Day 1:
Chicago
To ensure your trip kicks off with a happy belly, stop at one of four Cafe Tola locations spread across the city. Enjoy the vibrant Mexican vibe, choose from a variety of breakfast tacos and burritos, and grab an authentic Cuban coffee to go as you embark on your adventure.
If you’re unfamiliar with the city or have no clue where to start, the Chicago Greeter program is a wonderful option. You’ll get a customized guided tour based on your choice of neighborhoods and interests, and you can even request a Spanish-speaking guide.
Those following their own agenda can head to the Art Institute of Chicago, which showcases a number of artworks from Aztec culture, including the Coronation Stone of Motecuhzoma II. If you have time, stop by the Field Museum to feast your eyes on Máximo (which translates to “maximum” or “most” in Spanish). It's the largest dinosaur ever discovered, living more than 100 million years ago in what is now Patagonia.
Also, take a trip to the National Museum of Puerto Rican Arts and Culture and explore a wealth of exhibits and attractions that celebrate the art and history of Puerto Rican culture. Be sure to check out the pop-up exhibit called Resistencia Y Libertá which honors the community expression of Afro-Puerto Rican Bomba music in fashion.
Take a break from your educational endeavors at Navy Pier, where you can sit down for a lunch of Latin-inspired cuisine at Lírica before checking out some of the Pier’s attractions. After that, pop over to the Magnificent Mile Plaza that houses the statue of Benito Juárez, and gaze up at the first and only indigenous President of Mexico.
To round out your Latin American history experience, travel up to the Newberry Library, where you’ll find plenty of fascinating materials directly related to the Aztec and Nahua people, Tenochtitlan, and more.
A modest walk of a few blocks will lead you to Tzuco, an imaginative French Mexican restaurant led by Chef Carlos Gaytán—the first Latin American to earn a Michelin Star. After relaxing over appetizers and drinks, meander through the brightly lit city streets to Jaleo for dinner, where you’ll experience Chef José Andrés and his creative take on rich Spanish cuisine.
If a big, delicious dinner hasn’t zapped your energy, stop by Cruz Blanca Cervecería in the West Loop for a tasty Mexican craft beer before calling it a night. Stay at the Wicker Park Inn, a charming Latina-owned bed and breakfast.