Find cheap flights from Chicago to Cabo San Lucas - Compare and Save

When flying out of Chicago you’ll be using one of these airports: Chicago Midway or Chicago O'Hare Intl. Cabo San Lucas does not have its own airport so you’ll be flying into nearby San José del Cabo Los Cabos airport, which is 21.7 mi away.

Direct flights cover the 1,813 miles separating Chicago and Cabo San Lucas in about 4h 49m.

3 direct flights run between Chicago and Cabo San Lucas on a daily basis. On average, there are about 21 departures each week.

Consider leaving on a Saturday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Fridays.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Cabo San Lucas.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cabo San Lucas from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Cabo San Lucas with an airline and back to Chicago with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Cabo San Lucas from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

In the last 5 days, the cheapest one-way ticket between Chicago and Cabo San Lucas found on KAYAK was with Volaris for $119. Volaris offered a round-trip connection from $207 and Viva from $223.