop flights from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW). But you can opt for flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time.
What day of the week has the most flights from PBI to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays are often the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
To arrive at Midway Intl. Airport (MDW) without delays, select a flight that leaves from Palm Beach Intl. Airport (PBI) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Palm Beach Intl. Airport (PBI)?
If you're boarding a direct flight from Palm Beach Intl. Airport (PBI) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can land at.
Is it cheaper to buy a plane ticket from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW) last-minute?
Booking your plane ticket from PBI to MDW right before your journey is typically more expensive. However, if you're flexible with your travel dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a PBI to MDW flight and hotel package?
You'll typically save money by securing a PBI to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. Once you've selected your ideal accommodations and flights, you can add extras such as tours, car rentals and activities.
Can I cancel or change the date of my flight from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
If you booked your PBI to MDW flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal if you'd like more information.

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*Available to One Key members.