Flights to Chicago from CAD199*
expand_more
1 Passenger
expand_morePromo Code
expand_moreexpand_more
today
fc-booking-disclaimer
Great deals to Chicago
CAD
| From | To | Dates | Fare Type | Price |
|---|---|---|---|---|
Toronto (YTZ) | Chicago (MDW) | Jun 09, 2026 | One-way fare/Economy | |
Toronto (YTO) | Chicago (MDW) | May 30, 2026 | One-way fare/Economy | |
Ottawa (YOW) | Chicago (MDW) | Apr 20, 2026 | One-way fare/Economy | |
Halifax (YHZ) | Chicago (MDW) | May 20, 2026 | One-way fare/Economy | |
Thunder Bay (YQT) | Chicago (MDW) | Apr 12, 2026 | One-way fare/Economy | |
Montreal (YUL) | Chicago (MDW) | May 29, 2026 | One-way fare/Economy | |
Moncton (YQM) | Chicago (MDW) | May 08, 2026 | One-way fare/Economy | |
Fredericton (YFC) | Chicago (MDW) | May 05, 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)
Apr 11, 2026
Starting from
CAD201*
Seen:1dayago
One-way fare/Economy
From Toronto (YTO) to Chicago (MDW)
Apr 11, 2026
Starting from
CAD196*
Seen:3daysago
One-way fare/Economy
From Ottawa (YOW) to Chicago (MDW)
Apr 09, 2026
Starting from
CAD325*
Seen:3daysago
One-way fare/Economy
From Halifax (YHZ) to Chicago (MDW)
Apr 04, 2026
Starting from
CAD245*
Seen:17hoursago
One-way fare/Economy
From Thunder Bay (YQT) to Chicago (MDW)
Apr 11, 2026
Starting from
CAD310*
Seen:3daysago
One-way fare/Economy
From Montreal (YUL) to Chicago (MDW)
Mar 26, 2026
Starting from
CAD419*
Seen:19hoursago
One-way fare/Economy
From Moncton (YQM) to Chicago (MDW)
Mar 22, 2026
Starting from
CAD467*
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.
SFM Carousel
flight_takeoff
flight_land
CAD
Vancouver (YVR)to
Toronto (YYZ)Depart Jun 18, 2026Starting fromCAD146Seen: 1 hour agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YTO)Depart Apr 19, 2026Starting fromCAD118Seen: 1 hour agoOne-way fareEconomyVancouver (YVR)to
Toronto (YTO)Depart Apr 11, 2026Starting fromCAD141Seen: 3 hours agoOne-way fareEconomyCalgary (YYC)to
Toronto (YYZ)Depart Apr 19, 2026Starting fromCAD166Seen: 4 hours agoOne-way fareEconomyEdmonton (YEG)to
Toronto (YYZ)Depart Jun 08, 2026Starting fromCAD159Seen: 4 hours agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YYZ)Depart Apr 10, 2026Starting fromCAD118Seen: 4 hours agoOne-way fareEconomyThunder Bay (YQT)to
Toronto (YTO)Depart May 29, 2026Starting fromCAD104Seen: 8 hours agoOne-way fareEconomyThunder Bay (YQT)to
Toronto (YTZ)Depart Apr 05, 2026Starting fromCAD158Seen: 5 hours agoOne-way fareEconomyOttawa (YOW)to
Toronto (YTZ)Depart Apr 23, 2026Starting fromCAD193Seen: 7 hours agoOne-way fareEconomyHalifax (YHZ)to
Toronto (YTZ)Depart Apr 14, 2026Starting fromCAD118Seen: 7 hours agoOne-way fareEconomySt. John's, NL (YYT)to
Toronto (YYZ)Depart Apr 24, 2026Starting fromCAD127Seen: 5 hours agoOne-way fareEconomySt. John's, NL (YYT)to
Toronto (YTO)Depart Apr 14, 2026Starting fromCAD127Seen: 8 hours agoOne-way fareEconomyEdmonton (YEG)to
Toronto (YTO)Depart Apr 28, 2026Starting fromCAD152Seen: 7 hours agoOne-way fareEconomyWinnipeg (YWG)to
Toronto (YTO)Depart Jun 22, 2026Starting fromCAD134Seen: 7 hours agoOne-way fareEconomyVictoria (YYJ)to
Toronto (YYZ)Depart Apr 13, 2026Starting fromCAD172Seen: 2 hours agoOne-way fareEconomyWinnipeg (YWG)to
Toronto (YYZ)Depart Apr 02, 2026Starting fromCAD134Seen: 32 minutes agoOne-way fareEconomyFort Lauderdale (FLL)to
Toronto (YYZ)Depart Aug 28, 2026Starting fromCAD133Seen: 6 hours agoOne-way fareEconomyCalgary (YYC)to
Toronto (YTO)Depart Apr 16, 2026Starting fromCAD143Seen: 4 hours agoOne-way fareEconomyBoston (BOS)to
Toronto (YTZ)Depart May 12, 2026Starting fromCAD139Seen: 8 hours agoOne-way fareEconomyNew York (EWR)to
Toronto (YTZ)Depart Apr 01, 2026Starting fromCAD129Seen: 3 hours agoOne-way fareEconomy
This is the disclaimer.
URL Parameter Context to Context - Mary
flight_takeoff
flight_land
CAD
Toronto (YTZ)to
Chicago (MDW)Depart Jun 10, 2026
Starting from
CAD201
Seen: 18 hours ago
One-way fare
Economy
Toronto (YTO)to
Chicago (MDW)Depart Apr 20, 2026
Starting from
CAD201
Seen: 14 hours ago
One-way fare
Economy
Ottawa (YOW)to
Chicago (MDW)Depart Apr 14, 2026
Starting from
CAD330
Seen: 1 day ago
One-way fare
Economy
Halifax (YHZ)to
Chicago (MDW)Depart May 20, 2026
Starting from
CAD245
Seen: 14 hours ago
One-way fare
Economy
Thunder Bay (YQT)to
Chicago (MDW)Depart Jun 18, 2026
Starting from
CAD315
Seen: 1 day ago
One-way fare
Economy
Montreal (YUL)to
Chicago (MDW)Depart May 20, 2026
Starting from
CAD199
Seen: 14 hours ago
One-way fare
Economy
Moncton (YQM)to
Chicago (MDW)Depart May 08, 2026
Starting from
CAD359
Seen: 17 hours ago
One-way fare
Economy
Toronto (YTZ)to
Chicago (ORD)Depart Sep 26, 2026
Starting from
CAD200
Seen: 9 hours ago
One-way fare
Economy
Fredericton (YFC)to
Chicago (MDW)Depart Jul 09, 2026
Starting from
CAD420
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 08, 2026 | Starting from CAD186 Seen: 25 minutes ago |
| Toronto (YYZ) | Las Vegas (LAS) | One-way fare / Economy | Depart Jun 19, 2026 | Starting from CAD207 Seen: 7 hours ago |
| Toronto (YTO) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 21, 2026 | Starting from CAD149 Seen: 3 hours ago |
| Toronto (YYZ) | Calgary (YYC) | One-way fare / Economy | Depart Apr 17, 2026 | Starting from CAD170 Seen: 4 hours ago |
| Toronto (YYZ) | Fort Lauderdale (FLL) | One-way fare / Economy | Depart Aug 24, 2026 | Starting from CAD206 Seen: 6 hours ago |
| Vancouver (YVR) | Toronto (YYZ) | One-way fare / Economy | Depart Jun 16, 2026 | Starting from CAD146 Seen: 1 hour ago |
| Toronto (YTO) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 25, 2026 | Starting from CAD111 Seen: 4 hours ago |
| Ottawa (YOW) | Fort Lauderdale (FLL) | One-way fare / Economy | Depart Apr 25, 2026 | Starting from CAD229 Seen: 4 hours ago |
| Ottawa (YOW) | Orlando (MCO) | One-way fare / Economy | Depart Jun 12, 2026 | Starting from CAD196 Seen: 4 hours ago |
| Ottawa (YOW) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 06, 2026 | Starting from CAD228 Seen: 7 hours ago |
| Halifax (YHZ) | Toronto (YTO) | One-way fare / Economy | Depart Apr 20, 2026 | Starting from CAD118 Seen: 1 hour ago |
| Toronto (YYZ) | Halifax (YHZ) | One-way fare / Economy | Depart Apr 09, 2026 | Starting from CAD124 Seen: 7 hours ago |
| Ottawa (YOW) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 21, 2026 | Starting from CAD228 Seen: 1 hour ago |
| Toronto (YYZ) | Orlando (MCO) | One-way fare / Economy | Depart Apr 07, 2026 | Starting from CAD214 Seen: 4 hours ago |
| Hamilton, CA (YHM) | Vancouver (YVR) | One-way fare / Economy | Depart Apr 15, 2026 | Starting from CAD149 Seen: 3 hours ago |
| Ottawa (YOW) | Calgary (YYC) | One-way fare / Economy | Depart Jun 25, 2026 | Starting from CAD208 Seen: 4 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 21, 2026 | Starting from CAD135 Seen: 4 hours ago |
| Vancouver (YVR) | Toronto (YTO) | One-way fare / Economy | Depart Apr 11, 2026 | Starting from CAD141 Seen: 3 hours ago |
| Halifax (YHZ) | Ottawa (YOW) | One-way fare / Economy | Depart Apr 30, 2026 | Starting from CAD222 Seen: 2 hours ago |
URL Parameter All to All - Mary