Chicago is known for brutal winters. After digging their cars out of the snow, Chicagoans are not going to let someone else waltz in and take the spot they just worked so hard to clear. They claim it in a uniquely Chicago way: They stick some chairs in the snow and call dibs.
In January 2026, Southwest announced its largest partnership in history with the beloved Chicago Cubs in the most Chicago way possible…
By calling dibs.
Leaning into the city’s dibs tradition, Southwest brought Opening Day energy to January by planting an oversized airline seat in front of the marquee, officially calling dibs as the new airline partner of the Chicago Cubs. From 11am–3pm, fans entered through a jet bridge tunnel and were welcomed with Southwest’s signature in-flight hospitality, including hot cocoa topped with the coveted heart marshmallow. Guests called dibs on exclusive swag, snapped photos in the oversized seat, enjoyed free ice skating, and met Cubs legends like Pete Crow-Armstrong and Pat Hughes. The result was pure joy at the Friendly Confines, setting the tone for what’s ahead.
In true Chicago fashion, we faced high winds, snow, and rain, but Chicagoans still showed up. Over the course
of 4 hours, we distributed 1,040 premiums, captured 648 sweepstakes entries, and covered the cost of skating
for 134 guests.
of 4 hours, we distributed 1,040 premiums, captured 648 sweepstakes entries, and covered the cost of skating
for 134 guests.
Across the street, Swift Tavern Swift became a welcoming VIP destination where invited guests could relax, connect, and enjoy food and drinks. A standout feature was the Alice & Wonder hat and patch bar, where attendees selected a hat and custom patches, including the Southwest heart. The Cubs locker room photo op with hanging Pete Crow-Armstrong jerseys also drove strong engagement, offering an authentic, immersive moment. Surprise appearances by Pete Crow-Armstrong and Clark the Cub capped off the evening with excitement and memorable photo moments.
Sports Business Journal | Cubs ink Southwest Airlines as sponsor, assets include branding at Wrigley Field
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Southwest Newsroom | Southwest Airlines Celebrated New Legacy Partnership with the Chicago Cubs with Fan Experience at Wrigley Field