Cheap flights from Richmond to Chicago from $111

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 November is your next best option. Flight prices from Richmond to Chicago during November average around $369.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $445. 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 $553.

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 $458. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $482.

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 $423 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 5% on your flight if you consider stops on a Richmond to Chicago flight.

As of September 2026, prices for Richmond to Chicago flights are approximately 54% more expensive when compared to flights at the same time last year.

Southwest and Delta 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 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 22 flights per day flying from Richmond to Chicago. The most common time of day flights depart is 6:00AM, with 60% of flights taking off at noon.

As of September 2026, 159 flights take off from Richmond and land in Chicago each week. The most common flight departure day for this route is Sat, with 20% of weekly flights taking off on this day.