Whether you want to visit Chicago for its music scene, shopping or dining opportunities, beaches or superb architecture, you will need to find a cheap flight from San Francisco. Luckily, with both cities being served by more than one airport, it’s easy to find a good deal, no matter when you plan to fly. However, you might want to consider Chicago’s climate before you plan your trip. Typically, May and September are mild and fine, while June can be a nice month to explore the outdoors.

Airport choices

Most visitors choose to land on Chicago O’Hare International Airport, although there are several other airports serving the city. O’Hare, the busiest airport serving Chicago, is located just 17 miles from downtown and serves as the largest hub for United Airlines and second largest hub for American Airlines. Midway International Airport is located 10 miles south of downtown and serves as hub for Southwest Airlines. In some cases it’s cheaper to fly into Midway than into O’Hare.

San Francisco area is served by several airports. The busiest and largest of them is San Francisco International Airport (SFO). The airport is located about 13 miles from the city center and serves as major hub for both United Airlines and Virgin America. Other airports in the area include Oakland International, which receives flights from other cities in the States and Mexico.

Best airline choices

Direct flights from San Francisco to Chicago are offered by United Airlines and American Airlines. Indirect flights are also offered by the following carriers:

  • Frontier Airlines
  • Delta
  • Northwest
  • Continental


Contrary to what seems logical, indirect flights aren’t always more expensive than direct flights. In this case, it might be cheaper to fly via Denver on Frontier Airlines than to take a direct flight on United Airlines.

Typical prices

It is a bit hard to draw conclusions about typical prices for flights from San Francisco to Chicago. The fares don’t change much from month to month but they tend to be higher during the peak tourist season (summer, winter holidays and national holidays). Also, choosing an indirect flight doesn’t necessarily mean that you’ll be paying more than if you choose a direct flight.

For example, if you need to fly in September, the fares range between $158 for a round trip indirect flight (via Denver) on Frontier Airlines and $197 for a round trip direct flight on American or United. Flying four weeks later doesn’t change the fares.

Money saving tips

It is a good idea to start the search by looking at discount websites such as Hotwire, Travelocity, Expedia, and Priceline. They make it easy to compare the fares and hence choose the best one for you.

If your approach is flexible then you have more chances to find a cheap flight. Flying mid-week is a good trick to secure a cheaper ticket. Avoid flying during the peak travel season. Typically, April, May, June and September are nice months to visit Chicago and they are outside the peak season, so the fares are lower.

If you don’t mind spending time in airports, it might be cheaper to choose an indirect flight rather than a direct one.

Of course, it’s always important to book your ticket in advance. Generally, the cheapest fares can be found if you book 2 to 8 weeks before departure. However, in some cases, even if you book too close to your departure date the fares might be quite affordable due to last minute offers. But you shouldn’t relay on luck.