Flights to Chicago (ORD)
Looking for flights to Chicago? I track round-trips into Chicago, USA from 14 departure cities. Cheapest right now: US$194 from Phoenix. Cheap flights to Chicago change daily — click any route for price history and deal score.
| Route | Price | Airline | Dates | Stops | Savings |
|---|---|---|---|---|---|
| Phoenix → Chicago (ORD) | US$194 | Frontier | Oct 2026 | Non-stop | US$99 off |
| Boston → Chicago (ORD) | US$215 | United | Oct 2026 | Non-stop | US$80 off |
| Washington DC → Chicago (ORD) | US$247 | Frontier | Oct 2026 | 1 | US$40 off |
| Miami → Chicago (ORD) | US$256 | Frontier | Oct 2026 | 1 | US$53 off |
| San Francisco → Chicago (ORD) | US$272 | Frontier | Oct 2026 | 1 | US$69 off |
| New York → Chicago (ORD) | US$307 | American | Oct 2026 | Non-stop | — |
| Seattle → Chicago (ORD) | US$317 | United | Oct 2026 | Non-stop | US$37 off |
| Calgary → Chicago (ORD) | $448 | WestJet | Oct 2026 | Non-stop | $96 off |
| Kelowna → Chicago (ORD) | $502 | WestJet | Oct 2026 | 1 | $104 off |
| Edmonton → Chicago (ORD) | $511 | WestJet | Oct 2026 | 1 | $76 off |
| Victoria → Chicago (ORD) | $522 | Air Canada | Oct 2026 | 1 | $266 off |
| Winnipeg → Chicago (ORD) | $530 | WestJet | Oct 2026 | 1 | $272 off |
| Regina → Chicago (ORD) | $532 | WestJet | Oct 2026 | 1 | $63 off |
| Quebec City → Chicago (ORD) | $624 | Air Canada | Dec 2026 | 1 | $50 off |