3 DAYS IN CHICAGO windows, wood beams, balconies, and impeccable landscaping. Former President Barack Obama chose Chicago as the home of his Obama Presidential Center (opening in spring 2026) and its Home Court athletic and event center, opening in late 2025. Plans for the Jackson Park campus include a library, museum, John Lewis Plaza, and The Forum Building. Public gathering spaces include the Ann Dunham Water Garden honoring Obama’s mother, the Hadiya Pendleton Winter Garden, and the Elie Wiesel Auditorium. EVENING Choices abound for your last night of entertainment in Chicago. Make it a special evening by visiting one of these venues. A Rock & Roll Hall of Fame guitarist is behind the magic that happens Wednesday through Sunday nights at Buddy Guy’s Legends in the South Loop. Buy tickets in advance for your group to hear live blues music by some of the genre’s biggest artists while enjoying Southern fare like Louisiana-style gumbo. Be sure to check out the blues memorabilia that adorns the walls. Guy himself performs every January. In Lincoln Park, see performances on two stages at Kingston Mines , the oldest continuously operating blues club in Chicago. Some of the brightest stars in the business perform here Thursday through Sunday nights. Arrive early for the best seating. Doc’s Kitchen is open nightly, serving pub fare in addition to Southern specialties like catfish and pecan pie. Groove to jazz and big band beats in Uptown at the historic Green Mill , featuring live music every night. Open since 1907, it’s said to be the Buddy Guy's Legends country’s oldest jazz club and a former haunt of Prohibition Era gangsters. Your group can hit the dance floor when bands play dance music on Tuesday and Thursday evenings. The popular cocktail lounge accepts cash only and doesn’t take reservations. In Pilsen, catch a concert at Thalia Hall , where shows range from indie rock bands to singer-songwriters and DJs. The turn-of-the-century landmark’s architectural inspiration came from the Prague Opera House. Head down to the retro basement for a drink at Punch House or check out Tack Room , a cozy cocktail bar with a pianist and patio seating. Thalia Hall’s restaurant, Mariscos San Pedro , specializes in Mexican seafood. For artisanal cocktails made by expert mixologists, stop by The Violet Hour in Wicker Park. The cocktail menu changes with the season. There are three salons with candlelit tables, but the venue offers private areas for larger parties. For a fun group activity, book a dinner and cocktail-making class. Lincoln Park AFTERNOON For your afternoon adventure, choose to explore either the Latino culture of Pilsen or the Asian history of Chicago’s Chinatown. PILSEN In this culturally rich neighborhood, see outstanding artwork and exhibits celebrating Mexican heritage and history at the free National Museum of Mexican Art . Attend cultural events and programs highlighting visual and performing arts, including dance, music, theatre, and literature. View the vivid murals along lively 16th Street and nearby blocks at your own pace using A Guide to Pilen’s Murals , available on the National Museum of Mexican Art’s website. While strolling the neighborhood, stop by one of the authentic taquerias or bakeries. Next, peruse the galleries on South Halsted Street in the Chicago Arts District . End the afternoon at the Pilsen Arts & Community House , a nonprofit gallery curating local exhibitions and offering pop-up shows, artist talks, and art instruction. Its mission is to nurture creativity, culture, and community. Guided mural tours of the neighborhood are offered. CHINATOWN In Chinatown, make your first stop the Chinese American Museum of Chicago and delve into the neighborhood’s history with exhibits that range from art to military heroes, food, and storytelling. Book your group visit for a customized introduction to rich Chinese culture. Pause for photos at the iconic Chinatown Gate , then shop for souvenirs in the colorful boutiques or stop for a sweet from an authentic Chinese bakery or boba tea shop along Wentworth Avenue . In Chinatown Square , discover eateries offering dim sum and an array of Chinese cuisine. Look for the 12 bronze sculptures on the plaza that represent the animal signs of the Chinese zodiac. Along the Chicago River on a former railyard site, Ping Tom Memorial Park is a great place to relax, stroll waterfront paths, and enjoy views of the city skyline before your afternoon in Chinatown ends. You can also catch a seasonal Chicago Water Taxi here, an inexpensive way to whisk your group to and from downtown. TOP: @TEQUILAGRAPHICS 5
Chicago Travel Professionals Guide 2025: Page 5
