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$75+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$210
(Southwest)

One-way from

$75
(Southwest)

Popular in

June

Cheapest in

January

Average price

$390
From Palm Beach Intl to Chicago Midway
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One-way flight from Palm Beach Intl to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/10. 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.
Sat 10/184:35 pmPBI - MDW
1 stop5h 20mSouthwest
Tue 10/218:40 amMDW - PBI
1 stop6h 15mSouthwest
Deal found 9/10$210
This Southwest deal was found by Cheapflights users on 9/9. 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.
Tue 10/77:00 amPBI - MDW
2 stops6h 10mSouthwest
Tue 10/1412:40 pmMDW - PBI
2 stops8h 10mSouthwest
Deal found 9/9$212
This Delta deal was found by Cheapflights users on 9/9. 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.
Fri 10/246:13 pmPBI - MDW
1 stop5h 01mDelta
Mon 10/2710:35 amMDW - PBI
1 stop7h 02mDelta
Deal found 9/9$217
This Southwest deal was found by Cheapflights users on 9/9. 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.
Wed 12/37:05 amPBI - MDW
2 stops8h 50mSouthwest
Fri 12/56:40 amMDW - PBI
1 stop9h 45mSouthwest
Deal found 9/9$219
This Southwest deal was found by Cheapflights users on 9/11. 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.
Sun 10/126:45 pmPBI - MDW
1 stop5h 25mSouthwest
Tue 10/146:10 amMDW - PBI
1 stop8h 45mSouthwest
Deal found 9/11$220
This Southwest deal was found by Cheapflights users on 9/9. 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.
Fri 10/2411:25 amPBI - MDW
1 stop7h 15mSouthwest
Mon 10/275:00 amMDW - PBI
1 stop6h 20mSouthwest
Deal found 9/9$222
This CheapOair deal was found by Cheapflights users on 9/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/221:12 pmPBI - MDW
1 stop27h 46mFrontier
Thu 9/254:56 pmMDW - PBI
1 stop18h 21mFrontier
Deal found 9/9$224
This Cheapflightsfares deal was found by Cheapflights users on 9/9. 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.
Fri 11/71:48 pmPBI - MDW
1 stop5h 51mFrontier
Mon 11/106:15 amMDW - PBI
1 stop5h 13mFrontier
Deal found 9/9$227
This Southwest deal was found by Cheapflights users on 9/11. 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.
Wed 10/155:45 pmPBI - MDW
1 stop5h 50mSouthwest
Thu 10/1611:25 amMDW - PBI
1 stop8h 40mSouthwest
Deal found 9/11$229
This Frontier deal was found by Cheapflights users on 9/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/191:12 pmPBI - MDW
1 stop11h 08mFrontier
Mon 9/226:20 amMDW - PBI
1 stop4h 57mFrontier
Deal found 9/9$231
This Delta deal was found by Cheapflights users on 9/10. 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.
Tue 11/255:31 pmPBI - MDW
1 stop7h 01mDelta
Thu 11/276:00 amMDW - PBI
1 stop4h 58mDelta
Deal found 9/10$234

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 September 11, 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

Sat 10/18

4:35 pm-8:55 pm

1 stop5h 20m

Chicago Midway

Tue 10/21

8:40 am-3:55 pm

1 stop6h 15m

$210

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 10/7

7:00 am-12:10 pm

2 stops6h 10m

Chicago Midway

Tue 10/14

12:40 pm-9:50 pm

2 stops8h 10m

$212

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 2/27

3:30 pm-9:46 pm

1 stop7h 16m

Chicago Midway

Tue 3/3

5:25 pm-12:13 am

1 stop5h 48m

$217

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 12/4

6:48 pm-11:32 pm

1 stop5h 44m

Chicago Midway

Mon 12/8

6:00 am-1:12 pm

1 stop6h 12m

$217

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 10/22

6:13 pm-10:14 pm

1 stop5h 01m

Chicago Midway

Tue 11/4

10:40 am-6:37 pm

1 stop6h 57m

$217

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 10/24

6:13 pm-10:14 pm

1 stop5h 01m

Chicago Midway

Mon 10/27

10:35 am-6:37 pm

1 stop7h 02m

$217

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 12/3

7:05 am-2:55 pm

2 stops8h 50m

Chicago Midway

Fri 12/5

6:40 am-5:25 pm

1 stop9h 45m

$219

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 10/12

6:45 pm-11:10 pm

1 stop5h 25m

Chicago Midway

Tue 10/14

6:10 am-3:55 pm

1 stop8h 45m

$220

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 10/24

11:25 am-5:40 pm

1 stop7h 15m

Chicago Midway

Mon 10/27

5:00 am-12:20 pm

1 stop6h 20m

$222

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 11/11

6:30 am-1:00 pm

2 stops7h 30m

Chicago Midway

Wed 11/12

1:25 pm-9:55 pm

2 stops7h 30m

$227

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 20 results
1
2

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 September 11, 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 September 11, 2025.
See what other customers who have flown with Southwest and Delta 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
4,248 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Boarding

8.1

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

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.

  • How long is the flight from West Palm Beach to Chicago Midway Airport?

    Airlines like Southwest and Delta fly from West Palm Beach to Chicago Midway Airport in about 5h 20m. The time it takes to get you to your destination can typically vary by up to 1h 56m. The distance between West Palm Beach and Chicago Midway Airport is about 1129 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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 $149. Another airline that can offer you cheap pricing is Delta. Users have found that Southwest is 54% cheaper than the other options available to this destination.

  • 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
Chesterton

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Alternative routes for West Palm Beach to Midway

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$149Average$288FlexibilityNo cancel feeOn-time63%
DeltaCheapest$232Average$361FlexibilityNo cancel feeOn-timeN/A

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