Cheap flights from Chicago to Vermont from $107

In general, October is the cheapest month to fly from Chicago to Vermont. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $130. The month of March is another great option to travel to Vermont, with average flight prices from Chicago averaging around $144.

The cheapest day to depart on your flight to Vermont is on a Wednesday when prices can be found for as low as $288. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Vermont is Friday, with ticket prices averaging around $386.

In the evening is the cheapest time of day to fly from Chicago to Vermont when you can find flight prices for as low as $319. Flying to Vermont in the evening is an ideal time because this is during off-peak travel hours. Try not to purchase tickets in the morning because they tend to be around $369. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Vermont from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Vermont for around $374 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Vermont from Chicago for as low as $220 on momondo.

As of May 2026, there are 58 flights per day flying from Chicago to Vermont. The most common time of day flights depart is 6:00PM, with 47% of flights taking off in the evening.

408 flights are operational weekly from Chicago to Vermont as of May 2026. The most popular departure day for this route is Mon, with 16% of flights per week taking off on this day.