Cheap flights from Chicago to Sofia from $321

The cheapest month to fly to Sofia from Chicago is in February. Flight prices, which tend to average around $589, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of February, then book flights to Sofia from Chicago during January instead. Flights to Sofia in January, while not as cheap as those in February, still average around $620.

You are more likely to see cheaper flights to Sofia from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Sofia for around $831 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Sofia from Chicago for as low as $749 on momondo.

You could potentially save up to 16% on your flight if you consider stops on a Chicago to Sofia flight.

As of October 2026, prices for Chicago to Sofia flights are approximately 16% cheaper when compared to flights at the same time last year.

Turkish Airlines is the most popular carrier operating from Chicago to Sofia

Turkish Airlines, Lufthansa and LOT are the top three most popular airlines that fly to Sofia from Chicago according to our data. Turkish Airlines is the first choice among our users, with 33% of people opting to fly with this airline when traveling to Sofia. Keep in mind that there are 12 different airlines that fly to Sofia on a routine basis, so you have a few additional options to choose from.

Istanbul (IST) was the most common stop: 31% of momondo users choosing 1-stop flights on this route connected there.

Flights via London (LHR) offer the lowest average round-trip price of $641.

Flights connecting via Vienna (VIE) have the shortest average one-way travel time: 11h 52m.

Warsaw (WAW) has the shortest average layover time for this route: 1h 33m.