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$55+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — MDW
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$211
(Frontier)

One-way from

$55
(CheapOair)

Popular in

June

Cheapest in

January

Average price

$384
Provider with most accurate pricing for Palm Beach Intl-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Palm Beach Intl-Chicago Midway flights.
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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. 7% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:48 pmPBI - MDW
1 stop9h 23mFrontier
Tue 11/256:05 amMDW - PBI
1 stop5h 19mFrontier
Deal found 10/29$211
This CheapOair deal was found by Cheapflights users on 10/30. 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.
Fri 11/71:23 pmPBI - MDW
1 stop9h 45mFrontier
Sun 12/146:15 amMDW - PBI
1 stop10h 44mFrontier
Deal found 10/30$213
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/273:53 pmPBI - MDW
1 stop7h 50mFrontier
Thu 1/86:00 amMDW - PBI
1 stop5h 41mFrontier
Deal found 10/28$219
This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/311:23 pmPBI - MDW
1 stop9h 22mFrontier
Mon 11/36:20 amMDW - PBI
1 stop5h 08mFrontier
Deal found 10/28$228
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/251:19 pmPBI - MDW
1 stop9h 44mFrontier
Thu 1/86:00 amMDW - PBI
1 stop5h 41mFrontier
Deal found 10/29$230
This Frontier deal was found by Cheapflights users on 10/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:48 pmPBI - MDW
1 stop9h 23mFrontier
Sun 11/236:05 amMDW - PBI
1 stop8h 49mFrontier
Deal found 10/28$231
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/237:00 amPBI - MDW
2 stops34h 52mMultiple Airlines
Thu 1/86:00 amMDW - PBI
1 stop5h 41mMultiple Airlines
Deal found 10/30$233
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/36:49 pmPBI - MDW
2 stops28h 09mMultiple Airlines
Thu 12/116:15 amMDW - PBI
1 stop9h 57mMultiple Airlines
Deal found 10/30$237
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/273:53 pmPBI - MDW
1 stop7h 50mMultiple Airlines
Mon 1/53:10 pmMDW - PBI
2 stops21h 46mMultiple Airlines
Deal found 10/30$247
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/2012:45 pmPBI - MDW
1 stop7h 46mFrontier
Sun 11/236:05 amMDW - PBI
1 stop8h 49mFrontier
Deal found 10/29$248
This Delta deal was found by Cheapflights users on 10/30. 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.
Sat 11/226:35 pmPBI - MDW
1 stop6h 05mDelta
Wed 1/76:45 amMDW - PBI
1 stop5h 31mDelta
Deal found 10/30$249

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 October 30, 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 11/22

5:31 pm-11:40 pm

1 stop7h 09m

Chicago Midway

Wed 11/26

12:47 pm-8:59 pm

1 stop7h 12m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 11/22

6:35 pm-11:40 pm

1 stop6h 05m

Chicago Midway

Tue 1/6

6:45 am-1:16 pm

1 stop5h 31m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 11/22

5:31 pm-11:40 pm

1 stop7h 09m

Chicago Midway

Sat 1/3

4:25 pm-10:08 pm

1 stop4h 43m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 11/23

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

Sat 1/3

6:00 am-11:52 am

1 stop4h 52m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 11/21

6:35 pm-11:40 pm

1 stop6h 05m

Chicago Midway

Sat 11/22

4:28 pm-12:35 am

1 stop7h 07m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 12/2

7:48 pm-11:47 pm

1 stop4h 59m

Chicago Midway

Wed 12/17

6:00 am-12:02 pm

1 stop5h 02m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 11/22

6:35 pm-11:40 pm

1 stop6h 05m

Chicago Midway

Thu 11/27

10:47 am-4:33 pm

1 stop4h 46m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 11/19

7:00 am-11:52 am

1 stop5h 52m

Chicago Midway

Thu 11/27

10:47 am-4:33 pm

1 stop4h 46m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 11/22

5:31 pm-11:40 pm

1 stop7h 09m

Chicago Midway

Sun 11/23

5:34 pm-11:24 pm

1 stop4h 50m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 12/4

6:35 pm-11:47 pm

1 stop6h 12m

Chicago Midway

Sun 12/7

6:00 am-12:02 pm

1 stop5h 02m

$249

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 results
1
2

Compare providers for flights from West Palm Beach to Midway

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from West Palm Beach to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on West Palm Beach-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on West Palm Beach-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from West Palm Beach-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on West Palm Beach-Chicago Midway Airport flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for West Palm Beach-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, September is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $72). Flying from West Palm Beach to Chicago Midway Airport in August is currently the most expensive (average of $197). 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 October 30, 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 evening. If you’re flexible enough to do this you can expect to save up to 71% 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 October 30, 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
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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
7.9
Good
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Comfort

8.0

Boarding

8.1

Food

7.0

Overall

8.0

Entertainment

7.5

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.

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

    Airlines like Delta fly from West Palm Beach to Chicago Midway Airport in about 7h 09m. The time it takes to get you to your destination can typically vary by up to . The distance between West Palm Beach and Chicago Midway Airport is about 1129 mi.

  • 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 52% 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, September is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $72). Flying from West Palm Beach to Chicago Midway Airport in August is currently the most expensive (average of $197). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$149Average$413FlexibilityNo cancel feeOn-time63%
DeltaCheapest$232Average$358FlexibilityNo cancel feeOn-timeN/A

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