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Somewhere specific you’re targeting, or just keeping an eye out for a holiday in general? A few thoughts... -as much as I’d like to recommend flying out of Brandon, most destinations make less sense financially than to fly out of Winnipeg. If you pick your spots you might do alright from Brandon for Alberta, BC or the odd time California, Arizona or Hawaii after you factor in cost of gas, parking, maybe hotel in Winnipeg. Generally the larger the group you’re flying with the more of a no brainer it becomes to fly out of Winnipeg. -Google flight has quickly become an indispensable tool for finding best destinations, dates, deals. Their map is great where you can choose a departure airport and date and get a quick visual for prices all around the globe. They’ve also recently made it easier to compare airports. So for example if going to Southern California and you don’t care which airport you fly into you can quickly see which has the better deal. Same on the departure end where you can compare for example Winnipeg, Regina, Brandon. They also give super handy graphs that show you which dates are optimal for them departure/destination you’re looking at. -Airbnb for accommodations has quickly become a goto for us both to get more space and often stay at a better price. Just be sure you read enough reviews on a place to get a real sense for strengths and weaknesses. I personally don’t book a place unless there are at least 10-15 reviews to go off of. Also be sure you’re booking a place with a cancellation policy you’re comfortable with (this info is stated on each listing) -Expedia is still handy as a way to compare all hotel options. Create an account with them to see some of the member-only rates they offer. Sometimes it’s only about $5 off per night, but every nickel counts! Once you’ve found a flight you want with Google Flight, before you book it’s worth searching Expedia for a flight+hotel package deal that includes that flight just in case they have a hotel they offer a good combined rate on. It takes time but may also be worth comparing against another site like Booking.com -if going with a hotel, before you book make sure you compare Expedia’s rate with the rate shown on the hotel’s website. Different hotel chains have different price guarantee policies that can range from giving 25% off to even free nights if you’ve found Expedia’s rate is less than the one on their site. Alternatively Expedia has a price guarantee of their own where if someone else’s price is lower than theirs they match and give you future travel credit. -also on hotels, check out Hotwire. Recently found a couple great deals that weren’t avail elsewhere. The trade off is accepting a bit of uncertainty about which exact hotel you’re booking but I’ve found if you connect enough dots between their site and other sites you can usually figure out which hotel it is -finally on hotels, Tripadvisor is your friend. Takes so much of the guesswork and uncertainty out if you spend the time to read enough reviews to get a sense for strengths and weaknesses of a place
-if you don’t care where you go and want to keep an eye on what current deals are out there, would recommend getting on Travelzoo’s Top 20 deals weekly email along with Ywgdeals.com’s email list. Both send out hand picked deals that are usually worth the time Good luck!
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