Yeah if it was in CAD, it's not bad. Seeing how its in USD makes it very pricey, especially if travelling solo. Don't like how it's non-refundable as well, since you're locked in for something all the way in August. Also, I assume it's not covering transportation to Chicago.
You can probably do it for a cheaper price if planning by yourself. If travelling solo, best to probably book a private room on AirBNB which would be half the cost of a hotel room. If going with 2-3 people, a $250-$300 CAD per night hotel split between 2-3 isn't that bad. Private cruise sounds nice, though after a game I'd be more inclined staying in Wrigleyville or going out for beers at a sports bar.
If I went with a buddy, here's a rundown on the costs:
- $300 RT flight to Chicago (would use points so would only pay the taxes)
- $250-300 for two nights of a hotel (split between a friend)
- $200 on tickets between both games
- $200 on drinks/entertainment for both nights
- $100 on food roughly (depending on what & where you eat)
- CTA 3-Day Pass is $20 USD. Other transportation with Uber pools I would say probably around $20 USD.
Anyone could probably do the trip for around $700-$800 CAD if going down with a friend which isn't bad. If going solo, best to book a private room on AirBNB since it would be far better value than a hotel.