ShonTron
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One thing i love about Chicago is they have lots of hotels to choose from for all budgets. I have been to Chicago many times for business, conventions, and for vacations. You don't have to break the bank to stay in the downtown. Toronto has lost a lot of mid level hotel rooms, forcing my friends who visit and business clients stay outside the downtown. Not everyone can afford 4 or 5 star hotel that goes for $300 to 600 a night room for a week or two. Even NYC has added a huge number of budget friendly hotels over the past few years.
Less room at the inn for Toronto conventions: Report
Booming downtown development is threatening the future of the city’s thriving convention business as mid-priced hotels are converted to condos and others are rebranded and renovated to justify higher nightly rates.
https://www.thestar.com/business/2018/07/17/less-room-at-the-inn-for-toronto-conventions-report.html
Hotel-to-condo developments are threatening Toronto’s convention business: report
https://www.theglobeandmail.com/can...lopments-are-threatening-torontos-convention/
Montreal too! Even on Civic Holiday weekend (with the womens' tennis matches and the Osheaga music festival going on) I was able to find a hotel room for less than $200/night, in Griffintown.
And unless you're going to New York during a major convention or around the Christmas holidays, hotels can often be surprisingly inexpensive because of the huge capacity and good mix of hotel room classes. There are also hotel clusters just outside Manhattan, like in Long Island City, that are easily accessible to everything by subway. Toronto doesn't really have any alternative hotel clusters like that. The airport is too far and UP Express too expensive to qualify. Chicago does have the Midway Airport hotel cluster which is a bit more convenient with the L service.