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Midway

$150+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — MDW
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/1211:32 am
PBI
-
MDW
2 stops11h 47m
Multiple Airlines
Tue 3/177:30 am
MDW
-
PBI
1 stop28h 30m
Multiple Airlines
Deal found 1/27$242
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 2/271:16 pm
PBI
-
MDW
1 stop6h 22m
Frontier
Fri 3/69:51 pm
MDW
-
PBI
2 stops22h 31m
Frontier
Deal found 1/28$245
This Delta deal was found by Cheapflights users on 1/26. 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 4/244:52 pm
PBI
-
MDW
1 stop6h 36m
Delta
Sun 4/266:00 am
MDW
-
PBI
1 stop4h 45m
Delta
Deal found 1/26$249
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/201:09 pm
PBI
-
MDW
1 stop5h 44m
Frontier
Sun 2/226:00 am
MDW
-
PBI
1 stop5h 17m
Frontier
Deal found 1/26$250
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/63:34 pm
PBI
-
MDW
1 stop7h 45m
Frontier
Mon 2/96:20 am
MDW
-
PBI
1 stop7h 14m
Frontier
Deal found 1/27$256
This Frontier deal was found by Cheapflights users on 1/28. 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 2/231:27 pm
PBI
-
MDW
1 stop7h 20m
Frontier
Fri 2/276:00 am
MDW
-
PBI
1 stop5h 21m
Frontier
Deal found 1/28$259
This Kiwi.com deal was found by Cheapflights users on 1/29. 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.
Thu 2/199:23 am
PBI
-
MDW
2 stops14h 14m
Multiple Airlines
Sun 2/229:04 pm
MDW
-
PBI
1 stop14h 28m
Multiple Airlines
Deal found 1/29$263
This Delta deal was found by Cheapflights users on 1/28. 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.
Fri 3/66:00 am
PBI
-
MDW
1 stop4h 54m
Delta
Sun 3/86:00 am
MDW
-
PBI
1 stop4h 43m
Delta
Deal found 1/28$269
This Southwest deal was found by Cheapflights users on 1/27. 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.
Wed 2/117:30 am
PBI
-
MDW
1 stop8h 25m
Southwest
Wed 2/185:00 am
MDW
-
PBI
1 stop5h 45m
Southwest
Deal found 1/27$274

Find 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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$242
(Kiwi.com)

One-way from

$150
(Southwest)

Popular in

June

Cheapest in

October

Average price

$358
Provider with most accurate pricing for Palm Beach Intl-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for Palm Beach Intl-Chicago Midway flights.
Search Deals
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. 4% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 29, 2026.
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 4/24

12:45 pm-5:58 pm

1 stop6h 13m

Chicago Midway

Sat 4/25

5:21 pm-12:40 am

1 stop6h 19m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 5/23

4:45 pm-9:45 pm

1 stop6h 00m

Chicago Midway

Mon 5/25

6:00 am-1:01 pm

1 stop6h 01m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 3/6

6:00 am-9:54 am

1 stop4h 54m

Chicago Midway

Sun 3/8

6:00 am-11:43 am

1 stop4h 43m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 3/31

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Sat 4/4

9:35 am-5:52 pm

1 stop7h 17m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 4/11

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Mon 4/13

5:21 pm-11:07 pm

1 stop4h 46m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 3/19

12:59 pm-5:54 pm

1 stop5h 55m

Chicago Midway

Wed 3/25

6:07 pm-12:32 am

1 stop5h 25m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 2/19

12:55 pm-5:45 pm

1 stop5h 50m

Chicago Midway

Sun 2/22

6:40 pm-12:37 am

1 stop4h 57m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 4/24

4:52 pm-10:28 pm

1 stop6h 36m

Chicago Midway

Sun 4/26

6:00 am-11:45 am

1 stop4h 45m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 2/20

1:09 pm-5:53 pm

1 stop5h 44m

Chicago Midway

Sun 2/22

6:00 am-12:17 pm

1 stop5h 17m

$250

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 2/19

9:23 am-10:37 pm

2 stops14h 14m

Chicago Midway

Sun 2/22

9:04 pm-12:32 pm

1 stop14h 28m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

Showing 1-10 of 22 results
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2
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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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on West Palm Beach-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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, January is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $58). Flying from West Palm Beach to Chicago Midway Airport in August is currently the most expensive (average of $195). 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.

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 January 29, 2026.
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
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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
7.9
Good
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

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 Delta fly from West Palm Beach to Chicago Midway Airport in about 6h 13m. 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 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, January is the cheapest month in which you can book a flight from West Palm Beach to Chicago Midway Airport (average of $58). Flying from West Palm Beach to Chicago Midway Airport in August is currently the most expensive (average of $195). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$149Average$448FlexibilityNo cancel feeOn-time63%
DeltaCheapest$248Average$328FlexibilityNo cancel feeOn-timeN/A

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