$296 Find cheap flights from Chicago to Rutland

In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Rutland was $296 for a one-way ticket and $488 for a round-trip.

A passport is not required to fly from Chicago to Rutland.

We unfortunately don’t have that data for this specific route.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Rutland.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Rutland from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Rutland with an airline and back to Chicago with another airline. Booking your flights between Chicago and RUT can sometimes prove cheaper using this method.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Rutland from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.