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Heads up, deal hunters! The Flight Deal has spotted some seriously cheap flights to and from Chicago. We're talking prices as low as $161 for a round trip. This is big news because Chicago is a fantastic city to visit, whether you're into architecture, deep-dish pizza, or catching a Cubs game.
The key to snagging this deal is using the Matrix Airfare Search by ITA Software (a tool some travel gurus use) to find the dates with the lowest prices. Once you've found the cheap dates on Matrix Airfare Search, you'll then use those dates when booking on the airline's website. This could be a great opportunity to explore the Windy City on a budget or visit friends and family without breaking the bank. So get searching and 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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