With both cities being served by several airports, it is very easy to find cheap flights from Los Angeles to Chicago. Although the direct flights are quite cheap, in some cases it’s cheaper to take an indirect flight (that’s if you don’t mind staying in airports).

Airport choices

When flying into Chicago, you’ll most likely land on Chicago O’Hare International Airport, although there are several other airports serving the city. O’Hare is located just 17 miles from downtown Chicago and serves as the largest hub for United Airlines and second largest hub for American Airlines. It is one of the busiest airports in the States, so finding flights to Chicago from any large American city is very easy. Midway International Airport is located 10 miles south of downtown and is hub for Southwest Airlines. Compared to O’Hare, Midway is sometimes a cheaper alternative.

When you need to fly out of Los Angeles, there are several airports to choose from. The biggest one is Los Angeles International Airport (LAX) and is located about 16 miles from downtown. The airport is a hub for United Airlines and a focus city for American Airlines, Delta Air Lines and Alaska Airlines. The other airports serving Los Angeles are small and not that busy but LAX is often the cheapest.

Best airline choices

The following airlines offer direct flights from Los Angeles to Chicago:

  • American Airlines
  • United Airlines
  • Southwest Airlines
  • US Airways
  • JetBlue Airways


If you fly from LAX to O’Hare, the cheapest airlines are American and United, while if you fly from LAX to Midway the cheapest option is Southwest Airlines.

Indirect flights are also available and sometimes they turn out to be cheaper than the direct flight. Of course, this option is possible if you don’t mind waiting in airports.

Typical prices

The airfare depends on when you fly and when you book your flight. It’s always a good idea to book in advance if you plan to save some money. Also, booking an indirect flight turns out to be cheaper than booking a direct flight (but only in some cases).

Typically, as the off season draws by the airfare starts going down but don’t expect very low fares. During the peak summer months and during the holidays, the prices are always higher.

If you book a direct flight during the off season (fall), expect to pay about $258 for a round trip flight. If you choose an indirect flight –via Dallas- you will pay only $194 for a round trip during the same time period.

Money saving tips

You could start your search by looking at discount websites such as Hotwire, Expedia, Travelocity and Priceline, which make it very easy to compare the fares.

If you don’t mind staying in airports, look for indirect flights from Los Angeles to Chicago. In many cases they turn out to be cheaper than the direct flight.

It’s always a good idea to be flexible. Flying mid-week usually saves some money.

Book your ticket in advance. Typically the cheapest fares can be found if you book 2 to 8 weeks before departure. If you book too close to your departure date the fares will be much higher although it’s possible to find last minute deals in some cases.