HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$108+ Cheap flights from West Palm Beach (PBI) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — MDW
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from West Palm Beach to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from West Palm Beach to Midway

Discover tips and strategies to find the most affordable flight options for your journey from West Palm Beach (PBI) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 29, 2025.

Round-trip from

$238
(Frontier)

One-way from

$108
(Cheapflightsfares)

Popular in

June

Cheapest in

January

Average price

$271
From Palm Beach Intl to Chicago Midway
Search Deals
One-way flight from Palm Beach Intl to Chicago Midway
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

Find flight deals from West Palm Beach to Midway

Cheapest flights from West Palm Beach to Midway
Explore the most affordable flight options available from West Palm Beach to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/46:48 pmPBI - MDW
1 stop5h 29mFrontier
Mon 9/86:20 amMDW - PBI
1 stop4h 57mFrontier
Deal found 7/29$236
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:19 pmPBI - MDW
1 stop7h 18mDelta
Wed 9/310:31 amMDW - PBI
1 stop4h 23mDelta
Deal found 7/28$251
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/146:25 amPBI - MDW
1 stop6h 50mSouthwest
Sun 8/173:20 pmMDW - PBI
1 stop4h 30mSouthwest
Deal found 7/27$253

Cheapflights Fare Finder

 
Customize your flight search to find flights from West Palm Beach to Midway 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, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
Use the filters below to find and compare flights from West Palm Beach to Chicago Midway Airport that are best for you.

Fly from

West Palm Beach

Fly to

Midway

Route

Depart

Return

Price

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 8/22

7:10 pm-11:27 pm

1 stop5h 17m

Chicago Midway

Mon 8/25

6:15 am-6:25 pm

1 stop11h 10m

$238

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 8/27

12:19 pm-6:37 pm

1 stop7h 18m

Chicago Midway

Wed 9/3

10:31 am-3:54 pm

1 stop4h 23m

$251

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 8/14

6:25 am-12:15 pm

1 stop6h 50m

Chicago Midway

Sun 8/17

3:20 pm-8:50 pm

1 stop4h 30m

$253

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 8/29

7:10 pm-11:27 pm

1 stop5h 17m

$108

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 8/31

5:10 pm-9:12 pm

1 stop5h 02m

$126

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 8/20

7:30 am-11:45 am

1 stop5h 15m

$130

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from West Palm Beach to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from West Palm Beach with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from West Palm Beach to Chicago Midway Airport

What is the cheapest month to book a flight from West Palm Beach to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $160). Flying from West Palm Beach to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PBI to MDW?

Find hourly flight availability from West Palm Beach to Midway. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

A simple way to save on the total cost of your ticket is to fly from West Palm Beach to Chicago Midway Airport in the morning. If you’re flexible enough to do this you can expect to save up to 14% on your trip compared to booking a flight at noon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated July 29, 2025.
See what other customers who have flown with Southwest, Delta, and Frontier from West Palm Beach to Chicago Midway Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Frontier
5.9
Fair
3,238 reviews
Southwest
8.0
Very good
4,238 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from West Palm Beach to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from West Palm Beach to Chicago Midway?

    Located just 3.1 mi from the city center, Palm Beach Intl is the airport most travelers will use when flying to Chicago Midway from West Palm Beach. Booking flights from Palm Beach Intl (PBI) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 2 different airlines.

  • What are the cheapest airlines flying from West Palm Beach to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from West Palm Beach to Chicago Midway Airport round-trip from $238. Other airlines that can offer you cheap pricing are Delta, from $251, and Southwest, from $253. Users have found that Frontier is 27% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from West Palm Beach to Chicago Midway Airport one-way?

    $108 is the cheapest one-way deal found within the past few days, from Frontier. You may also be able to find cheap deals on Delta and Southwest, with prices starting from $126 and $130, respectively.

  • Can I find deals for flights from West Palm Beach to Midway that include hotel bookings?

    Yes. In addition to deals on West Palm Beach to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from West Palm Beach to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from West Palm Beach to Midway.

  • Can I find deals for business class flights from West Palm Beach to Midway?

    Yes. Cheapflights offers flight deals from West Palm Beach to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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

    Currently, April is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $160). Flying from West Palm Beach to Chicago Midway Airport in November is currently the most expensive (average of $249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for West Palm Beach to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Orlando to O'Hare Intl flights
Fort Lauderdale to O'Hare Intl flights
Miami to O'Hare Intl flights
Tampa to O'Hare Intl flights
West Palm Beach to O'Hare Intl flights
Orlando to Midway flights
Miami to Midway flights
Jacksonville to O'Hare Intl flights
Tampa to Midway flights
Fort Myers to O'Hare Intl flights
Pensacola to O'Hare Intl flights
Fort Lauderdale to Midway flights
Sarasota to O'Hare Intl flights
Jacksonville to Midway flights
Panama City to O'Hare Intl flights
Pensacola to Midway flights
Sarasota to Midway flights
Fort Myers to Midway flights
Daytona Beach to O'Hare Intl flights
St Petersburg to Rockford flights
Fort Lauderdale to Rockford flights
Tallahassee to O'Hare Intl flights
Panama City to Midway flights
Valparaiso to O'Hare Intl flights
Daytona Beach to Midway flights
Gainesville to O'Hare Intl flights
Key West to O'Hare Intl flights
Tallahassee to Midway flights
Orlando Sanford Intl to Rockford flights
Melbourne to O'Hare Intl flights
Gainesville to Midway flights
Valparaiso to Midway flights
Tampa to Rockford flights
Key West to Midway flights
Valdosta to O'Hare Intl flights
Melbourne to Midway flights
Orlando to Rockford flights
Punta Gorda to Rockford flights
Fort Myers to Rockford flights
Pensacola to Rockford flights

Top 2 airlines flying from West Palm Beach to Midway

Discover the top 2 airlines that operate flights from West Palm Beach to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$149Average$288FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$359FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.