'How To Get The Best Deal' Guides

Friday, July 19th 2024

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


Tagged Pages Archive | Chicago

2013
20
March
Calgary to New York City | $354 roundtrip after taxes

New York City

United Airlines looks to have just dropped many of their airfares throughout the year from Calgary to New York City down to $354 roundtrip after taxes.

Cheap dates are available in every month between April 2013 and February 2014!

Philadelphia has also dropped to a similar price level on United, throughout the year.

Update March 21: Wow, United's prices have dropped even a little further, down to $330 roundtrip after taxes to New York and Philadelphia.

Direct flights to Chicago have also dropped to a pretty decent price of around $360, on Air Canada and WestJet, between now and June.

The easiest way to find the cheap date combinations is using Google Flights Explorer.

Use 'United States' as your destination.

Screenshot from Google Flights Explorer:


NOTE: Google Flights Explorer only displays fares up to about 6 months ahead. If you're looking for flights in October and later, try a 3 day flexible date search on Kayak to see what's available.

As is usually the case with these unadvertised drops on United, it's hard to say when they'll put the price back up.

Hit Like if you like this deal! Click Share to show your friends on Facebook.



2012
5
April
Calgary to Chicago - $291 roundtrip after taxes!

The WestJet Blue Tag Thursday deals have been kind of ho-hum lately, but they dropped a *really* exciting one today! I believe this is as cheap as I've ever seen to Chicago from Calgary. Ever.

Read more



2011
12
September
Kalispell to Chicago - $200 roundtrip after taxes - any date

While I do watch for interesting fares out of Montana, the truth is that it's pretty rare to see one that's worth the drive. Allegiant Air has cheap flights to Vegas, but on the major airlines, prices from Montana aren't usually significantly better to warrant the 5 hour drive from Calgary. We're not like Toronto where we can hop across the border to Buffalo. Flying out of the U.S. for us is a significant investment of time.

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2011
28
June
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.

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2011
19
May
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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2011
20
April
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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2011
9
March
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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2010
7
August
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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