1. Landside by 2330 is very likely, if without checked-in luggages. Add 20-30 minutes to get your bags back.

2. Taxi to downtown hotels will take 30~40 minutes and ~50CAD in the late evening. However, $140 or under within a walking distance from the Union Station is not likely. You can meta-search with kayak.com or hostelz.com, to balance between cost and convenience.

3. For cheaper options, consider either:
- staying near the airport and take the Airport Shuttle or TTC the next morning. or
- staying in a hostel and take a cab or subway the next morning.