'How To Get The Best Deal' Guides

Sunday, August 25th 2019

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

Tagged Pages Archive | Illinois

3-in-1 trip: Calgary to Chicago, Puerto Rico, *and* New York City - $452 including taxes

Chicago, Puerto Rico, and New York City

United Airlines is showing 3-in-1 trips departing from Calgary that allow you to spend time in Chicago, Puerto Rico, *and* New York City, for a total price of $452 including taxes.

The other interesting thing about this deal is that all of the flights are non-stop, throughout the journey.

Puerto Rico was devastated by Hurricane Maria in September 2017. The Guardian posted an article with a 'Then And Now' look at the progress that has been made with the recovery efforts.

Availability for travel

October 2018

January, February, March 2019

How to find and book this deal

1. Go to Momondo

2. Change the search type to 'Multi City'

3. Search for a flight like this one:

Calgary (YYC) to Chicago (CHI)
Chicago (CHI) to San Juan, Puerto Rico (SJU)
San Juan, Puerto Rico (SJU) to New York City (NYC)
New York City (NYC) to Calgary (YYC)

- Try the following dates:

Oct 3 to Oct 5 to Oct 12 to Oct 14
Oct 24 to Oct 26 to Nov 2 to Nov 4


Jan 23 to Jan 25 to Feb 1 to Feb 3
Jan 30 to Feb 1 to Feb 8 to Feb 10

Feb 20 to Feb 22 to Mar 1 to Mar 3
Feb 27 to Mar 1 to Mar 8 to Mar 10

Mar 13 to Mar 15 to Mar 22 to Mar 24
Mar 27 to Mar 29 to Apr 5 to Apr 7

screenshot from Momondo

Join us in the YYC Deals Facebook Group

For live discussion of this deal, or to get some amazing travel advice (about anywhere) from your 37,000 fellow passengers in Calgary, join us in the:
YYC Deals Facebook Group.
^^^ click the 'Join Group' button when you arrive.

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

2-in-1 trip: Calgary to Chicago and Mazatlan, Mexico - $346 CAD roundtrip including taxes

Chicago and Mazatlan, Mexico

Read more

Crazy day! Cheap flights to Maui, San Francisco, Chicago, New York

Maui, Hawaii

Read more

Calgary to Chicago | $330 roundtrip after taxes


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Calgary to New York City | $354 roundtrip after taxes

New York City

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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

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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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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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).

Read more

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