Cheap flights from Rochester to Chicago from $88

The month of September is, on average, the cheapest month to fly to Chicago from Rochester, with most prices found around $334. If you’re not able to fly to Chicago in September, then August is your next best option. Flight prices from Rochester to Chicago during August average around $362.

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $426. 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 Rochester to Chicago for around $545.

Our most recent data shows that the best time of day to fly to Chicago is in the afternoon. Flights from Rochester to Chicago during this time can be as low as $424. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $497.

Fly from Greater Rochester Intl to Chicago Midway for the best Greater Rochester Intl - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Rochester when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $418 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Rochester for as low as $274 on momondo.

There are 4 cabin classes available to choose from on Greater Rochester Intl 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 16% on your flight if you consider stops on a Rochester to Chicago flight.

As of April 2026, prices for Rochester to Chicago flights are approximately 109% more expensive when compared to flights at the same time last year.

Delta and Southwest are the most popular carriers operating from Greater Rochester Intl to Chicago

American Airlines, United Airlines and Southwest are the top three most popular airlines that fly to Chicago from Rochester according to our data. American 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 5 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

As of April 2026, there are 26 flights per day flying from Rochester to Chicago. The most common time of day flights depart is 6:00AM, with 52% of flights taking off at noon.

184 flights are operational weekly from Rochester to Chicago as of April 2026. The most popular departure day for this route is Thu, with 17% of flights per week taking off on this day.