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$98+ 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — CHI
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheapflights Tip: The best prices from Palm Beach Intl to Chicago are usually found in February or August, booked 54 days in advance, depart on a Friday or Wednesday and return on a Wednesday

Cheap 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 August 13, 2025.

Round-trip from

$217
(JetBlue)

One-way from

$98
(Priceline)

Popular in

November

Cheapest in

February

Average price

$247

Good round-trip deal

$234 or less

Good one-way deal

$166 or less
From Palm Beach Intl to Chicago (CHI)
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One-way flight from Palm Beach Intl to Chicago (CHI)
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Highest demand for flights based on searches. 6% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from Palm Beach Intl to Chicago (CHI).
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Price to beat on a one-way flight from Palm Beach Intl to Chicago (CHI).
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Find 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 August 13, 2025.

This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/186:48 pmPBI - MDW
1 stop15h 14mFrontier
Mon 8/252:05 pmMDW - PBI
1 stop23h 39mFrontier
Deal found 8/11$216
This JetBlue deal was found by Cheapflights users on 8/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/72:00 pmPBI - ORD
1 stop7h 52mJetBlue
Sun 11/96:44 amORD - PBI
1 stop8h 54mJetBlue
Deal found 8/12$217
This Frontier deal was found by Cheapflights users on 8/11. 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 10/169:40 amPBI - ORD
1 stop9h 00mFrontier
Thu 10/235:05 amORD - PBI
1 stop6h 09mFrontier
Deal found 8/11$218
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 9/104:59 pmPBI - MDW
1 stop5h 27mDelta
Wed 9/1710:35 amMDW - PBI
1 stop4h 19mDelta
Deal found 8/12$219
This Delta deal was found by Cheapflights users on 8/12. 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.
Tue 9/911:05 amPBI - ORD
1 stop7h 57mDelta
Tue 9/166:00 amORD - PBI
1 stop7h 33mDelta
Deal found 8/12$219
This Priceline deal was found by Cheapflights users on 8/11. 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 8/227:10 pmPBI - MDW
1 stop5h 17mFrontier
Mon 8/2510:58 amMDW - PBI
1 stop6h 27mFrontier
Deal found 8/11$221
This Trip.com deal was found by Cheapflights users on 8/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/26:00 amPBI - ORD
1 stop10h 32mJetBlue
Tue 9/91:36 pmORD - PBI
1 stop6h 58mJetBlue
Deal found 8/10$221
This Priceline deal was found by Cheapflights users on 8/12. 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 10/317:13 pmPBI - ORD
1 stop5h 46mFrontier
Mon 11/310:10 amORD - PBI
1 stop7h 08mFrontier
Deal found 8/12$222
This Southwest deal was found by Cheapflights users on 8/11. 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 9/167:30 amPBI - MDW
2 stops6h 55mSouthwest
Wed 9/177:25 amMDW - PBI
1 stop6h 00mSouthwest
Deal found 8/11$224
This FlightHub deal was found by Cheapflights users on 8/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/121:12 pmPBI - ORD
1 stop23h 15mFrontier
Mon 9/155:10 amORD - PBI
1 stop6h 07mFrontier
Deal found 8/11$226
This United Airlines deal was found by Cheapflights users on 8/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/264:10 pmPBI - ORD
Nonstop3h 23mUnited Airlines
Sun 9/2810:58 amORD - PBI
Nonstop3h 10mUnited Airlines
Deal found 8/11$229
This American Airlines deal was found by Cheapflights users on 8/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/208:00 amPBI - ORD
Nonstop3h 12mAmerican Airlines
Sat 9/2712:00 pmORD - PBI
Nonstop2h 58mAmerican Airlines
Deal found 8/11$231

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 August 13, 2025.
Use the filters below to find and compare flights from West Palm Beach to Chicago that are best for you.

Fly from

West Palm Beach

Fly to

Chicago

Route

Depart

Return

Price

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 9/5

11:15 am-5:54 pm

1 stop7h 39m

Chicago O'Hare Intl

Sun 9/7

6:45 am-4:15 pm

1 stop8h 30m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 9/19

6:35 am-12:10 pm

1 stop6h 35m

Chicago O'Hare Intl

Mon 9/22

1:35 pm-10:00 pm

1 stop7h 25m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Mon 9/29

6:35 am-12:10 pm

1 stop6h 35m

Chicago O'Hare Intl

Thu 10/2

1:35 pm-10:00 pm

1 stop7h 25m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 11/7

2:00 pm-8:52 pm

1 stop7h 52m

Chicago O'Hare Intl

Sun 11/9

6:44 am-4:38 pm

1 stop8h 54m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 10/30

1:41 pm-8:52 pm

1 stop8h 11m

Chicago O'Hare Intl

Sun 11/2

5:44 am-3:38 pm

1 stop8h 54m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Mon 9/29

6:35 am-12:10 pm

1 stop6h 35m

Chicago O'Hare Intl

Fri 10/3

1:36 pm-10:00 pm

1 stop7h 24m

$217

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 9/10

4:59 pm-9:26 pm

1 stop5h 27m

Chicago Midway

Wed 9/17

6:00 am-11:38 am

1 stop4h 38m

$219

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 9/16

11:30 am-4:25 pm

1 stop5h 55m

Chicago Midway

Wed 9/17

11:45 am-6:50 pm

1 stop6h 05m

$219

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 9/16

8:30 am-11:48 am

1 stop4h 18m

Chicago Midway

Tue 9/23

10:35 am-5:20 pm

1 stop5h 45m

$219

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 9/2

6:40 am-11:50 am

1 stop6h 10m

Chicago Midway

Tue 9/9

8:35 am-3:30 pm

1 stop5h 55m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 36 results
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The best insider tips for West Palm Beach to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your West Palm Beach to Chicago trip
Airports
PBI

PBI's easy-to-navigate terminal features a landside shopping and dining area with natural light and workstations, perfect for business travelers.

Read more about PBIby Ramsey Qubein
ORD

For a quick city transfer, take the 'L' train from ORD to downtown Chicago, avoiding traffic delays.

Read more about ORDby Ramsey Qubein
Our travel experts
Ramsey Qubein

Ramsey Qubein

Expert on ORD and PBI

Ramsey Qubein

Ramsey Qubein

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

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?

Use this chart to determine the optimal time to book a round-trip flight from West Palm Beach to Chicago. Price data was last updated on August 8, 2025.

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 54 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, August is the cheapest month in which you can book a flight from West Palm Beach to Chicago (average of $245). Flying from West Palm Beach to Chicago in March is currently the most expensive (average of $321). 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 August 13, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 67% on flights from West Palm Beach to Chicago by exploring options for tickets in the evening.

What is the cheapest day to fly from West Palm Beach to Chicago?

Use this chart to determine the cheapest time to fly round-trip from West Palm Beach to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their West Palm Beach to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 August 13, 2025.

The most flights from PBI to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).

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 August 13, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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
8,920 reviews
Delta
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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
8,048 reviews
Delta
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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
5.8
Fair
3,221 reviews
Delta
8.0
Very good
7,979 reviews

Boarding

8.2

Entertainment

7.9

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

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 4 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 6 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.

  • 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 $217. Other airlines that can offer you cheap pricing are Frontier, from $218, and Delta, from $219. You may be able to fly from West Palm Beach to Chicago for 25% less than the average price by searching for these airlines.

  • 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 Qatar Airways (79%), American Airlines (73%) or Alaska Airlines (73%) 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 $98. On average you can expect to pay $291. The most popular route, (Palm Beach Intl - Chicago O'Hare Intl), can usually be booked for $217.

  • 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, August is the cheapest month in which you can book a flight from West Palm Beach to Chicago (average of $245). Flying from West Palm Beach to Chicago in March is currently the most expensive (average of $321). 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
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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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 6 airlines flying from West Palm Beach to Chicago

Discover the top 6 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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$131FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$82Average$154FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$149Average$288FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$187Average$293FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$335FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$344FlexibilityNo cancel feeOn-timeN/A

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