Weekend trips from Toronto under C$500
For each of the coming weekends, the cheapest return we hold from Toronto to each place: out on a Thursday, Friday or Saturday and back on the Sunday or Monday, with at least a full day there.
Places with a weekend trip: 11
Weekends covered: 8
Weekend of Sat 24 Oct
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | C$309 (US$218) | Fri 23 Oct 15:20 | Mon 26 Oct 17:55 | 2 weekdays | YYZ → LGA | out nonstop, back nonstop | Porter Airlines Canada | found 2 days ago | See prices for these dates | Check today's price |
| Boston | C$474 (US$335) | Thu 22 Oct 18:00 | Sun 25 Oct 19:50 | 1 weekday | YTZ → BOS | out nonstop, back nonstop | Porter Airlines Canada | found 3 days ago | See prices for these dates | Check today's price |
Weekend of Sat 31 Oct
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Halifax | C$273 (US$193) | Thu 29 Oct 14:30 | Mon 2 Nov 22:05 | 3 weekdays | YYZ → YHZ | out nonstop, back nonstop | Flair Airlines | found 8 hours ago | See prices for these dates | Check today's price |
| Calgary | C$365 (US$258) | Sat 31 Oct 21:05 | Mon 2 Nov 13:20 | 1 weekday | YYZ → YYC | out nonstop, back nonstop | Flair Airlines | found yesterday | See prices for these dates | Check today's price |
| Vancouver | C$452 (US$319) | Sat 31 Oct 21:00 | Mon 2 Nov 16:53 | 1 weekday | YYZ → YVR | out nonstop, back nonstop | Flair Airlines | found yesterday | See prices for these dates | Check today's price |
| New York | C$476 (US$336) | Fri 30 Oct 19:10 | Sun 1 Nov 09:39 | None | YTZ → EWR | out nonstop, back nonstop | Porter Airlines Canada | found yesterday | See prices for these dates | Check today's price |
| Georgetown | C$333 (US$235) | Thu 29 Oct 10:15 | Sun 1 Nov 15:35 | 2 weekdays | YYZ → GCM | out nonstop, back nonstop | WestJet | found 3 days ago | See prices for these dates | Check today's price |
| Fort Lauderdale | C$354 (US$250) | Fri 30 Oct 15:35 | Sun 1 Nov 20:52 | 1 weekday | YYZ → FLL | out 1 stop, back 1 stop | United Airlines | found 6 days ago | See prices for these dates | Check today's price |
Weekend of Sat 7 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Halifax | C$221 (US$156) | Thu 5 Nov 14:30 | Mon 9 Nov 22:05 | 3 weekdays | YYZ → YHZ | out nonstop, back nonstop | Flair Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Calgary | C$263 (US$186) | Fri 6 Nov 09:10 | Mon 9 Nov 06:00 | 2 weekdays | YYZ → YYC | out 1 stop, back nonstop | WestJet | found 5 days ago | See prices for these dates | Check today's price |
| Montreal | C$343 (US$242) | Fri 6 Nov 18:45 | Mon 9 Nov 18:05 | 1 weekday | YTZ → YHU | out nonstop, back nonstop | Porter Airlines Canada | found 5 days ago | See prices for these dates | Check today's price |
| Vancouver | C$360 (US$254) | Thu 5 Nov 21:00 | Mon 9 Nov 01:15 | 2 weekdays | YYZ → YVR | out nonstop, back nonstop | Flair Airlines | found 6 days ago | See prices for these dates | Check today's price |
| Chicago | C$422 (US$298) | Sat 7 Nov 10:30 | Sun 8 Nov 18:20 | None | YTZ → ORD | out nonstop, back nonstop | Porter Airlines | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 14 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | C$310 (US$219) | Fri 13 Nov 16:30 | Sun 15 Nov 08:00 | 1 weekday | YTZ → EWR | out nonstop, back nonstop | Porter Airlines Canada | found 9 hours ago | See prices for these dates | Check today's price |
| Halifax | C$238 (US$168) | Thu 12 Nov 14:30 | Sun 15 Nov 11:00 | 2 weekdays | YYZ → YHZ | out nonstop, back nonstop | Flair Airlines | found 4 days ago | See prices for these dates | Check today's price |
| Montreal | C$328 (US$231) | Fri 13 Nov 06:05 | Sun 15 Nov 17:10 | 1 weekday | YHM → YHU | out nonstop, back nonstop | Porter Airlines Canada | found 4 days ago | See prices for these dates | Check today's price |
| Boston | C$391 (US$276) | Sat 14 Nov 07:20 | Sun 15 Nov 09:50 | None | YYZ → BOS | out nonstop, back nonstop | Porter Airlines Canada | found 6 days ago | See prices for these dates | Check today's price |
| Chicago | C$396 (US$280) | Fri 13 Nov 10:30 | Mon 16 Nov 18:20 | 2 weekdays | YTZ → ORD | out nonstop, back nonstop | Porter Airlines Canada | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 21 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| New York | C$314 (US$222) | Fri 20 Nov 07:35 | Sun 22 Nov 08:00 | 1 weekday | YTZ → EWR | out nonstop, back nonstop | Porter Airlines Canada | found today | See prices for these dates | Check today's price |
| Vancouver | C$328 (US$232) | Fri 20 Nov 21:00 | Mon 23 Nov 17:55 | 1 weekday | YYZ → YVR | out nonstop, back nonstop | Flair Airlines | found today | See prices for these dates | Check today's price |
| Halifax | C$205 (US$145) | Sat 21 Nov 07:00 | Mon 23 Nov 22:05 | 1 weekday | YYZ → YHZ | out nonstop, back nonstop | Flair Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Winnipeg | C$212 (US$150) | Fri 20 Nov 07:25 | Sun 22 Nov 19:55 | 1 weekday | YYZ → YWG | out nonstop, back nonstop | Flair Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Cancun | C$399 (US$282) | Fri 20 Nov 15:40 | Mon 23 Nov 12:00 | 2 weekdays | YYZ → CUN | out nonstop, back nonstop | WestJet | found 4 days ago | See prices for these dates | Check today's price |
Weekend of Sat 28 Nov
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Vancouver | C$309 (US$218) | Thu 26 Nov 21:00 | Mon 30 Nov 01:15 | 2 weekdays | YYZ → YVR | out nonstop, back nonstop | Flair Airlines | found 2 days ago | See prices for these dates | Check today's price |
| Montreal | C$313 (US$221) | Fri 27 Nov 09:05 | Sun 29 Nov 08:25 | 1 weekday | YTZ → YHU | out nonstop, back nonstop | WestJet | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 12 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Calgary | C$335 (US$237) | Thu 10 Dec 06:05 | Sun 13 Dec 19:00 | 2 weekdays | YHM → YYC | out 1 stop, back 1 stop | Porter Airlines Canada | found 5 days ago | See prices for these dates | Check today's price |
Weekend of Sat 26 Dec
| City | From | Out | Back | Weekdays off | Airports | Stops | Airline | Found | ||
|---|---|---|---|---|---|---|---|---|---|---|
| Montreal | C$372 (US$263) | Thu 24 Dec 09:05 | Sun 27 Dec 19:35 | 2 weekdays | YTZ → YHU | out nonstop, back nonstop | Air Transat | found 16 hours ago | See prices for these dates | Check today's price |
| New York | C$449 (US$317) | Fri 25 Dec 18:20 | Sun 27 Dec 09:40 | None | YYZ → LGA | out nonstop, back nonstop | Air Transat | found 5 days ago | See prices for these dates | Check today's price |
Every trip here gives at least 24 hours at the destination and gets you home by 6 am on the Tuesday. Times are local to each airport. "Weekdays off" counts Monday to Friday days the trip takes; a flight leaving at 5 pm or later does not take that day.
1 traveler · Economy
Prices are what travelers' searches on Aviasales found in the last 7 days: the price the seller showed on Aviasales; bags may cost extra. Canadian dollars at the Bank of Canada rate of 2026-10-16, US dollars in brackets. Fares change, so check today's price before you book. How our prices work