Chicago

$75+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — CHI
Jul 13 — Jul 201
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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 July 8, 2025.

Round-trip from

$208
(Southwest)

One-way from

$75
(Southwest)

Popular in

September

Cheapest in

February

Average price

$309

Good round-trip deal

$229 or less

Good one-way deal

$241 or less
From Palm Beach Intl to Chicago (CHI)
One-way flight from Palm Beach Intl to Chicago (CHI)
Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Palm Beach Intl to Chicago (CHI).
Price to beat on a one-way flight from Palm Beach Intl to Chicago (CHI).

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 July 8, 2025.

This Southwest deal was found by Cheapflights users on 7/8. 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 9/87:15 amPBI - ORD
2 stops11h 40mSouthwest
Thu 9/116:00 amORD - PBI
2 stops10h 45mSouthwest
Deal found 7/8$205
This Southwest deal was found by Cheapflights users on 7/7. 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.
Fri 8/157:15 amPBI - MDW
2 stops7h 15mSouthwest
Sun 8/1710:05 amMDW - PBI
2 stops9h 45mSouthwest
Deal found 7/7$208
This American Airlines deal was found by Cheapflights users on 7/8. 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.
Wed 7/231:09 pmPBI - ORD
Nonstop3h 16mAmerican Airlines
Tue 8/51:44 pmORD - PBI
Nonstop3h 00mAmerican Airlines
Deal found 7/8$208
This United Airlines deal was found by Cheapflights users on 7/8. 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.
Sat 12/139:15 amPBI - ORD
Nonstop3h 22mUnited Airlines
Sun 1/411:10 amORD - PBI
Nonstop3h 05mUnited Airlines
Deal found 7/8$213
This Delta deal was found by Cheapflights users on 7/8. 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 7/296:00 amPBI - MDW
1 stop4h 45mDelta
Wed 8/2012:43 pmMDW - PBI
1 stop4h 43mDelta
Deal found 7/8$217
This Delta deal was found by Cheapflights users on 7/7. 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.
Thu 8/146:29 pmPBI - ORD
1 stop6h 27mDelta
Mon 8/187:05 amORD - PBI
1 stop5h 27mDelta
Deal found 7/7$217
This JetBlue deal was found by Cheapflights users on 7/7. 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.
Sat 9/610:48 amPBI - ORD
1 stop8h 36mJetBlue
Sat 10/49:42 amORD - PBI
1 stop8h 01mJetBlue
Deal found 7/7$253
This Priceline deal was found by Cheapflights users on 7/8. 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 10/107:13 pmPBI - ORD
1 stop5h 57mFrontier
Mon 10/1310:11 amORD - PBI
1 stop7h 07mFrontier
Deal found 7/8$260
This Frontier deal was found by Cheapflights users on 7/7. 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.
Fri 8/227:10 pmPBI - MDW
1 stop5h 17mFrontier
Mon 8/256:15 amMDW - PBI
1 stop11h 10mFrontier
Deal found 7/7$296

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 July 8, 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 - MDW

PBIMDW

Palm Beach Intl

Fri 8/15

7:15 am-1:30 pm

2 stops7h 15m

Chicago Midway

Sun 8/17

10:05 am-8:50 pm

2 stops9h 45m

$208

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 7/29

1:09 pm-3:25 pm

Nonstop3h 16m

Chicago O'Hare Intl

Wed 8/20

8:27 am-12:25 pm

Nonstop2h 58m

$208

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 8/28

7:15 am-5:55 pm

2 stops11h 40m

Chicago O'Hare Intl

Fri 8/29

1:50 pm-9:15 pm

1 stop6h 25m

$216

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 7/29

6:00 am-9:45 am

1 stop4h 45m

Chicago Midway

Wed 8/20

12:43 pm-6:26 pm

1 stop4h 43m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 8/14

6:29 pm-11:56 pm

1 stop6h 27m

Chicago O'Hare Intl

Mon 8/18

7:05 am-1:32 pm

1 stop5h 27m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Sat 9/6

10:48 am-6:24 pm

1 stop8h 36m

Chicago O'Hare Intl

Sat 10/4

9:42 am-6:43 pm

1 stop8h 01m

$253

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 11/21

4:09 pm-6:39 pm

Nonstop3h 30m

Chicago O'Hare Intl

Mon 11/24

7:15 am-2:36 pm

1 stop6h 21m

$258

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 8/22

7:10 pm-11:27 pm

1 stop5h 17m

Chicago Midway

Mon 8/25

6:15 am-6:25 pm

1 stop11h 10m

$296

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Tue 8/19

6:40 am-11:50 am

1 stop6h 10m

$75

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 8/21

12:40 pm-4:25 pm

1 stop4h 45m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/6

Showing 1-10 of 18 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 27, 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 July 8, 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 July 8, 2025.

The most flights from PBI to CHI are scheduled on a Monday (5 on average). You will have fewer flight options on Saturday, 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 July 8, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and JetBlue 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.

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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.

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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.
8.0
Very good

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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.

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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.

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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.

Boarding

8.2

Comfort

8.0

Overall

8.0

Food

7.0

Entertainment

7.6

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 $208. Other airlines that can offer you cheap pricing are American Airlines, from $208, and Delta, from $217. You may be able to fly from West Palm Beach to Chicago for 29% 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 Southwest ($75), Frontier ($76), and American Airlines ($94).

  • 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 (87%), Alaska Airlines (75%) 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 $109. On average you can expect to pay $492. The most popular route, (Palm Beach Intl - Chicago O'Hare Intl), can usually be booked for $150.

  • 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
Hammond
Benton Harbor
Porter
Valparaiso
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.

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 July 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$131FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$82Average$133FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$192Average$298FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$288FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$204Average$338FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$339FlexibilityNo cancel feeOn-timeN/A

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