Flights from Chicago to Guadalajara offer a captivating journey that transports travelers from the heart of the Midwest to the vibrant heartland of Mexico. flights to guadalajara from chicago ? Departing from Chicago, a city renowned for its iconic skyline, cultural diversity, and rich history, you embark on a voyage spanning over 1,500 miles to Guadalajara, a city steeped in tradition yet pulsating with contemporary energy.