Cheap flights from Baltimore to Chicago from $65

The month of September is, on average, the cheapest month to fly to Chicago from Baltimore, with most prices found around $161. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Baltimore to Chicago during January average around $171.

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $382. 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 Baltimore to Chicago for around $505.

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Baltimore to Chicago during this time can be as low as $365. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $421.

Fly from Baltimore/Washington to Chicago O'Hare Intl for the best Baltimore/Washington - Chicago flight prices

You are more likely to see cheaper flights to Chicago from Baltimore when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $275 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Baltimore for as low as $184 on momondo.

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

Southwest and United Airlines are the most popular carriers operating from Baltimore/Washington to Chicago

United Airlines, American Airlines and Frontier are the top three most popular airlines that fly to Chicago from Baltimore according to our data. United Airlines is the first choice among our users, with 47% 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.

Historically, on average around 18% of flights between Baltimore and Chicago have experienced a delay on any given week. The average delay length over the past 12 months has been 120 minutes.

Generally, flights departing in the morning tend to experience fewer delays. Flights at night have, in the past, seen delays more frequently in comparison.

Saturday is statistically the day of the week which experiences the fewest number of delays on this flight route. Sunday has historically seen more delays on average compared to the rest of the week.

According to our data, Southwest have had the least number of delays on this route over the last 12 months; with about 18% of their flights experiencing any sort of delay.

As of February 2026, 18 flights take off from Baltimore and land in Chicago each day. The most common flight departure time for this route is 6:00AM, with 48% of daily flights taking off at noon.

As of February 2026, there are 131 flights per week flying from Baltimore to Chicago. The most common day of the week flights depart is Fri, with 20% of flights taking off on this day.