Cheap flights from Richmond to Chicago from $89

The month of February is, on average, the cheapest month to fly to Chicago from Richmond, with most prices found around $288. If you’re not able to fly to Chicago in February, then March is your next best option. Flight prices from Richmond to Chicago during March average around $381.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $469. 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 Richmond to Chicago for around $558.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Richmond to Chicago during this time can be as low as $456. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $499.

Fly from Richmond Byrd Intl to Chicago Midway for the best Richmond Byrd Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Richmond when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $426 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Richmond for as low as $348 on momondo.

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

You could potentially save up to 25% on your flight if you consider stops on a Richmond to Chicago flight.

As of October 2026, prices for Richmond to Chicago flights are approximately 13% cheaper when compared to flights at the same time last year.

Southwest, Frontier, and United Airlines are the most popular carriers operating from Richmond Byrd Intl to Chicago

United Airlines, American Airlines and Southwest are the top three most popular airlines that fly to Chicago from Richmond according to our data. United Airlines is the first choice among our users, with 55% 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 October 2026, there are 24 flights per day flying from Richmond to Chicago. The most common time of day flights depart is 5:00PM, with 61% of flights taking off at noon.

As of October 2026, 172 flights take off from Richmond and land in Chicago each week. The most common flight departure day for this route is Mon, with 19% of weekly flights taking off on this day.