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Cheap flights from West Palm Beach to Chicago from $147

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 5/2. 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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0 bags

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Find the cheapest flights from West Palm Beach to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
3:10 pm - 9:00 pm
PBI
-
MDW
6h 50m
1 stop
Southwest Logo
12:00 pm - 5:45 pm
MDW
-
PBI
4h 45m
1 stop
$249Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
5:50 pm - 12:05 am
PBI
-
MDW
7h 15m
1 stop
Southwest Logo
9:10 am - 5:20 pm
MDW
-
PBI
7h 10m
2 stops
$250Southwest
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
4:15 pm - 10:20 pm
PBI
-
MDW
7h 05m
1 stop
Southwest Logo
8:00 am - 5:45 pm
MDW
-
PBI
8h 45m
2 stops
$254Southwest
Thu, Apr 23 - Mon, Apr 27
Southwest Logo
5:50 pm - 11:30 pm
PBI
-
MDW
6h 40m
2 stops
Southwest Logo
9:10 am - 5:20 pm
MDW
-
PBI
7h 10m
2 stops
$255Southwest
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
4:15 pm - 9:55 pm
PBI
-
MDW
6h 40m
2 stops
Southwest Logo
12:45 pm - 9:50 pm
MDW
-
PBI
8h 05m
2 stops
$259Southwest
Tue, Mar 31 - Tue, Apr 7
Delta Logo
2:40 pm - 9:09 pm
PBI
-
MDW
7h 29m
1 stop
Delta Logo
5:10 pm - 11:44 pm
MDW
-
PBI
5h 34m
1 stop
$260Delta
Sat, May 16 - Tue, May 19
Southwest Logo
5:50 pm - 12:05 am
PBI
-
MDW
7h 15m
1 stop
Southwest Logo
12:50 pm - 9:20 pm
MDW
-
PBI
7h 30m
2 stops
$267Southwest
Fri, Apr 24 - Tue, Apr 28
Delta Logo
6:00 am - 9:56 am
PBI
-
MDW
4h 56m
1 stop
Delta Logo
6:07 pm - 12:32 am
MDW
-
PBI
5h 25m
1 stop
$269Delta
Fri, Mar 27 - Mon, Mar 30
Southwest Logo
6:20 am - 12:20 pm
PBI
-
MDW
7h 00m
2 stops
Southwest Logo
12:00 pm - 9:55 pm
MDW
-
PBI
8h 55m
2 stops
$270Southwest
Thu, Apr 23 - Mon, Apr 27
Delta Logo
6:10 pm - 9:45 pm
PBI
-
MDW
4h 35m
1 stop
Delta Logo
10:35 am - 6:46 pm
MDW
-
PBI
7h 11m
1 stop
$271Delta
Sat, Jun 27 - Sat, Jul 11

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
Apr 23
PBI3:10 pmPalm Beach Intl
6h 50m
1 stop
MDW9:00 pmChicago Midway
Apr 27
MDW12:00 pmChicago Midway
4h 45m
1 stop
PBI5:45 pmPalm Beach Intl
$249
Southwest
Apr 24
PBI5:50 pmPalm Beach Intl
7h 15m
1 stop
MDW12:05 amChicago Midway
Apr 28
MDW9:10 amChicago Midway
7h 10m
2 stops
PBI5:20 pmPalm Beach Intl
$250
Southwest
Apr 23
PBI4:15 pmPalm Beach Intl
7h 05m
1 stop
MDW10:20 pmChicago Midway
Apr 27
MDW8:00 amChicago Midway
8h 45m
2 stops
PBI5:45 pmPalm Beach Intl
$254

Delta flights from West Palm Beach to Chicago Midway Airport

Our best Delta deals on West Palm Beach to Chicago Midway Airport flight tickets
Delta
May 16
PBI2:40 pmPalm Beach Intl
7h 29m
1 stop
MDW9:09 pmChicago Midway
May 19
MDW5:10 pmChicago Midway
5h 34m
1 stop
PBI11:44 pmPalm Beach Intl
$260
Delta
Mar 27
PBI6:00 amPalm Beach Intl
4h 56m
1 stop
MDW9:56 amChicago Midway
Mar 30
MDW6:07 pmChicago Midway
5h 25m
1 stop
PBI12:32 amPalm Beach Intl
$269
Delta
Jun 27
PBI6:10 pmPalm Beach Intl
4h 35m
1 stop
MDW9:45 pmChicago Midway
Jul 11
MDW10:35 amChicago Midway
7h 11m
1 stop
PBI6:46 pmPalm Beach Intl
$271

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 March 3, 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

Fly to

Route

Depart

Return

Price

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 4/23

3:10 pm-9:00 pm

1 stop6h 50m

Chicago Midway

Mon 4/27

12:00 pm-5:45 pm

1 stop4h 45m

$249

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 4/24

5:50 pm-12:05 am

1 stop7h 15m

Chicago Midway

Tue 4/28

9:10 am-5:20 pm

2 stops7h 10m

$250

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 4/23

4:15 pm-10:20 pm

1 stop7h 05m

Chicago Midway

Mon 4/27

8:00 am-5:45 pm

2 stops8h 45m

$254

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 4/24

5:50 pm-11:30 pm

2 stops6h 40m

Chicago Midway

Tue 4/28

9:10 am-5:20 pm

2 stops7h 10m

$255

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 3/31

4:15 pm-9:55 pm

2 stops6h 40m

Chicago Midway

Tue 4/7

12:45 pm-9:50 pm

2 stops8h 05m

$259

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 5/16

2:40 pm-9:09 pm

1 stop7h 29m

Chicago Midway

Tue 5/19

5:10 pm-11:44 pm

1 stop5h 34m

$260

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 4/24

5:50 pm-12:05 am

1 stop7h 15m

Chicago Midway

Tue 4/28

12:50 pm-9:20 pm

2 stops7h 30m

$267

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 3/27

6:00 am-9:56 am

1 stop4h 56m

Chicago Midway

Mon 3/30

6:07 pm-12:32 am

1 stop5h 25m

$269

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Thu 4/23

6:20 am-12:20 pm

2 stops7h 00m

Chicago Midway

Mon 4/27

12:00 pm-9:55 pm

2 stops8h 55m

$270

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 6/27

6:10 pm-9:45 pm

1 stop4h 35m

Chicago Midway

Sat 7/11

10:35 am-6:46 pm

1 stop7h 11m

$271

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 airline that flies from Palm Beach Intl to Chicago Midway?

Southwest and Frontier are the most popular carriers operating from Palm Beach Intl to Chicago Midway

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from West Palm Beach according to our data. Southwest is the first choice among our users, with 81% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

Fastest flight time

4h 35m

Direct flights

None
The fastest flight from West Palm Beach to Chicago Midway Airport takes 4h 35m
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 35m 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
4,301 reviews
Search Southwest flights
DeltaPriceFrom $248Free CancellationRating
7.9
8,242 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
Valparaiso
Schererville
Munster
Crown Point
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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