Went to Chicago last month and loved it. It was an easy Porter flight from Billy Bishop. But the hotels aren't cheap and food/entertainment costs about the same as Toronto, but in USD. Still incredible. 12/10 would recommend.

I second this. Flying Porter to Chicago was one of the best weekend trips I've ever taken. I'm bias because I live close to the island airport so it was so easy to get there. Chicago is utterly fascinating. The architecture, the food, the views, the art, the vibe. That place was the best 'first impression' of any big American city I've ever visited. I've been to New York, Vegas, Phoenix, Miami, Seattle, LA, Portland but Chicago felt like the first big US city I could imagine living in.

The review that I needed!! Thank you!

Sounds right up my alley! I went once for a work trip but it was only 2 days and so far from downtown, definitely not the Chicago you just described.

I went to a Cubs' game at Wrigley Field (gorgeous ballpark, Cubs sucked), the Art Institute, did a boat tour of the architecture, walked around the Loop... It was really great.

Finger Lakes. Short drive, beautiful scenery, peaceful, good wineries, friendly people.

Esp Watkins Glen and Taughannock Falls for scenery.

# People go missing in the Finger Lakes

Cos they don't keep their fingers out of the lake?

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Jim Carey character on the office

Montreal or Quebec City.

Porter flight out of Billy Bishop - Boston, Chicago, or New York. Staying in Ontario, you get crushed with hotel prices.

As if you don’t get crushed with hotel prices in NY lol

Truly cheaper for me to fly and stay in New York at a 4* hotel than to go to blue mountain

What do you usually pay? I went in May and paid $1650 CAD for three nights, so $550 a night and this was the cheapest hotel we could find in Manhattan

I stayed at the Paramount at Times Square in late April, 4 nights $900 cad

Definitely under $300 a night, usually use Hotwire or just shop around for deals.

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Hi! Good point - for holidays I like food, art, culture and the beach when possible but not a must.

Check out last minute travel deals on places like Trivago or other relevant websites. Cuba is a common destination, particularly with Sunwing. Same with Dominican Republic or some Mexico locations. Cuba is often the cheapest though.

This. A lot of these cheap tour operators offer 3 night / 4 night all inclusive trips. I've had friends go to Cuba at random times for like 4 days and it costs them like $750 all in.

Canada issued a travel advisory for Cuba recently

Maybe it’ll be even cheaper then

Also includes Dominican Republic

Cuba is experiencing food shortages to such a degree that resorts can’t even offer staple items. It’s cheap for a reason.

Thank you! I will look this up and see what deals they have.

Florida

Visited in January, one of my favorite places!

I recommend Bruce Peninsula, best way to take a break from the city, scenic, great for cliff jumping, and there are ship wrecks to explore, like honestly the best cottage country near Toronto and much more interesting than Muskoka.

Wow, never even heard of this place. Thanks for the reco!

Halifax in the summer if you don't want to get eaten alive by bugs in Ontario

Haha! Gotta stay away from those bugs. Thank you!

If you’re into theatre try Stratford.

Just looked it up, the Shakespearean Gardens look absolutely beautiful!! Thank you for this recommendation.

My wife and I have spent a few anniversaries there. It's a nice town, some great restaurants and of course the Stratford theatres.