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Hey awardtrail readers! Dreaming of deep-dish pizza or catching a Cubs game? There's a flash sale on flights to and from Chicago, with prices starting at just $231 for a round trip.
To snag this deal, you'll want to head over to ITA Matrix Airfare Search. It's a nifty tool that lets you find the lowest fares (just Google "ITA Matrix" if you're not familiar). Once you find the dates that work for you, book directly with the airline – that way, you're protected if there are any flight changes or cancellations.
Why should you care? Well, duh, cheap flights! This is a fantastic opportunity to explore Chicago without breaking the bank. Plus, if you're strategic about your airline and credit card choices, you could rack up some serious miles and points on these flights. Happy travels!
Why This Matters for Your Strategy
News in the points-and-miles world moves fast, and promotional changes often have a short window. If this announcement affects a card or program you hold, log into your awardtrail dashboard to check your current benefit usage, bonus progress, and whether a transfer or redemption makes sense right now — before terms change.
As a general rule: transfer points only when you have a specific redemption in mind — transfers are almost always one-way and non-reversible. If you're unsure of the value, check our redemption guides before acting.
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October 8, 2026, 9:16 PM
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