Cheap flights from Chicago to San José del Cabo from $113

The cheapest month to fly to San José del Cabo from Chicago is in September. Flight prices, which tend to average around $486, are often lower during this time because this is during the off-season. If you’re not able to fly to San José del Cabo in September, then January is your next best option. Flight prices from Chicago to San José del Cabo during January average around $597.

According to our data, Tuesday is the cheapest day to fly to San José del Cabo from Chicago. The lowest ticket price found for a Tuesday departure recently was $633. 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, Thursday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $747.

Fly from Chicago O'Hare Intl to San José del Cabo Los Cabos for the best Chicago - San José del Cabo Los Cabos flight prices

You are more likely to see cheaper flights to San José del Cabo from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to San José del Cabo for around $640 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to San José del Cabo from Chicago for as low as $581 on momondo.

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

You could potentially save up to 19% on your flight if you consider stops on a Chicago to San José del Cabo flight.

Viva and Volaris are the most popular carriers operating from Chicago to San José del Cabo Los Cabos

American Airlines, United Airlines and Volaris are the top three most popular airlines that fly to San José del Cabo from Chicago according to our data. American Airlines is the first choice among our users, with 53% of people opting to fly with this airline when traveling to San José del Cabo. Keep in mind that there are 5 different airlines that fly to San José del Cabo on a routine basis, so you have a few additional options to choose from.

Mexico City (MEX) was the most common stop: 53% of momondo users choosing 1-stop flights on this route connected there.

Flights via Mexico City (MEX) offer the lowest average round-trip price of $318.

Flights connecting via Dallas (DFW) have the shortest average one-way travel time: 6h 59m.

Phoenix (PHX) has the shortest average layover time for this route: 1h 30m.

The number of flights available between Chicago and San José del Cabo is 3 per day as of November 2026. The most frequent departure time is 9:00AM, with 100% of daily flights leaving at noon.

21 flights are operational weekly from Chicago to San José del Cabo as of November 2026. The most popular departure day for this route is Mon, with 14% of flights per week taking off on this day.