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$100+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
PBI — CHI
Apr 20 — Apr 271
Sun 4/20
Sun 4/27
1 adult, Economy
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Find cheap flights from West Palm Beach to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

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3. Compare prices and book

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Cheapflights Tip: The best prices from Palm Beach Intl to Chicago are usually found in February or May, 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 April 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$186
(American Airlines)

One-way from

$100
(Southwest)

Popular in

September

Cheapest in

February

Average price

$299

Good round-trip deal

$229 or less

Good one-way deal

$150 or less
Provider with most accurate pricing for Palm Beach Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Palm Beach Intl-Chicago (CHI) flights.
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From Palm Beach Intl to Chicago (CHI)
Search Deals
One-way flight from Palm Beach Intl to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
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

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 April 15, 2025.

This American Airlines deal was found by Cheapflights users on 4/15. 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 5/285:11 pmPBI - ORD
Nonstop3h 22mAmerican Airlines
Wed 6/412:14 pmORD - PBI
Nonstop3h 01mAmerican Airlines
Deal found 4/15$186
This Southwest deal was found by Cheapflights users on 4/14. 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 5/285:30 pmPBI - MDW
1 stop5h 20mSouthwest
Wed 6/46:20 amMDW - PBI
1 stop7h 50mSouthwest
Deal found 4/14$204
This Delta deal was found by Cheapflights users on 4/14. 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 5/144:51 pmPBI - MDW
1 stop5h 37mDelta
Wed 5/216:00 amMDW - PBI
1 stop4h 53mDelta
Deal found 4/14$217
This Delta deal was found by Cheapflights users on 4/13. 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 5/206:00 amPBI - ORD
1 stop5h 03mDelta
Wed 5/289:25 amORD - PBI
1 stop8h 06mDelta
Deal found 4/13$217
This United Airlines deal was found by Cheapflights users on 4/14. 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.
Tue 5/134:11 pmPBI - ORD
Nonstop3h 29mUnited Airlines
Wed 5/1410:49 amORD - PBI
Nonstop3h 12mUnited Airlines
Deal found 4/14$231
This CheapOair deal was found by Cheapflights users on 4/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/1510:12 amPBI - MDW
1 stop10h 39mFrontier
Sun 4/208:00 amMDW - PBI
1 stop12h 48mFrontier
Deal found 4/15$261
This Cheapflightsfares deal was found by Cheapflights users on 4/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1811:49 amPBI - ORD
Nonstop3h 28mFrontier
Mon 4/216:30 amORD - PBI
Nonstop3h 14mFrontier
Deal found 4/15$292
This Southwest deal was found by Cheapflights users on 4/14. 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.
Sat 5/316:05 amPBI - ORD
1 stop7h 40mSouthwest
Mon 6/27:30 amORD - PBI
2 stops9h 00mSouthwest
Deal found 4/14$308
This JetBlue deal was found by Cheapflights users on 4/14. 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.
Wed 4/306:00 amPBI - ORD
1 stop7h 13mJetBlue
Sat 5/36:20 amORD - PBI
1 stop10h 06mJetBlue
Deal found 4/14$313
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Thu 5/159:46 amPBI - ORD
3 stops14h 43mMultiple Airlines
Sun 5/184:26 pmORD - PBI
1 stop16h 02mMultiple Airlines
Deal found 4/14$368
This Mytrip deal was found by Cheapflights users on 4/14. 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.
Tue 5/610:42 amPBI - ORD
3 stops37h 22mSpirit Airlines
Thu 5/810:00 amORD - PBI
3 stops24h 23mSpirit Airlines
Deal found 4/14$386
This Mytrip deal was found by Cheapflights users on 4/14. 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 6/2211:39 amPBI - MDW
1 stop23h 05mAllegiant Air
Thu 6/2611:45 amMDW - PBI
2 stops22h 52mAllegiant Air
Deal found 4/14$403

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 15, 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

Wed 5/28

11:38 am-2:00 pm

Nonstop3h 22m

Chicago O'Hare Intl

Wed 6/4

12:14 pm-4:15 pm

Nonstop3h 01m

$188

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 5/28

5:30 pm-9:50 pm

1 stop5h 20m

Chicago Midway

Wed 6/4

6:20 am-3:10 pm

1 stop7h 50m

$204

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Wed 5/14

4:51 pm-9:28 pm

1 stop5h 37m

Chicago Midway

Wed 5/21

6:00 am-11:53 am

1 stop4h 53m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Tue 5/6

6:14 am-3:04 pm

1 stop9h 50m

Chicago O'Hare Intl

Tue 5/13

6:15 am-5:26 pm

1 stop10h 11m

$217

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Sat 5/10

4:03 pm-6:32 pm

Nonstop3h 29m

Chicago O'Hare Intl

Tue 5/13

10:49 am-3:01 pm

Nonstop3h 12m

$219

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Wed 5/14

3:10 pm-9:20 pm

1 stop7h 10m

Chicago O'Hare Intl

Wed 5/21

9:39 am-3:46 pm

1 stop5h 07m

$223

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 6/5

11:13 am-6:11 pm

1 stop7h 58m

Chicago O'Hare Intl

Sun 6/8

6:26 pm-11:48 am

1 stop16h 22m

$272

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Thu 6/5

11:13 am-11:29 pm

2 stops13h 16m

Chicago O'Hare Intl

Sun 6/8

6:26 pm-11:48 am

1 stop16h 22m

$301

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Sat 5/31

6:05 am-12:45 pm

1 stop7h 40m

Chicago O'Hare Intl

Mon 6/2

7:30 am-5:30 pm

2 stops9h 00m

$308

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 7/4

6:46 pm-11:18 pm

1 stop5h 32m

Chicago Midway

Mon 7/7

6:20 am-5:51 pm

1 stop10h 31m

$342

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/13

Showing 1-10 of 25 results
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2
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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*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust Score*3 stars

*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 eDreams the most. eDreams 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?

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 April 11, 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 April 15, 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 April 15, 2025.

The most flights from PBI to CHI are scheduled on a Monday (11 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (3 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 April 15, 2025.
See what other customers who have flown with Southwest, Delta and Avelo 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
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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
4,279 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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
7,918 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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.
Avelo Airlines
7.5
Good
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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
8,658 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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
2,927 reviews
Southwest
8.0
Very good
4,279 reviews

Crew

8.6

Entertainment

7.6

Food

7.1

Boarding

8.2

Comfort

8.0

Overall

8.0

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 8 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 $186. Other airlines that can offer you cheap pricing are Southwest, from $204, and Delta, from $217. You may be able to fly from West Palm Beach to Chicago for 34% 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 ($100), United Airlines ($116), and Frontier ($118).

  • 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 Emirates (92%), Air New Zealand (76%) 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 $89. On average you can expect to pay $473. 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
Hammond
Benton Harbor
Porter
Lansing
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 April 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$48Average$127FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$122FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$190Average$303FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$198Average$288FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$204Average$334FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$344FlexibilityNo cancel feeOn-timeN/A

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