Cheap flights from Virginia to Chicago from $107

The month of January is, on average, the cheapest month to fly to Chicago from Virginia, with most prices found around $351. If you’re not able to fly to Chicago in January, then February is your next best option. Flight prices from Virginia to Chicago during February average around $358.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $473. 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 Virginia to Chicago for around $622.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Virginia to Chicago during this time can be as low as $475. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $529.

Fly from Staunton Shenandoah Valley to Chicago O'Hare Intl for the best Virginia - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Virginia when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $417 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Virginia for as low as $340 on momondo.

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

Frontier, United Airlines, and Delta are the most popular carriers operating from Virginia to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Virginia according to our data. United Airlines is the first choice among our users, with 54% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 6 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of September 2026, there are 33 flights per day flying from Virginia to Chicago. The most common time of day flights depart is 5:00PM, with 45% of flights taking off at noon.

The number of flights available between Virginia and Chicago is 232 per week as of September 2026. The most frequent departure day is Wed, with 30% of weekly flights leaving on this day.