$135 Cheap United flights Chicago (ORD) to Monterey (MRY)

Grab cheap round-trip United Airlines flights from $269 from ORD to MRY by organizing your results from "Price (lowest to highest)" on Expedia. Or look for deals from $135 for a one-way trip.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for cheap United Airlines flights from O'Hare Intl. Airport (ORD) to Monterey Peninsula Airport (MRY) one to three months ahead of your day of departure. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and itinerary, the ideal day to book a domestic flight is usually Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC's global airline sales database.

Browse United Airlines's earliest flights from ORD to MRY by checking our "Morning" and "Early Morning" filters. Not only will you arrive at your destination sooner, early departures are also 20% less likely to be canceled.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.

Offering a rewarding loyalty program, United Airlines is a top choice for many passengers flying from ORD to MRY. Plus, as a United Mileage Plus and One Key™ member booking through Expedia, you could earn OneKeyCash™* on eligible flights on top of your airline miles.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.