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$125+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Thursday 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 June 12, 2025.

Round-trip from

$229
(American Airlines)

One-way from

$125
(Delta)

Popular in

September

Cheapest in

February

Average price

$311

Good round-trip deal

$269 or less

Good one-way deal

$196 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. 3% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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.
Thu 7/176:41 pmPBI - ORD
Nonstop3h 17mAmerican Airlines
Wed 7/238:22 amORD - PBI
Nonstop2h 57mAmerican Airlines
Deal found 6/11$229
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/76:36 amPBI - ORD
1 stop6h 34mJetBlue
Sun 9/146:45 amORD - PBI
1 stop8h 23mJetBlue
Deal found 6/11$243
This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/127:13 pmPBI - MDW
1 stop5h 12mFrontier
Sun 9/147:23 pmMDW - PBI
1 stop21h 55mFrontier
Deal found 6/11$247
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/207:15 pmPBI - MDW
1 stop5h 40mSouthwest
Tue 7/227:15 amMDW - PBI
1 stop7h 55mSouthwest
Deal found 6/10$249
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/157:20 amPBI - ORD
1 stop5h 30mSouthwest
Wed 7/161:50 pmORD - PBI
1 stop6h 40mSouthwest
Deal found 6/10$249
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/112:45 pmPBI - ORD
1 stop5h 04mDelta
Tue 7/89:25 amORD - PBI
1 stop8h 32mDelta
Deal found 6/11$250
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/304:59 pmPBI - MDW
1 stop5h 13mDelta
Mon 9/86:00 amMDW - PBI
1 stop6h 32mDelta
Deal found 6/10$259
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/311:36 amPBI - MDW
1 stop25h 45mAllegiant Air
Wed 8/64:27 pmMDW - PBI
2 stops26h 07mAllegiant Air
Deal found 6/11$263
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/276:46 pmPBI - ORD
1 stop6h 28mFrontier
Mon 6/305:01 amORD - PBI
1 stop11h 50mFrontier
Deal found 6/10$270
This Trip.com deal was found by Cheapflights users on 6/11. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/276:46 pmPBI - ORD
1 stop6h 28mMultiple Airlines
Mon 6/3010:43 amORD - PBI
1 stop6h 08mMultiple Airlines
Deal found 6/11$305
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/192:57 pmPBI - ORD
1 stop9h 28mUnited Airlines
Mon 9/226:10 pmORD - PBI
2 stops16h 02mUnited Airlines
Deal found 6/10$367

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 June 12, 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

Thu 7/17

6:41 pm-8:58 pm

Nonstop3h 17m

Chicago O'Hare Intl

Wed 7/23

8:22 am-12:19 pm

Nonstop2h 57m

$229

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Sun 9/7

6:36 am-12:10 pm

1 stop6h 34m

Chicago O'Hare Intl

Sun 9/14

6:45 am-4:08 pm

1 stop8h 23m

$243

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 9/12

7:13 pm-11:25 pm

1 stop5h 12m

Chicago Midway

Sun 9/14

7:23 pm-6:18 pm

1 stop21h 55m

$247

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 7/20

7:15 pm-11:55 pm

1 stop5h 40m

Chicago Midway

Tue 7/22

7:15 am-4:10 pm

1 stop7h 55m

$249

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 7/15

7:20 am-11:50 am

1 stop5h 30m

Chicago O'Hare Intl

Wed 7/16

1:50 pm-9:30 pm

1 stop6h 40m

$249

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 7/1

6:27 pm-11:59 pm

1 stop6h 32m

Chicago O'Hare Intl

Tue 7/8

3:29 pm-11:48 pm

1 stop7h 19m

$250

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 8/3

11:36 am-12:21 pm

1 stop25h 45m

Chicago Midway

Wed 8/6

4:27 pm-7:34 pm

2 stops26h 07m

$263

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sat 6/28

6:00 am-9:41 am

1 stop4h 41m

Chicago Midway

Sat 7/5

6:00 am-11:40 am

1 stop4h 40m

$264

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 6/27

6:46 pm-12:14 am

1 stop6h 28m

Chicago O'Hare Intl

Mon 6/30

5:01 am-5:51 pm

1 stop11h 50m

$270

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 6/27

6:46 pm-12:14 am

1 stop6h 28m

Chicago O'Hare Intl

Mon 6/30

10:43 am-5:51 pm

1 stop6h 08m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 23 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 June 9, 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 June 12, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 68% 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 June 12, 2025.

The most flights from PBI to CHI are scheduled on a Thursday (6 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
See what other customers who have flown with Southwest, Delta and United Airlines from West Palm Beach to Chicago 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
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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.
Allegiant Air
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Crew

8.6

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 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 $229. Other airlines that can offer you cheap pricing are JetBlue, from $243, and Frontier, from $247. You may be able to fly from West Palm Beach to Chicago for 22% 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 Delta ($125), Southwest ($130), and JetBlue ($132).

  • 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 (86%), Qatar Airways (84%) or United Airlines (82%) 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 $119. On average you can expect to pay $770. 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 West Palm Beach?

Book flights to West Palm Beach if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$129FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$76Average$127FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$198Average$412FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$201Average$303FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$204Average$334FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$341FlexibilityNo cancel feeOn-timeN/A

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