Cheap flights from Vermont to Chicago from $107

The month of September is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Vermont averaging around $334.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport 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. On the other hand, Sunday is the most expensive day to depart from Vermont because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $693.

Flying to Chicago O'Hare Intl Airport from Vermont in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $444 when looking at flights departing in the afternoon. Try not to purchase tickets in the morning because they tend to be around $502. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Vermont when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $374 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Vermont for as low as $248 on momondo.

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

As of August 2026, 23 flights take off from Vermont and land in Chicago O'Hare Intl Airport each day. The most common flight departure time for this route is 5:00AM, with 31% of daily flights taking off in the morning.

As of August 2026, there are 165 flights per week flying from Vermont to Chicago O'Hare Intl Airport. The most common day of the week flights depart is Mon, with 33% of flights taking off on this day.