Book Porter flights from Chicago to Canada starting at CAD130*
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Great deals from Chicago to Canada
CAD
| From | To | Dates | Fare Type | Price |
|---|---|---|---|---|
Chicago (MDW) | Toronto (YTZ) | Apr 18, 2026 | One-way fare/Economy | |
Chicago (MDW) | Toronto (YTO) | Jun 03, 2026 | One-way fare/Economy | |
Chicago (MDW) | Halifax (YHZ) | Apr 25, 2026 | One-way fare/Economy | |
Chicago (MDW) | Ottawa (YOW) | Apr 24, 2026 | One-way fare/Economy | |
Chicago (MDW) | Montreal (YUL) | Jun 02, 2026 | One-way fare/Economy | |
Chicago (MDW) | Fredericton (YFC) | May 12, 2026 | One-way fare/Economy | |
Chicago (MDW) | Windsor (YQG) | Apr 29, 2026 | One-way fare/Economy | |
Chicago (MDW) | Moncton (YQM) | May 11, 2026 | One-way fare/Economy | |
Chicago (MDW) | Thunder Bay (YQT) | Apr 28, 2026 | One-way fare/Economy | |
Chicago (MDW) | Timmins (YTS) | Apr 28, 2026 | One-way fare/Economy |
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
Great deals from Chicago to Canada
CAD
From Chicago (MDW) to Toronto (YTZ)
Apr 11, 2026
Starting from
CAD146*
Seen:12hoursago
One-way fare/Economy
From Chicago (MDW) to Toronto (YTO)
Apr 07, 2026
Starting from
CAD146*
Seen:18hoursago
One-way fare/Economy
From Chicago (MDW) to Halifax (YHZ)
Apr 11, 2026
Starting from
CAD177*
Seen:2daysago
One-way fare/Economy
From Chicago (MDW) to Ottawa (YOW)
Apr 10, 2026
Starting from
CAD242*
Seen:11hoursago
One-way fare/Economy
From Chicago (MDW) to Montreal (YUL)
Apr 10, 2026
Starting from
CAD149*
Seen:1dayago
One-way fare/Economy
From Chicago (MDW) to Sault Ste. Marie (YAM)
Mar 21, 2026
Starting from
CAD741*
Seen:1dayago
One-way fare/Economy
From Chicago (MDW) to Moncton (YQM)
Mar 21, 2026
Starting from
CAD406*
Seen:4daysago
One-way fare/Economy
*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking. Learn more about this offer. Additional baggage fees and charges for optional products and services may apply.
URL Parameter Context to Context - Mary
flight_takeoff
flight_land
CAD
Chicago (MDW)to
Toronto (YTZ)Depart Apr 18, 2026
Starting from
CAD140
Seen: 22 hours ago
One-way fare
Economy
Chicago (MDW)to
Toronto (YTO)Depart May 26, 2026
Starting from
CAD140
Seen: 1 day ago
One-way fare
Economy
Chicago (MDW)to
Halifax (YHZ)Depart May 27, 2026
Starting from
CAD177
Seen: 19 hours ago
One-way fare
Economy
Chicago (MDW)to
Ottawa (YOW)Depart Apr 10, 2026
Starting from
CAD242
Seen: 11 hours ago
One-way fare
Economy
Chicago (MDW)to
Montreal (YUL)Depart Jun 07, 2026
Starting from
CAD130
Seen: 12 hours ago
One-way fare
Economy
Chicago (ORD)to
Halifax (YHZ)Depart Sep 08, 2026
Starting from
CAD210
Seen: 1 day ago
One-way fare
Economy
Chicago (ORD)to
Toronto (YTZ)Depart Sep 07, 2026
Starting from
CAD139
Seen: 8 hours ago
One-way fare
Economy
Chicago (MDW)to
Sault Ste. Marie (YAM)Depart Mar 21, 2026
Starting from
CAD741
Seen: 1 day ago
One-way fare
Economy
Chicago (MDW)to
Fredericton (YFC)Depart May 19, 2026
Starting from
CAD366
Seen: 14 hours ago
One-way fare
Economy
Chicago (MDW)to
Moncton (YQM)Depart May 11, 2026
Starting from
CAD298
Seen: 22 hours ago
One-way fare
Economy
Chicago (ORD)to
Ottawa (YOW)Depart Apr 11, 2026
Starting from
CAD356
Seen: 1 day ago
One-way fare
Economy
Chicago (ORD)to
Montreal (YUL)Depart Oct 12, 2026
Starting from
CAD195
Seen: 1 day ago
One-way fare
Economy
URL Parameter Context to Context - Mary
URL Parameter All to All - Mary
From | To | Fare Type | Dates | Price |
|---|---|---|---|---|
| Toronto (YYZ) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 13, 2026 | Starting from CAD186 Seen: 22 minutes ago |
| Toronto (YYZ) | Las Vegas (LAS) | One-way fare / Economy | Depart Apr 10, 2026 | Starting from CAD207 Seen: 1 hour ago |
| Toronto (YTO) | Vancouver (YVR) | One-way fare / Economy | Depart May 20, 2026 | Starting from CAD156 Seen: 1 hour ago |
| Toronto (YYZ) | Calgary (YYC) | One-way fare / Economy | Depart Apr 22, 2026 | Starting from CAD170 Seen: 27 minutes ago |
| Toronto (YYZ) | Fort Lauderdale (FLL) | One-way fare / Economy | Depart Apr 20, 2026 | Starting from CAD213 Seen: 1 hour ago |
| Vancouver (YVR) | Toronto (YYZ) | One-way fare / Economy | Depart Jun 16, 2026 | Starting from CAD146 Seen: 59 minutes ago |
| Toronto (YTO) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 16, 2026 | Starting from CAD111 Seen: 6 minutes ago |
| Ottawa (YOW) | Fort Lauderdale (FLL) | One-way fare / Economy | Depart Apr 06, 2026 | Starting from CAD229 Seen: 12 minutes ago |
| Ottawa (YOW) | Orlando (MCO) | One-way fare / Economy | Depart Jun 08, 2026 | Starting from CAD229 Seen: 1 hour ago |
| Ottawa (YOW) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 22, 2026 | Starting from CAD228 Seen: 29 minutes ago |
| Halifax (YHZ) | Toronto (YTO) | One-way fare / Economy | Depart Apr 18, 2026 | Starting from CAD118 Seen: 6 minutes ago |
| Toronto (YYZ) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 15, 2026 | Starting from CAD124 Seen: 22 minutes ago |
| Ottawa (YOW) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 23, 2026 | Starting from CAD230 Seen: 55 minutes ago |
| Toronto (YYZ) | Orlando (MCO) | One-way fare / Economy | Depart Apr 05, 2026 | Starting from CAD214 Seen: 7 minutes ago |
| Hamilton, CA (YHM) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 21, 2026 | Starting from CAD149 Seen: 1 hour ago |
| Ottawa (YOW) | Calgary (YYC) | One-way fare / Economy | Depart Jun 25, 2026 | Starting from CAD208 Seen: 9 hours ago |
| Halifax (YHZ) | Orlando (MCO) | One-way fare / Economy | Depart Jun 08, 2026 | Starting from CAD220 Seen: 1 day ago |
| Toronto (YTO) | Calgary (YYC) | One-way fare / Economy | Depart Apr 09, 2026 | Starting from CAD135 Seen: 30 minutes ago |
| Vancouver (YVR) | Toronto (YTO) | One-way fare / Economy | Depart Jun 16, 2026 | Starting from CAD146 Seen: 1 hour ago |
| Halifax (YHZ) | Ottawa (YOW) | One-way fare / Economy | Depart Apr 05, 2026 | Starting from CAD222 Seen: 19 minutes ago |
URL Parameter All to All - Mary