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Note about this deal
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It's official: Southwest's bags fly free policy is going the way of the dodo on May 28th. So for all of you bag checkers out there, this is your final opportunity to take advantage and book a cheap domestic getaway, bags included.
In our never ending quest to save you as much dough as possible, we unearthed these prices to Chicago for you. If you're a bag checker and the Windy City is on your 2025 radar, we'd recommend locking in a deal now: you'll be saving a minimum of $70 per person on bags roundtrip.
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