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$122+ Cheap flights from West Palm Beach (PBI) to Chicago (CHI)

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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — CHI
May 23 — May 301
Sat 5/23
Sat 5/30
1 adult, Economy
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Cheapflights Tip: The best prices from Palm Beach Intl to Chicago are usually found in August or October, booked 86 days in advance, depart on a Thursday or Friday and return on a Wednesday

Cheap flight deals from West Palm Beach to Chicago

Cheapest flights from West Palm Beach to Chicago
Explore the most affordable flight options available from West Palm Beach to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.

This Southwest deal was found by Cheapflights users on 4/19. 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 6/27:10 am
PBI
-
MDW
1 stop6h 00m
Southwest
Tue 6/911:50 am
MDW
-
PBI
2 stops9h 20m
Southwest
Deal found 4/19$231
This Southwest deal was found by Cheapflights users on 4/20. 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 5/206:00 pm
PBI
-
ORD
1 stop4h 55m
Southwest
Wed 5/275:55 am
ORD
-
PBI
2 stops14h 25m
Southwest
Deal found 4/20$232
This Southwest deal was found by Cheapflights users on 4/20. 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 8/194:00 pm
PBI
-
MDW
1 stop5h 45m
Southwest
Tue 8/259:25 am
MDW
-
PBI
1 stop5h 55m
Southwest
Deal found 4/20$236
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 6/15:50 pm
PBI
-
MDW
1 stop7h 25m
Southwest
Wed 6/38:00 am
MDW
-
PBI
1 stop6h 15m
Southwest
Deal found 4/20$244
This Southwest deal was found by Cheapflights users on 4/20. 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.
Mon 5/185:50 pm
PBI
-
ORD
1 stop5h 05m
Southwest
Tue 5/191:35 pm
ORD
-
PBI
1 stop7h 15m
Southwest
Deal found 4/20$244
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/158:10 pm
PBI
-
ORD
1 stop23h 34m
Frontier
Thu 5/287:52 pm
ORD
-
PBI
1 stop22h 16m
Frontier
Deal found 4/18$247
This Kiwi.com deal was found by Cheapflights users on 4/20. 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.
Sat 5/163:13 pm
PBI
-
ORD
1 stop24h 26m
Multiple Airlines
Sun 5/247:52 pm
ORD
-
PBI
1 stop22h 16m
Multiple Airlines
Deal found 4/20$249
This Southwest deal was found by Cheapflights users on 4/22. 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 5/266:45 am
PBI
-
MDW
1 stop10h 30m
Southwest
Tue 6/28:00 am
MDW
-
PBI
1 stop6h 15m
Southwest
Deal found 4/22$250
This Southwest deal was found by Cheapflights users on 4/22. 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 5/266:00 pm
PBI
-
ORD
1 stop4h 55m
Southwest
Thu 5/282:40 pm
ORD
-
PBI
2 stops6h 15m
Southwest
Deal found 4/22$250
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 6/149:03 pm
PBI
-
MDW
1 stop23h 27m
Allegiant Air
Fri 6/198:20 pm
MDW
-
PBI
1 stop17h 55m
Allegiant Air
Deal found 4/21$252
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 5/88:10 pm
PBI
-
ORD
1 stop23h 34m
Multiple Airlines
Mon 5/114:05 pm
ORD
-
PBI
2 stops25h 46m
Multiple Airlines
Deal found 4/21$252
This Southwest deal was found by Cheapflights users on 4/19. 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.
Thu 5/286:20 am
PBI
-
MDW
2 stops6h 30m
Southwest
Tue 6/212:50 pm
MDW
-
PBI
2 stops7h 30m
Southwest
Deal found 4/19$255

Find flight deals from West Palm Beach to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from West Palm Beach (PBI) to Chicago (CHI). 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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$231
(Southwest)

One-way from

$122
(Southwest)

Popular in

November

Cheapest in

August

Average price

$318

Good round-trip deal

$296 or less

Good one-way deal

$247 or less
Provider with most accurate pricing for Palm Beach Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Palm Beach Intl-Chicago (CHI) flights.
Search Deals
From Palm Beach Intl to Chicago (CHI)
Search Deals
One-way flight from Palm Beach Intl to Chicago (CHI)
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Palm Beach Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Palm Beach Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from West Palm Beach to Chicago 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 April 23, 2026.
Use the filters below to find and compare flights from West Palm Beach to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Wed 5/20

6:00 pm-9:55 pm

1 stop4h 55m

Chicago O'Hare Intl

Wed 5/27

5:55 am-9:20 pm

2 stops14h 25m

$232

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 5/26

6:45 am-4:15 pm

1 stop10h 30m

Chicago Midway

Tue 6/2

12:50 pm-9:20 pm

2 stops7h 30m

$256

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 5/28

11:40 am-9:55 pm

2 stops11h 15m

Chicago O'Hare Intl

Tue 6/2

5:55 am-11:20 am

1 stop4h 25m

$256
Quickest round-trip

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 7/10

12:17 pm-2:51 pm

Nonstop3h 34m

Chicago O'Hare Intl

Mon 7/13

10:58 am-2:59 pm

Nonstop3h 01m

$289

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 7/31

12:17 pm-2:51 pm

Nonstop3h 34m

Chicago O'Hare Intl

Sun 8/2

7:10 am-11:11 am

Nonstop3h 01m

$289

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 5/26

4:14 pm-6:48 pm

Nonstop3h 34m

Chicago O'Hare Intl

Tue 6/2

10:58 am-2:59 pm

Nonstop3h 01m

$289

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 6/9

5:05 pm-11:14 pm

1 stop7h 09m

Chicago O'Hare Intl

Tue 6/30

10:58 am-2:59 pm

Nonstop3h 01m

$295

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Sat 6/20

5:05 pm-11:14 pm

1 stop7h 09m

Chicago O'Hare Intl

Fri 8/21

11:10 am-3:15 pm

Nonstop3h 05m

$295

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Wed 6/10

5:05 pm-11:14 pm

1 stop7h 09m

Chicago O'Hare Intl

Wed 6/17

7:30 am-3:56 pm

1 stop7h 26m

$304

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 6/2

5:05 pm-11:14 pm

1 stop7h 09m

Chicago O'Hare Intl

Wed 6/10

6:00 am-1:29 pm

1 stop6h 29m

$304

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 38 resultsSorted by cheapest first
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Compare providers for flights from West Palm Beach to Chicago

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 Chicago in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*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 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 flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from West Palm Beach-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on West Palm Beach-Chicago 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 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

How far ahead should I book a flight from West Palm Beach to Chicago?

The price you pay for your flight from West Palm Beach to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 81 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from West Palm Beach to Chicago?

Currently, February is the cheapest month in which you can book a flight from West Palm Beach to Chicago (average of $36). Flying from West Palm Beach to Chicago in June is currently the most expensive (average of $189). 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 CHI?

Find hourly flight availability from West Palm Beach to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.

Unlike in the evening, when flights are generally more expensive, you can save up to 24% on flights from West Palm Beach to Chicago by exploring options for tickets at noon.

Weekly flight availability from West Palm Beach to Chicago

Explore weekly flight availability from West Palm Beach to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 23, 2026.

The most flights from PBI to CHI are scheduled on a Thursday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).

How much does it cost to fly round-trip from West Palm Beach to Chicago?

The best insider tips for West Palm Beach to Chicago flights

AI-powered summary based on content written by travel experts. AI can make mistakes.
Cheapflights partnered with top experts to bring you the best recommendations for your West Palm Beach to Chicago trip
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and PBI

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 23, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from West Palm Beach to Chicago by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Delta
7.9
Good
8,438 reviews
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
United Airlines
7.4
Good
9,635 reviews
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
American Airlines
7.1
Good
11,659 reviews
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Spirit Airlines
6.3
Okay
8,633 reviews
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.
Frontier
5.7
Fair
2,981 reviews
Delta
7.9
Good
8,438 reviews

Entertainment

7.8

Comfort

7.9

Food

7.2

Crew

8.5

Overall

7.9

Boarding

8.1

Reviews

1 / 20
6.0
Good

pilar,May 2025

RSW - ATL

The stewardess was not very nice because I requested two glasses of water. She didn’t even offer the snacks to me. She seemed angry and I felt very bad about her reaction. Also, the flight was full and you could not move. The airline should provide seats for obese people in consideration to the rest pf the passengers.

Related info for your journey

Find useful and relevant information for your journey from West Palm Beach to Chicago. 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?

    Palm Beach Intl (PBI) is the airport you will fly out of if you book a flight from West Palm Beach to Chicago. You should not have trouble finding flights to Chicago from Palm Beach Intl; the airport handles an average of 7 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 5 airlines have flights from the West Palm Beach airport to Chicago. It is only a 3.1 mi journey to Palm Beach Intl (PBI) from West Palm Beach’s city center.

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

    A quick flight from West Palm Beach to Chicago can take about 3h 34m. Southwest provides one of the quickest options available for as low as $289. There are 1145 mi between West Palm Beach and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines flying from West Palm Beach to Chicago round-trip?

    Cheapflights users have booked flights from West Palm Beach to Chicago round-trip from $107. Other airlines that can offer you cheap pricing are Southwest, from $149, and Delta, from $209. You may be able to fly from West Palm Beach to Chicago for 64% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from West Palm Beach to Chicago one-way?

    The cheapest airlines for a one-way flight from West Palm Beach to Chicago are Frontier ($94), Southwest ($103), and Delta ($125).

  • What are the most reliable airlines from West Palm Beach to Chicago?

    No one likes to see their flight delayed. When booking a flight from West Palm Beach to Chicago consider choosing Air New Zealand (72%), Qatar Airways (71%) or United Airlines (70%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from West Palm Beach to Chicago?

    The cheapest flight price from West Palm Beach to Chicago is $149. On average you can expect to pay $674. The most popular route, (Palm Beach Intl - Chicago O'Hare Intl), can usually be booked for $289.

  • Can I find deals for flights from West Palm Beach to Chicago that include hotel bookings?

    Yes. In addition to deals on West Palm Beach to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from West Palm Beach to Chicago?

    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 Chicago.

  • Can I find deals for business class flights from West Palm Beach to Chicago?

    Yes. Cheapflights offers flight deals from West Palm Beach to Chicago 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?

    Currently, February is the cheapest month in which you can book a flight from West Palm Beach to Chicago (average of $36). Flying from West Palm Beach to Chicago in June is currently the most expensive (average of $189). 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?

Book flights to Chicago if you plan to visit one of these locations
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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Alternative routes for West Palm Beach to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from West Palm Beach to Chicago

Discover the top 5 airlines that operate flights from West Palm Beach to Chicago. 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 April 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$107Average$176FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$370FlexibilityNo cancel feeOn-time63%
DeltaCheapest$209Average$323FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$210Average$301FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$229Average$309FlexibilityNo cancel feeOn-time69%

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