Cheap flights from Vermont to Chicago from $65

The month of September is, on average, the cheapest month to fly to Chicago from Vermont, with most prices found around $279. If you’re not able to fly to Chicago in September, then October is your next best option. Flight prices from Vermont to Chicago during October average around $290.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $438. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Vermont to Chicago for around $652.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Vermont to Chicago during this time can be as low as $436. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $488.

Fly from Burlington to Chicago O'Hare Intl for the best Vermont - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Vermont when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $372 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Vermont for as low as $250 on momondo.

There are 4 cabin classes available to choose from on Vermont to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

The number of flights available between Vermont and Chicago is 34 per day as of February 2026. The most frequent departure time is 4:00PM, with 66% of daily flights leaving in the afternoon.

238 flights are operational weekly from Vermont to Chicago as of February 2026. The most popular departure day for this route is Mon, with 18% of flights per week taking off on this day.