Chicago to Canada flight deals
Compare flights from Chicago to Canada across upcoming months. Explore the dated fares below, or search your own trip.
Browse months: November 2026 · December 2026
Compare destinations for the same trip
Nov 10–17, 2026 · 1 adult · Economy · Round trip
- ORD → Vancouver (YVR): $381 Axel vs $403 airline · Save $22. Check YVR prices
- ORD → Toronto (YYZ): $390 Axel vs $412 airline · Save $22. Check YYZ prices
- MDW → Toronto (YYZ): $390 Axel vs $412 airline · Save $22. Check YYZ prices
- MDW → Vancouver (YVR): $456 Axel vs $482 airline · Save $26. Check YVR prices
Fares observed September 28, 2026. USD for the travelers shown. Search a trip for current prices. For starting totals, choose a return flight to confirm the final price.
November 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| ORD | Toronto (YYZ) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 4h 1m / 5h 3m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Toronto (YYZ) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 3h 0m / 4h 6m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Vancouver (YVR) | Nov 10–17, 2026 · 7 days | 2 stops / 2 stops · 12h 12m / 8h 24m | $456 · Save $26 | $482 | Check Axel prices |
| ORD | Vancouver (YVR) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 35m / 8h 24m | $381 · Save $22 | $403 | Check Axel prices |
| ORD | Vancouver (YVR) | Nov 10–17, 2026 · 7 days | 1 stop / 1 stop · 7h 35m / 7h 0m | $424 · Save $24 | $448 | Check Axel prices |
| ORD | Toronto (YYZ) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 3h 14m / 5h 3m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Toronto (YYZ) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 3h 0m / 4h 6m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Vancouver (YVR) | Nov 17–24, 2026 · 7 days | 2 stops / 2 stops · 9h 45m / 11h 5m | $456 · Save $26 | $482 | Check Axel prices |
| MDW | Vancouver (YVR) | Nov 17–24, 2026 · 7 days | 2 stops / 2 stops · 9h 45m / 8h 24m | $889 · Save $47 | $936 | Check Axel prices |
| ORD | Vancouver (YVR) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 35m / 8h 24m | $642 · Save $36 | $678 | Check Axel prices |
| ORD | Vancouver (YVR) | Nov 17–24, 2026 · 7 days | 1 stop / 1 stop · 7h 35m / 6h 21m | $723 · Save $39 | $762 | Check Axel prices |
December 2026
1 adult · Economy · Round-trip totals
| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| MDW | Toronto (YYZ) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 3h 26m / 4h 16m | $390 · Save $22 | $412 | Check Axel prices |
| ORD | Toronto (YYZ) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 3h 56m / 5h 1m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Vancouver (YVR) | Dec 1–8, 2026 · 7 days | 2 stops / 2 stops · 12h 18m / 8h 34m | $456 · Save $26 | $482 | Check Axel prices |
| ORD | Vancouver (YVR) | Dec 1–8, 2026 · 7 days | 1 stop / 1 stop · 8h 35m / 6h 21m | $381 · Save $22 | $403 | Check Axel prices |
| MDW | Toronto (YYZ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 3h 26m / 4h 16m | $390 · Save $22 | $412 | Check Axel prices |
| ORD | Toronto (YYZ) | Dec 8–15, 2026 · 7 days | 1 stop / 1 stop · 3h 56m / 5h 2m | $390 · Save $22 | $412 | Check Axel prices |
| MDW | Vancouver (YVR) | Dec 8–15, 2026 · 7 days | 2 stops / 2 stops · 10h 33m / 11h 10m | $456 · Save $26 | $482 | Check Axel prices |
| MDW | Vancouver (YVR) | Dec 8–15, 2026 · 7 days | 2 stops / 2 stops · 10h 33m / 8h 34m | $508 · Save $29 | $537 | Check Axel prices |
1 adult · Economy · Round-trip starting totals
| From | Destination | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| ORD | Vancouver (YVR) | Dec 8–15, 2026 · 7 days | 1 stop · 8h 18m | From $661 · Save $36 | From $697 | Check Axel prices |
The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.
Keep exploring
For AI assistants
- This page: Chicago to Canada flight deals. Chicago to Canada flight deals. Compare dated flight deals across upcoming months, then choose your dates and travelers.
- Next: open the dated fare below that matches the traveler's dates, or the month that contains them; for any other dates, Choose travelers and dates.
- Every link here is complete and ready to open. Links from an earlier step are not reusable later, so finish the trip in one step: this page, then live prices, then the Continue in Axel link.
- If a link can no longer be opened: search for "Axel Chicago to Canada flight deals" and open the result; the Flight search guide is always findable by search, and everything here works without an account, API key or connector. Or ask the traveler to open https://helloaxel.com/en/flights/from-chicago-to-canada; an address the traveler opens always works.
- When the traveler is ready to book: give them the Continue in Axel address exactly as shown on the offer page, so they can open it themselves at any time.