Flights to Chicago from CAD201*
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1 Passenger
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Great deals to Chicago
CAD
| From | To | Dates | Fare Type | Price |
|---|---|---|---|---|
Toronto (YTZ) | Chicago (MDW) | Jun 22, 2026 | One-way fare/Economy | |
Toronto (YTO) | Chicago (MDW) | Jun 24, 2026 | One-way fare/Economy | |
Ottawa (YOW) | Chicago (MDW) | Jun 11, 2026 | One-way fare/Economy | |
Montreal (YUL) | Chicago (MDW) | Jul 27, 2026 | One-way fare/Economy | |
Halifax (YHZ) | Chicago (MDW) | Jun 14, 2026 | One-way fare/Economy | |
Montreal (YHU) | Chicago (MDW) | Jun 19, 2026 | One-way fare/Economy | |
Fredericton (YFC) | Chicago (MDW) | Jun 24, 2026 | One-way fare/Economy | |
Thunder Bay (YQT) | Chicago (MDW) | Jun 19, 2026 | One-way fare/Economy | |
Moncton (YQM) | Chicago (MDW) | Aug 06, 2026 | One-way fare/Economy | |
Sault Ste. Marie (YAM) | Chicago (MDW) | Aug 02, 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.
Test Mosaic Grid Title
CAD
From Toronto (YTZ) to Chicago (MDW)
Jun 04, 2026
Starting from
CAD201*
Seen:13hoursago
One-way fare/Economy
From Toronto (YTO) to Chicago (MDW)
May 23, 2026
Starting from
CAD202*
Seen:21hoursago
One-way fare/Economy
From Montreal (YUL) to Chicago (MDW)
Jun 04, 2026
Starting from
CAD249*
Seen:3daysago
One-way fare/Economy
From Ottawa (YOW) to Chicago (MDW)
Jun 04, 2026
Starting from
CAD300*
Seen:1dayago
One-way fare/Economy
From Halifax (YHZ) to Chicago (MDW)
May 26, 2026
Starting from
CAD345*
Seen:4daysago
One-way fare/Economy
From Fredericton (YFC) to Chicago (MDW)
May 21, 2026
Starting from
CAD381*
Seen:2daysago
One-way fare/Economy
From Moncton (YQM) to Chicago (MDW)
May 21, 2026
Starting from
CAD389*
Seen:2daysago
One-way fare/Economy
From Sault Ste. Marie (YAM) to Chicago (MDW)
May 17, 2026
Starting from
CAD422*
Seen:2daysago
One-way fare/Economy
From Thunder Bay (YQT) to Chicago (MDW)
May 31, 2026
Starting from
CAD404*
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.
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CAD
Vancouver (YVR)to
Toronto (YYZ)Depart Jul 09, 2026Starting fromCAD183Seen: 1 hour agoOne-way fareEconomyVancouver (YVR)to
Toronto (YTO)Depart Jul 10, 2026Starting fromCAD183Seen: 2 minutes agoOne-way fareEconomyEdmonton (YEG)to
Toronto (YYZ)Depart May 21, 2026Starting fromCAD196Seen: 3 hours agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YTO)Depart Jun 12, 2026Starting fromCAD118Seen: 4 hours agoOne-way fareEconomyCalgary (YYC)to
Toronto (YYZ)Depart Jun 05, 2026Starting fromCAD173Seen: 33 minutes agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YYZ)Depart Jun 17, 2026Starting fromCAD118Seen: 1 hour agoOne-way fareEconomyThunder Bay (YQT)to
Toronto (YTZ)Depart Jun 02, 2026Starting fromCAD204Seen: 1 hour agoOne-way fareEconomyCalgary (YYC)to
Toronto (YTO)Depart Sep 08, 2026Starting fromCAD171Seen: 1 hour agoOne-way fareEconomyOttawa (YOW)to
Toronto (YTZ)Depart Jun 18, 2026Starting fromCAD149Seen: 13 hours agoOne-way fareEconomyThunder Bay (YQT)to
Toronto (YTO)Depart Jun 23, 2026Starting fromCAD191Seen: 1 hour agoOne-way fareEconomySt. John's, NL (YYT)to
Toronto (YYZ)Depart Jun 17, 2026Starting fromCAD181Seen: 47 minutes agoOne-way fareEconomyEdmonton (YEG)to
Toronto (YTO)Depart May 20, 2026Starting fromCAD196Seen: 19 minutes agoOne-way fareEconomyVictoria (YYJ)to
Toronto (YYZ)Depart Jul 07, 2026Starting fromCAD263Seen: 28 minutes agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YTZ)Depart May 30, 2026Starting fromCAD118Seen: 7 minutes agoOne-way fareEconomyWinnipeg (YWG)to
Toronto (YYZ)Depart Jun 09, 2026Starting fromCAD123Seen: 9 hours agoOne-way fareEconomyNew York (EWR)to
Toronto (YTZ)Depart Jun 04, 2026Starting fromCAD160Seen: 2 hours agoOne-way fareEconomyBoston (BOS)to
Toronto (YTZ)Depart Aug 18, 2026Starting fromCAD155Seen: 15 hours agoOne-way fareEconomyOttawa (YOW)to
Toronto (YTO)Depart May 31, 2026Starting fromCAD120Seen: 7 hours agoOne-way fareEconomyMontreal (YUL)to
Toronto (YTZ)Depart Aug 08, 2026Starting fromCAD171Seen: 19 hours agoOne-way fareEconomySt. John's, NL (YYT)to
Toronto (YTO)Depart Jun 11, 2026Starting fromCAD181Seen: 34 minutes agoOne-way fareEconomy
This is the disclaimer.
URL Parameter Context to Context - Mary
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flight_land
CAD
Toronto (YTZ)to
Chicago (MDW)Depart Jun 23, 2026
Starting from
CAD201
Seen: 13 hours ago
One-way fare
Economy
Toronto (YTO)to
Chicago (MDW)Depart May 23, 2026
Starting from
CAD202
Seen: 21 hours ago
One-way fare
Economy
Toronto (YTZ)to
Chicago (ORD)Depart Sep 07, 2026
Starting from
CAD206
Seen: 15 hours ago
One-way fare
Economy
Montreal (YUL)to
Chicago (MDW)Depart Jul 27, 2026
Starting from
CAD273
Seen: 1 day ago
One-way fare
Economy
Ottawa (YOW)to
Chicago (MDW)Depart Jun 04, 2026
Starting from
CAD300
Seen: 1 day ago
One-way fare
Economy
Halifax (YHZ)to
Chicago (MDW)Depart Jun 14, 2026
Starting from
CAD303
Seen: 1 day ago
One-way fare
Economy
Montreal (YHU)to
Chicago (MDW)Depart Jun 21, 2026
Starting from
CAD243
Seen: 1 day ago
One-way fare
Economy
Montreal (YHU)to
Chicago (ORD)Depart Sep 25, 2026
Starting from
CAD267
Seen: 1 day ago
One-way fare
Economy
Thunder Bay (YQT)to
Chicago (MDW)Depart Jun 19, 2026
Starting from
CAD347
Seen: 17 hours ago
One-way fare
Economy
Sault Ste. Marie (YAM)to
Chicago (MDW)Depart Aug 02, 2026
Starting from
CAD338
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 Jul 02, 2026 | Starting from CAD214 Seen: 1 hour ago |
| Toronto (YYZ) | Calgary (YYC) | One-way fare / Economy | Depart Sep 08, 2026 | Starting from CAD184 Seen: 22 minutes ago |
| Toronto (YTO) | Vancouver (YVR) | One-way fare / Economy | Depart Jul 08, 2026 | Starting from CAD202 Seen: 36 minutes ago |
| Toronto (YTO) | Halifax (YHZ) | One-way fare / Economy | Depart May 30, 2026 | Starting from CAD111 Seen: 41 minutes ago |
| Vancouver (YVR) | Toronto (YYZ) | One-way fare / Economy | Depart Jul 07, 2026 | Starting from CAD183 Seen: 1 hour ago |
| Toronto (YYZ) | Halifax (YHZ) | One-way fare / Economy | Depart Jun 04, 2026 | Starting from CAD124 Seen: 33 minutes ago |
| Ottawa (YOW) | Halifax (YHZ) | One-way fare / Economy | Depart Jun 05, 2026 | Starting from CAD219 Seen: 1 hour ago |
| Toronto (YTO) | Calgary (YYC) | One-way fare / Economy | Depart Jul 09, 2026 | Starting from CAD163 Seen: 1 hour ago |
| Ottawa (YOW) | Vancouver (YVR) | One-way fare / Economy | Depart Jun 21, 2026 | Starting from CAD236 Seen: 1 hour ago |
| Toronto (YYZ) | Las Vegas (LAS) | One-way fare / Economy | Depart Dec 07, 2026 | Starting from CAD232 Seen: 22 hours ago |
| Vancouver (YVR) | Toronto (YTO) | One-way fare / Economy | Depart Jul 10, 2026 | Starting from CAD183 Seen: 2 minutes ago |
| Hamilton, CA (YHM) | Halifax (YHZ) | One-way fare / Economy | Depart May 30, 2026 | Starting from CAD112 Seen: 17 minutes ago |
| Ottawa (YOW) | Calgary (YYC) | One-way fare / Economy | Depart Jun 15, 2026 | Starting from CAD163 Seen: 2 hours ago |
| Edmonton (YEG) | Toronto (YYZ) | One-way fare / Economy | Depart May 29, 2026 | Starting from CAD196 Seen: 54 minutes ago |
| Halifax (YHZ) | Toronto (YTO) | One-way fare / Economy | Depart Jun 12, 2026 | Starting from CAD118 Seen: 4 hours ago |
| Hamilton, CA (YHM) | Vancouver (YVR) | One-way fare / Economy | Depart Jul 08, 2026 | Starting from CAD203 Seen: 5 minutes ago |
| Toronto (YYZ) | Edmonton (YEG) | One-way fare / Economy | Depart Jun 05, 2026 | Starting from CAD204 Seen: 3 hours ago |
| Calgary (YYC) | Toronto (YYZ) | One-way fare / Economy | Depart May 29, 2026 | Starting from CAD173 Seen: 39 minutes ago |
| Halifax (YHZ) | Ottawa (YOW) | One-way fare / Economy | Depart Jun 02, 2026 | Starting from CAD213 Seen: 2 minutes ago |
| Halifax (YHZ) | Toronto (YYZ) | One-way fare / Economy | Depart Jun 17, 2026 | Starting from CAD118 Seen: 1 hour ago |
URL Parameter All to All - Mary