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Cheap flights from West Palm Beach to Chicago from $55

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from West Palm Beach to Chicago departing on 11/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
12:45 pm - 6:20 pmPBI-MDW
6h 35m1 stop
Frontier Logo
6:00 am - 12:41 pmMDW-PBI
5h 41m1 stop
$210Frontier
Find Deal
Wed, Nov 26 - Thu, Jan 8
Frontier Logo
12:45 pm - 7:31 pmPBI-MDW
7h 46m1 stop
Frontier Logo
6:05 am - 12:24 pmMDW-PBI
5h 19m1 stop
$212Frontier
Find Deal
Thu, Nov 20 - Tue, Nov 25
Multiple Airlines Logo
3:53 pm - 10:43 pmPBI-MDW
7h 50m1 stop
Multiple Airlines Logo
7:44 am - 10:55 pmMDW-PBI
14h 11m1 stop
$213Multiple Airlines
Find Deal
Thu, Nov 27 - Sun, Jan 4
Frontier Logo
1:19 pm - 10:03 pmPBI-MDW
9h 44m1 stop
Frontier Logo
6:00 am - 10:09 amMDW-PBI
27h 09m2 stops
$222Frontier
Find Deal
Tue, Nov 25 - Wed, Jan 7
Frontier Logo
6:05 pm - 2:04 pmPBI-MDW
20h 59m2 stops
Frontier Logo
6:15 am - 5:59 pmMDW-PBI
10h 44m1 stop
$223Frontier
Find Deal
Thu, Dec 11 - Sun, Dec 14
Multiple Airlines Logo
3:53 pm - 10:43 pmPBI-MDW
7h 50m1 stop
Multiple Airlines Logo
3:10 pm - 1:56 pmMDW-PBI
21h 46m2 stops
$235Multiple Airlines
Find Deal
Thu, Nov 27 - Mon, Jan 5
Delta Logo
6:35 pm - 11:40 pmPBI-MDW
6h 05m1 stop
Delta Logo
5:31 pm - 12:16 amMDW-PBI
5h 45m1 stop
$249Delta
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Wed, Nov 26 - Tue, Jan 6
Southwest Logo
11:25 am - 10:05 pmPBI-MDW
11h 40m1 stop
Southwest Logo
5:00 am - 11:45 amMDW-PBI
5h 45m1 stop
$254Southwest
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Mon, Jan 26 - Wed, Jan 28
Southwest Logo
7:05 am - 12:30 pmPBI-MDW
6h 25m2 stops
Southwest Logo
1:35 pm - 9:30 pmMDW-PBI
6h 55m2 stops
$259Southwest
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Thu, Jan 8 - Sun, Jan 11
Delta Logo
8:00 am - 11:52 amPBI-MDW
4h 52m1 stop
Delta Logo
11:21 am - 5:06 pmMDW-PBI
4h 45m1 stop
$274Delta
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Sun, Nov 23 - Wed, Jan 7

Southwest flights from West Palm Beach to Chicago Midway Airport

Our best Southwest deals on West Palm Beach to Chicago Midway Airport flight tickets
Southwest
Jan 26
PBI11:25 amPalm Beach Intl
11h 40m
1 stop
MDW10:05 pmChicago Midway
Jan 28
MDW5:00 amChicago Midway
5h 45m
1 stop
PBI11:45 amPalm Beach Intl
$254
Find similar
Southwest
Jan 8
PBI7:05 amPalm Beach Intl
6h 25m
2 stops
MDW12:30 pmChicago Midway
Jan 11
MDW1:35 pmChicago Midway
6h 55m
2 stops
PBI9:30 pmPalm Beach Intl
$259
Find similar
Southwest
Jan 26
PBI11:25 amPalm Beach Intl
11h 40m
1 stop
MDW10:05 pmChicago Midway
Jan 28
MDW6:00 amChicago Midway
9h 25m
2 stops
PBI4:25 pmPalm Beach Intl
$260
Find similar

Frontier flights from West Palm Beach to Chicago Midway Airport

Our best Frontier deals on West Palm Beach to Chicago Midway Airport flight tickets
Frontier
Nov 26
PBI12:45 pmPalm Beach Intl
6h 35m
1 stop
MDW6:20 pmChicago Midway
Jan 8
MDW6:00 amChicago Midway
5h 41m
1 stop
PBI12:41 pmPalm Beach Intl
$210
Find similar
Frontier
Nov 20
PBI12:45 pmPalm Beach Intl
7h 46m
1 stop
MDW7:31 pmChicago Midway
Nov 25
MDW6:05 amChicago Midway
5h 19m
1 stop
PBI12:24 pmPalm Beach Intl
$212
Find similar
Frontier
Nov 25
PBI1:19 pmPalm Beach Intl
9h 44m
1 stop
MDW10:03 pmChicago Midway
Jan 7
MDW6:00 amChicago Midway
27h 09m
2 stops
PBI10:09 amPalm Beach Intl
$222
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from West Palm Beach to Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated November 5, 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

Fly to

Route

Depart

Return

Price

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 11/26

12:45 pm-6:20 pm

1 stop6h 35m

Chicago Midway

Thu 1/8

6:00 am-12:41 pm

1 stop5h 41m

$210

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 11/20

12:45 pm-7:31 pm

1 stop7h 46m

Chicago Midway

Tue 11/25

6:05 am-12:24 pm

1 stop5h 19m

$212

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 11/27

3:53 pm-10:43 pm

1 stop7h 50m

Chicago Midway

Sun 1/4

7:44 am-10:55 pm

1 stop14h 11m

$213

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 11/25

1:19 pm-10:03 pm

1 stop9h 44m

Chicago Midway

Wed 1/7

6:00 am-10:09 am

2 stops27h 09m

$222

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 12/11

6:05 pm-2:04 pm

2 stops20h 59m

Chicago Midway

Sun 12/14

6:15 am-5:59 pm

1 stop10h 44m

$223

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 11/27

3:53 pm-10:43 pm

1 stop7h 50m

Chicago Midway

Mon 1/5

3:10 pm-1:56 pm

2 stops21h 46m

$235

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 11/26

6:35 pm-11:40 pm

1 stop6h 05m

Chicago Midway

Tue 1/6

5:31 pm-12:16 am

1 stop5h 45m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Mon 1/26

11:25 am-10:05 pm

1 stop11h 40m

Chicago Midway

Wed 1/28

5:00 am-11:45 am

1 stop5h 45m

$254

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 1/8

7:05 am-12:30 pm

2 stops6h 25m

Chicago Midway

Sun 1/11

1:35 pm-9:30 pm

2 stops6h 55m

$259

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 11/23

8:00 am-11:52 am

1 stop4h 52m

Chicago Midway

Wed 1/7

11:21 am-5:06 pm

1 stop4h 45m

$274

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from West Palm Beach to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from West Palm Beach, with most prices found around $118. If you are unable to visit Chicago Midway Airport during the month of January, then departing from West Palm Beach during the month February is also very affordable. Most momondo users find prices during this month for around $216.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Sunday is the cheapest day to fly to Chicago Midway Airport from West Palm Beach. The lowest ticket price found for a Sunday departure recently was $240. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from West Palm Beach because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $434.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from West Palm Beach in the morning is the least expensive time of day to depart. momondo users have found prices as low as $358 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $413. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from West Palm Beach to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from West Palm Beach to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap West Palm Beach to Chicago Midway Airport (PBI to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from West Palm Beach to Chicago Midway Airport

Direct flights

None
There are no direct flights from West Palm Beach to Chicago Midway Airport. There are no popular flight routes from West Palm Beach to Chicago Midway Airport.
Search flight deals

  • How far is Palm Beach Intl to Chicago Midway by plane?

    Palm Beach Intl and Chicago Midway are 1128.6 mi apart from one another. Typically, this will take 4h 50m by plane in normal conditions.

  • When did momondo last update prices for flights from Palm Beach Intl Airport to Chicago Midway Airport?

    Prices for flights from Palm Beach Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Palm Beach Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Palm Beach Intl Airport to Chicago Midway Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Palm Beach Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular airline from West Palm Beach to Chicago Midway Airport?

Best airlines flying from West Palm Beach to Chicago Midway Airport

Compare and see reviews for airlines that fly from West Palm Beach to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $149Free CancellationRating
8.0
4,240 reviews
Search Southwest flights
DeltaPriceFrom $232Free CancellationRating
7.9
8,004 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from West Palm Beach to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from West Palm Beach to Chicago for you.

Can I find flights from West Palm Beach to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from West Palm Beach on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from West Palm Beach to Chicago?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from West Palm Beach to Chicago.

I’m not ready to book a flight from West Palm Beach to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for West Palm Beach to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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