Embark on a culinary and architectural journey in the Windy City

Beloved internationally for its towering Art Deco skyline and contributions to comedy and cuisine, Chicago is one the most cosmopolitan and diverse cities in North America. Chicago’s cultural neighborhoods include restaurants, museums and places of worship, and they are all excellent additions to any Chicago itinerary.

Greektown just west of the Loop is home to authentic Hellenic tavernas and bakeries that span generations of ownership. Orient yourself at the National Hellenic Museum, which explores millennia of Greek history and profiles the Greek immigrant experience through art exhibitions and priceless artifacts. For a group-friendly meal, visit Greek Islands, which simulates the Aegean coast with elaborate murals and serves fried zucchini chips, keftedakia meatballs and flambéed saganaki (fried cheese). Other local favorites that line Halsted Street include Athena, which offers delectable lunches on an expansive patio, and Artopolis, a multi-story bakery that specializes in galaktoboureko (a milk custard held in a phyllo shell).

Welcoming trattorias and cafes line Taylor Street—the primary artery for Chicago’s Little Italy. Learn about the city’s rich Catholic heritage as you admire the arched ceilings in the Shrine of Our Lady of Pompeii or massive dome at the Norte Dame de Chicago, and you can visit the nearby Jane Addams Hull House Museum to learn about the early American Progressive Movement. Of course, no visit to Little Italy is complete without a hearty meal, and you have dozens of options. Enjoy no-frills deli sandwiches at Conte de Savoia, small plates ideal for sharing at Davanti Enoteca or a wood-fired pizza at Pompeii.

Chicago’s Chinatown

Chicago’s Chinatown

Pass under a paifang archway and past the Nine Drago Wall to the heart of Chicago’s Chinatown. Begin at the Chinatown Square Mall, a pedestrian-friendly space that includes boutiques and cafes in addition to 12 zodiac statues and a massive mosaic comprised of 100,000 glass shards. Continue to Wentworth Avenue for a variety of tempting dining options, including dim sum at the Phoenix Restaurant, casual noodle dishes at Strings Ramen Shop and sweet coconut custard buns at Chiu Quon. Stop by the Chinese American Museum of Chicago, which chronicles the Midwestern Chinese immigrant experience with rotating exhibits that spotlight art and fashion.

Pilsen—located on the city’s southwest side—was originally a German immigrant neighborhood before transforming into a flourishing Hispanic community. The area’s most famous feature is its vibrant murals, from the colorful La Mujeres by Francisco Mendoza that covers the 18th Street Station to The Declaration of Immigration, a two-story mural by acclaimed artist Salvador Jimenez.

Learn more about these artists at the National Museum of Mexican Art, which provides curated tours for groups and a revolving series of artist showcases. Dining options include 5 Rabanitos (where you can sample spicy torta ahogada), Don Pedro Carnitas for savory tacos and Dusek’s for a craft cocktail.