Cheap Flights from Toronto to Chicago
Looking for cheap flights from Toronto to Chicago? PointsYeah scans award availability across major airline and bank transfer programs in one place, so travelers can compare the lowest points and cash routes faster. Instead of searching each airline separately, users can see pricing from programs like Chase, Amex, Capital One, Citi, and Bilt side by side.
Award prices from Toronto to Chicago vary by season and date, but economy flights can start around 4,500–16,000 points one way, with premium cabins available at higher mileage levels. The live search above allows filtering by cabin, airline, stops, or maximum points to find the best award flights from Toronto to Chicago for specific travel dates.
2026-04-12
YYZ - ORD
Economy | Non stop
From 16,000 Pts + $62.9
2026-04-12
YYZ - ORD
Economy | Non stop | 4 left
From 4,500 Pts + $75.2
2026-04-13
YYZ - ORD
Economy | 1 Stop | 9+ left
From 12,500 Pts + $80.8
2026-04-13
YYZ - ORD
Economy | 1 Stop | 5 left
From 13,900 Pts + $68.7
2026-04-13
YYZ - ORD
Economy | 1 Stop
From 12,500 Pts + $68.5
2026-04-14
YYZ - ORD
Economy | Non stop
From 12,500 Pts + $62.9
Premium cabin flights from Toronto to Chicago
Premium cabin
2026-04-12
YYZ - ORD
First | Non stop | 1 left
From 30,000 Pts + $63
Premium cabin
2026-04-12
YYZ - ORD
Business | Non stop | 1 left
From 45,000 Pts + $63
Premium cabin
2026-04-12
YYZ - ORD
Business | Non stop
From 32,500 Pts + $62.9
Premium cabin
2026-04-12
YYZ - ORD
Business | Non stop | 6 left
From 9,000 Pts + $75.2
Premium cabin
2026-04-13
YYZ - ORD
Business | Non stop | 6 left
From 9,000 Pts + $75.2
Premium cabin
2026-04-13
YYZ - ORD
First | 1 Stop | 6 left
From 36,300 Pts + $68.7
Selected hotels for your next stay
Vernon Hills (United States)
Hotel Indigo Chicago-Vernon Hills
From 16,000 Pts or $115
Chicago (United States)
Thompson Chicago
From 17,000 Pts or $231
Chicago (United States)
Chicago Athletic Association
From 17,000 Pts or $314
Frequently Asked Questions
The cheapest route from Toronto to Chicago depends on award space, transfer bonuses, and travel dates. PointsYeah compares bank and airline programs in one place so you can find the best points and cash combinations faster.
Yes. Transferable points from Chase, Amex, Capital One, Citi, and Bilt can often be moved to airline partners for flights from Toronto to Chicago.
Yes. Searching metro codes when available helps compare nearby airport combinations for flights from Toronto to Chicago.
Our mission is to provide
the simplest and best
points travel planning
experience. Yeah!
Our mission is to provide the simplest and best
points travel planning experience. Yeah!
