Flying to Chicago rewards the traveller who books early and stays flexible. Domestic fares from the East Coast are often under $120, while transatlantic routes from London or Frankfurt tend to be competitive in shoulder season. O'Hare suits frequent flyers who know its quirks; Midway is the smarter choice for budget carriers. Best suited to city-break enthusiasts, architecture obsessives, and anyone who takes food seriously.
What works well
- World-class food
- Huge flight choice
- Great BNPL coverage
What to watch
- Book early Dec-Jan
- O'Hare can delay
January fares dip to $89, but that's Lake Michigan wind chill you're buying into, so weigh the saving against the scarf budget. O'Hare's Terminal 5 customs hall can eat 45 to 75 minutes on busy days, and anything under a 60-minute connection is a gamble not worth taking. The neon underground walkway between Terminals 1, 2, and 3 is the one part of the airport worth savouring rather than rushing. Klarna, Afterpay, Affirm, and Sezzle all clear at checkout with instant approval, which is more than can be said for O'Hare's timetable in July.





