Find cheap flights to Chicago from CA$139
Trusted by millions
Kiwi.com Guarantee for stress-free travel
One search, all the best deals
Explore deals for your Chicago getaway
Prices updated:
Prices updated:
Weather in Chicago
Average Weather
| Month | Average monthly max temperature | Average monthly min temperature |
| January | -1°C | -6°C |
| February | 0°C | -5°C |
| March | 6°C | 0°C |
| April | 11°C | 4°C |
| May | 17°C | 10°C |
| June | 22°C | 16°C |
| July | 25°C | 20°C |
| August | 25°C | 19°C |
| September | 22°C | 16°C |
| October | 15°C | 10°C |
| November | 8°C | 3°C |
| December | 2°C | -1°C |
14 day forecast
Cheapest month to fly to Chicago
Explore price trends for trips to Chicago
Showing prices in CAD
| Annual Avg. Price | 185 CAD |
| August 2025 | 131 CAD |
| September 2025 | 124 CAD |
| October 2025 | 127 CAD |
| November 2025 | 145 CAD |
| December 2025 | 203 CAD |
| January 2026 | 150 CAD |
| February 2026 | 124 CAD |
| March 2026 | 231 CAD |
| April 2026 | 242 CAD |
| May 2026 | 230 CAD |
| June 2026 | 329 CAD |
Direct flights to Chicago
Find direct flights from anywhere to Chicago
- Ottawa to Chicago from CA$313
- Guadalajara to Chicago from CA$332
- Calgary to Chicago from CA$348
- Edmonton to Chicago from CA$402
- Winnipeg to Chicago from CA$410
- Halifax to Chicago from CA$553
- New Delhi to Chicago from CA$826
- Zürich to Chicago from CA$922
- Vienna to Chicago from CA$1,104
- Copenhagen to Chicago from CA$1,163
- Barcelona to Chicago from CA$1,251
- Paris to Chicago from CA$1,520
Airlines flying to Chicago
Best airlines flying to Chicago
- ITA Airways
- Jin Air
- Austrian Airlines
- Condor
- EVA Air
- All Nippon Airways
- Jetstar Airways
- Iberia Airlines
- IndiGo Airlines
- JetBlue Airways
- Tunisair
- Fiji Airways
- Tway Airlines
- Finnair
- Ethiopian Airlines
- Air Canada
- French Bee
- TAP Portugal
- Air Transat
- Qantas
