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Saturday, November 28th 2020

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

2-in-1 trip: Winnipeg to Chicago and San Juan, Puerto Rico - $379 CAD roundtrip including taxes

Chicago, Illinois and San Juan, Puerto Rico

United Airlines is showing 2-in-1 flights that allow you to spend time in both Chicago and San Juan, Puerto Rico for a total price of $379 CAD roundtrip including taxes.

The available dates are in winter months, so while it's a desirable time to visit Puerto Rico - it's likely to be pretty cold in Chicago.

It would normally cost a minimum of about $1200 to fly to both destinations separately from Winnipeg.

You can also book these as a regular roundtrip flight from Winnipeg to only San Juan, Puerto Rico - but it requires an overnight stay in Chicago on the way there.

Puerto Rico was devastated by Hurricane Maria in September 2017. Recently, 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

January, February 2019

How to find and book this deal

1. Go to FlightHub

2. Change the search type to 'Multi-City'

3. Search for a flight like this one:

Winnipeg (YWG) to Chicago (ORD)
Chicago (ORD) to San Juan, Puerto Rico (SJU)
San Juan, Puerto Rico (SJU) to Winnipeg (YWG)

- Try one of the following date combinations...


Jan 10 to Jan 13 to Jan 20
Jan 17 to Jan 20 to Jan 27
Jan 24 to Jan 27 to Feb 3
Jan 30 to Feb 3 to Feb 9

Feb 6 to Feb 10 to Feb 17

screenshot from FlightHub.com

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