Flights to Chicago (ORD)
Looking for flights to Chicago? I track round-trips into Chicago, USA from 14 departure cities. Cheapest right now: US$234 from Miami. Cheap flights to Chicago change daily — click any route for price history and deal score.
| Route | Price | Airline | Dates | Stops | Savings |
|---|---|---|---|---|---|
| Miami → Chicago (ORD) | US$234 | Frontier | Oct 2026 | 1 | US$24 off |
| New York → Chicago (ORD) | US$237 | American | Dec 2026 | Non-stop | — |
| San Francisco → Chicago (ORD) | US$244 | Frontier | Oct 2026 | 1 | US$34 off |
| Los Angeles → Chicago (ORD) | US$247 | American | Oct 2026 | Non-stop | US$44 off |
| Calgary → Chicago (ORD) | $383 | United | Oct 2026 | Non-stop | $34 off |
| Montreal → Chicago (ORD) | $410 | Air Canada | Oct 2026 | Non-stop | $17 off |
| Toronto → Chicago (ORD) | $439 | Air Canada | Dec 2026 | 1 | $10 off |
| Halifax → Chicago (ORD) | $488 | Air Canada | Oct 2026 | 2 | $6 off |
| Vancouver → Chicago (ORD) | $492 | Air Canada | Dec 2026 | 1 | $4 off |
| Quebec City → Chicago (ORD) | $512 | Air Canada | Dec 2026 | 2 | $3 off |
| Edmonton → Chicago (ORD) | $552 | United | Oct 2026 | 1 | $142 off |
| Victoria → Chicago (ORD) | $558 | Air Canada | Oct 2026 | 1 | $127 off |
| Winnipeg → Chicago (ORD) | $622 | WestJet | Oct 2026 | 1 | $170 off |
| Ottawa → Chicago (ORD) | $649 | Porter Airlines | Dec 2026 | 1 | $42 off |