Southwest Airlines Runway to Wrigley Sweepstakes

Posted July 13, 2026

NEW

Southwest Airlines Runway to Wrigley Sweepstakes

Win a trip for 2 to attend a Chicago Cubs home game in Chicago, IL!

Trip includes hotel, game tickets, a jersey signed by Pete Crow-Armstrong, a signed baseball, a baseball card, and 50,000 Southwest Airlines Rapid Rewards for airfare!

To be eligible, you must be a Southwest Airlines Rapid Rewards member – it’s free.

Have your membership number handy because you’ll need it for the entry form.

If you’re new to Rapid Rewards, you can sign up here.

Click Here To Enter

Next Sweep »

Entry Frequency:
Single Entry

Eligibility:
Open to residents of the fifty (50) United States and DC (excludes RI), ages 18 and older.

Start Date:
July 8, 2026

End Date:
August 5, 2026

Official Rules:
View Rules Page

Prizes:

One (1) Prize Winner will receive:

two (2) tickets for the winner and one (1) guest to a 2026 Chicago Cubs regular-season home game
one (1) Wrigley Field scoreboard viewing experience
50,000 Southwest Airlines Rapid Rewards bonus points
one (1) night hotel stay
one (1) Pete Crow-Armstrong autographed jersey
one (1) Pete Crow-Armstrong autographed baseball
one (1) Pete Crow-Armstrong autographed baseball card
one (1) Chicago Cubs x Southwest hat and pin

(ARV: $3,052.41)

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Southwest Airlines Runway to Wrigley Sweepstakes

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