Our data shows that January tends to be the cheapest month to fly to Cabo San Lucas from Chicago Midway Airport. Users have commonly found prices around $506 for the month, but tickets can be as low as $294. Due to multiple factors, prepare for potentially higher prices in June.
To save on the cost of your flight from Chicago Midway Airport to Cabo San Lucas, book at least 61 days before your planned departure. Booking around this time can save you about 9% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $539 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $557.
When flying from Chicago Midway Airport to Cabo San Lucas, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.