Southwest® flights from West Palm Beach to Chicago (O'Hare) from $135

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Low fares from West Palm Beach to Chicago (O'Hare)

$

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 05/13/2026

One-way

Basic

From
$135
Seen: 10 hrs ago

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 04/08/2026

One-way

Basic

From
$135
Seen: 7 hrs ago

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 04/22/2026

One-way

Basic

From
$135
Seen: 1 hour ago

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 04/14/2026

One-way

Basic

From
$135
Seen: 21 hrs ago

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 04/15/2026

One-way

Basic

From
$135
Seen: 11 hrs ago

West Palm Beach (PBI)to

Chicago (Midway) (MDW)
Depart: 04/21/2026

One-way

Basic

From
$135
Seen: 11 hrs ago

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Explore flights from West Palm Beach to Chicago (O'Hare)

Mar 2026
From$170*
Seen: 10 hrs ago
One Way/Basic
Apr 2026
From$135*
Seen: 7 hrs ago
One Way/Basic
May 2026
From$135*
Seen: 10 hrs ago
One Way/Basic
$135
$299
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    • Range$135-$299

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Palm Beach International Airport
    Arriving at:
    O'Hare International Airport
    Distance:
    1144 miles

    Route Information

    47† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 47 weekly flights from West Palm Beach to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly West Palm Beach to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from West Palm Beach to Chicago (O'Hare)—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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