'How To Get The Best Deal' Guides

Sunday, September 25th 2022

"I'm a travel junkie who's hooked on deals from YYC." - Chris Myden

Tagged Pages Archive | Illinois

The 'United or AA has dropped their last minute flights to Chicago' thread

American Airlines just dropped another one of those cheap flights to Chicago. Try July 2 to 4 on AA.com - $335 roundtrip after tax, direct each way.

Next cheapest is Delta at $691. Next cheapest non-stop is Air Canada at $829.

United and American Airlines both occasionally drop the price of their last minute flights from Calgary to Chicago.

They usually drop them to around $330 roundtrip after tax, which is nearly 50% cheaper than it usually costs to get to Chicago, last minute or not.

The drop usually occurs the 'week of' departure, and it's almost always the Saturday to Monday/Tuesday flights.

They happen enough now that I probably won't make a blog post every time they do it, it gets a little old. But if you want to keep up with the drops, keep an eye on the following thread on the forums:


If you click on 'Watch Topic' at the top of the forum thread you can be notified when the thread is updated.

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Last minute May long weekend idea? There's a flight to Chicago for $334 after tax.

If anyone's looking for a last minute May long weekend idea, there's a flight on American Airlines to Chicago for $334 roundtrip after tax.

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Another cheap last minuter to Chicago - $341 roundtrip after tax

UPDATE @ 8:05 AM - This AA price has now sold out, but interestingly enough, Delta has matched it, but into Chicago's other airport (MDW).

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Last minute flight from Calgary to Chicago - $336 roundtrip after tax - direct

If you've ever tried to fly to Chicago from Calgary, you know it's an expensive city to get to. You're usually lucky if you can find something for around $550-$650 roundtrip after tax. And around $700ish for anything direct.

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Calgary to Chicago - $400 roundtrip after tax

Chicago doesn't go on sale all that often, it usually hovers around $550-$700 roundtrip after tax.

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