Flights to Chicago
Chicago has the best architecture in North America and a lakefront that runs for 30 kilometres. O'Hare is one of the world's busiest airports, making it a reliable connecting point for US domestic routes.
Cheapest flights to Chicago
Lowest return fares we've found, by departure city.
| From | Lowest fare | Nonstop | |
|---|---|---|---|
| Amsterdam (AMS) | $486 | — | View fares |
When to fly to Chicago
May to October. Winter on the lake is genuinely severe — wind chill regularly drops below -20°C.
Fares to Chicago move with season and demand. Each route page above shows month-by-month prices for that specific city pair, which is a far better guide than a general rule of thumb.
Flights to Chicago: common questions
How much does it cost to fly to Chicago?
The cheapest return fare we've recorded is $486 from Amsterdam. Fares from other cities are listed above.
What is the best time to visit Chicago?
May to October. Winter on the lake is genuinely severe — wind chill regularly drops below -20°C.
Which airports serve Chicago?
Chicago is served by Merrill C Meigs (CGX), DuPage Airport (DPA), Chicago Midway International Airport (MDW), O'Hare International Airport (ORD), Chicago Executive Airport (PWK), Chicago Rockford International Airport (RFD).
How far in advance should I book flights to Chicago?
For long-haul routes, 2–5 months ahead usually gives the best fares; short-haul is typically cheapest 3–8 weeks out. Each route page shows that route's own price pattern by month.