Cheap flights from Baltimore to Chicago from $99

The month of September is, on average, the cheapest month to fly to Chicago Midway Airport from Baltimore, with most prices found around $171. If you are unable to visit Chicago Midway Airport during the month of September, then departing from Baltimore during the month November is also very affordable. Most momondo users find prices during this month for around $188.

According to our data, Saturday is the cheapest day to fly to Chicago Midway Airport from Baltimore. The lowest ticket price found for a Saturday departure recently was $334. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Baltimore because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $416.

Flying to Chicago Midway Airport from Baltimore at noon is the least expensive time of day to depart. momondo users have found prices as low as $321 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $378. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from Baltimore/Washington to Chicago Midway for the best Baltimore/Washington - Chicago Midway flight prices

You are more likely to see cheaper flights to Chicago Midway Airport from Baltimore when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $294 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Baltimore for as low as $224 on momondo.

There are 2 cabin classes available to choose from on Baltimore to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

No. A direct flight is the cheapest option for a flight between Baltimore to Chicago Midway Airport.

As of July 2026, prices for Baltimore to Chicago Midway Airport flights are approximately 9% more expensive when compared to flights at the same time last year.

Southwest and Delta are the most popular carriers operating from Baltimore/Washington to Chicago Midway

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Baltimore according to our data. Southwest is the first choice among our users, with 73% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

Historically, on average around 20% 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 122 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.

Wednesday is statistically the day of the week which experiences the fewest number of delays on this flight route. Friday 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 19% of their flights experiencing any sort of delay.

9 flights are operational daily from Baltimore to Chicago Midway Airport as of July 2026. The most popular departure time for this route is 5:00PM, with 56% of flights per day taking off in the afternoon.

The number of flights available between Baltimore and Chicago Midway Airport is 67 per week as of July 2026. The most frequent departure day is Sun, with 22% of weekly flights leaving on this day.