$77 Cheap Flights from West Palm Beach (PBI) to Chicago (MDW)

View $77 flight on Mon, Nov 10, 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 $77 for one-way flights and $153 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Mon, Nov 10 - Mon, Nov 17
PBI
West Palm Beach
MDW
Chicago
$153 Roundtrip, found 1 hour ago
$153
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Mon, Nov 10 from West Palm Beach to Chicago, returning Mon, Nov 17, priced at $153 found 1 hour ago
Frontier Airlines
Fri, Oct 3 - Mon, Oct 6
PBI
West Palm Beach
MDW
Chicago
$154 Roundtrip, found 4 hours ago
$154
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Fri, Oct 3 from West Palm Beach to Chicago, returning Mon, Oct 6, priced at $154 found 4 hours ago
Frontier Airlines
Thu, Oct 9 - Sun, Oct 12
PBI
West Palm Beach
MDW
Chicago
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Thu, Oct 9 from West Palm Beach to Chicago, returning Sun, Oct 12, priced at $164 found 7 hours ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
PBI
West Palm Beach
MDW
Chicago
$195 Roundtrip, found 3 hours ago
$195
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Sep 26 from West Palm Beach to Chicago, returning Mon, Sep 29, priced at $195 found 3 hours ago
Southwest Airlines
Wed, Oct 29 - Fri, Oct 31
PBI
West Palm Beach
MDW
Chicago
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from West Palm Beach to Chicago, returning Fri, Oct 31, priced at $197 found 5 days ago
Southwest Airlines
Wed, Oct 22 - Sun, Oct 26
PBI
West Palm Beach
MDW
Chicago
$198 Roundtrip, found 16 hours ago
$198
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Wed, Oct 22 from West Palm Beach to Chicago, returning Sun, Oct 26, priced at $198 found 16 hours ago
Southwest Airlines
Wed, Oct 8 - Sun, Oct 12
PBI
West Palm Beach
MDW
Chicago
$201 Roundtrip, found 6 days ago
$201
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Wed, Oct 8 from West Palm Beach to Chicago, returning Sun, Oct 12, priced at $201 found 6 days ago
Frontier Airlines
Fri, Nov 14 - Mon, Nov 17
PBI
West Palm Beach
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Nov 14 from West Palm Beach to Chicago, returning Mon, Nov 17, priced at $203 found 2 days ago
Southwest Airlines
Wed, Oct 15 - Sun, Oct 19
PBI
West Palm Beach
MDW
Chicago
$203 Roundtrip, found 2 days ago
$203
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Wed, Oct 15 from West Palm Beach to Chicago, returning Sun, Oct 19, priced at $203 found 2 days ago
Delta
Wed, Oct 22 - Sun, Oct 26
PBI
West Palm Beach
MDW
Chicago
$239 Roundtrip, found 16 hours ago
$239
Roundtrip
found 16 hours ago
Select Delta flight, departing Wed, Oct 22 from West Palm Beach to Chicago, returning Sun, Oct 26, priced at $239 found 16 hours 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 - $784 per traveler.

Frequently asked questions

How much does a flight from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW) cost?
Lock in a cheap one-way flight from $77 or cheap return flight from $153 from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
The cheapest month to fly from PBI to MDW is November, when demand is low. Off-peak season is often when you'll find lower airfares between these airports.
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 Palm Beach Intl. Airport (PBI) to Midway Intl. Airport (MDW)?
Use the filter tool on Expedia to compare different airlines and find the cheapest carrier that'll take you from PBI to MDW. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
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.

Travel information

Travel information

Origin airport
Palm Beach Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$152
Distance
1129 mi

Book with confidence

Book with confidence

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 November. 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 $77 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.

 

West Palm Beach to Chicago Flights

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*Available to One Key members.