Skyline photo of Chicago

MasterClass Executive Explore Chicago

Things to Do While in Chicago

We hope you enjoy our city as much as we do. If you have time during your visit, we invite you to explore some of our favorite places and experiences around Chicago.
[ Transportation Options ]

Full shot of Harper center building

University of Chicago (Hyde Park)

Explore the Charles M. Harper Center

Food

  • Medici on 57th—the classic UChicago hangout, known for pizza, burgers, and rooftop dining. A rite of passage.
  • Valois—no-frills cafeteria-style spot on 53rd Street, famous as one of Obama's regular breakfast stops when he taught at the law school.
  • Virtue Restaurant—upscale Southern cuisine and a two-time James Beard Award winner; great for a nicer dinner.
  • Plein Air Café—cozy French-inspired café right next to Robie House, good for coffee or a light breakfast/lunch.

Art

  • Smart Museum of Art—a free museum on campus showcasing works by Rembrandt, Picasso, and contemporary artists, with a lovely sculpture garden.
  • The Renaissance Society—one of the oldest contemporary art museums in the country, located on campus, known for cutting-edge exhibitions.
  • Hyde Park Art Center—contemporary work by Chicago-area artists, with a more community/gallery feel than the campus museums.

History

  • Robie House—a Frank Lloyd Wright masterpiece and UNESCO World Heritage Site, considered one of the most important buildings of the 20th century.
  • Rockefeller Memorial Chapel—campus landmark highlighting soaring Gothic architecture with striking stained glass.
  • Obama Presidential Center—opened in June 2026, the grounds are free and open daily. Include a public library branch, an NBA-regulation basketball facility, gardens, and a playground, alongside the ticketed museum.
  • Griffin Museum of Science and Industry—a historic museum and landmark that dates back to the 1893 World’s Fair.
University of Chicago (Hyde Park)
River view of Gleacher Building

Downtown Chicago (Gleacher)

Explore the Gleacher Center

Food

Entertainment

  • Millennium Park — a public park in downtown Chicago, best known for the "Cloud Gate" bean sculpture and free year-round programming along the lakefront.
  • Magnificent Mile — a prime retail, dining, and entertainment destination located on a mile-long stretch of Chicago’s Michigan Avenue.
  • The Art Institute of Chicago — a world-renowned art museum that is home to more than 300,000 pieces of art. Tickets required.
  • Field Museum — a natural history museum located in Grant Park with rotating special exhibits such as the Pokémon Fossil Museum. Tickets required.
  • Architecture Boat Tour — several companies offer boat tours along the Chicago River, providing passengers with up-close views of landmark buildings and historic facts about the city. Tickets required.
  • Winter’s Jazz Club — Chicago’s top spot for local and national live jazz music. Tickets required.
Downtown Chicago (Gleacher)

Transportation

For travel between Airports and Downtown:

O’Hare International Airport (ORD):

  • CTA Blue Line: Runs directly from O'Hare to downtown with no transfers, taking you straight to Clark & Lake in the Loop. Runs 24/7, with trains every 15–30 minutes overnight, so it's a solid choice even for late arrivals. Fare is $5 for trips originating at O'Hare.
  • Rideshare/Taxi: Typically, $50–$70 to downtown, roughly 30–45 minutes depending on traffic.

From Midway (MDW):

  • CTA Orange Line: Station is connected directly to the terminal — just follow signs, no need to go outside. Fare is $2.50, and it reaches the Loop in under 30 minutes. Note: The Orange Line stops running around 1:00 AM, so after that you'd need the N62 Archer bus, which runs 24 hours.
  • Rideshare/Taxi: Typically, $25–$40, 20–45 minutes depending on traffic.

For travel between Downtown and Hyde Park:

  • Metra Electric Line: Fastest and most reliable option. Board at Millennium Station (near Michigan Ave/Randolph) and get off at the 59th St station. Ride is about 15–20 minutes. Trains run frequently on weekdays, but it's worth checking the schedule ahead. Day passes begin at $7.50.
  • CTA Bus: The #6 Jackson Park Express runs from downtown (State Street) straight to Hyde Park, no transfers needed. Takes about 30–40 minutes depending on traffic. Three-day passes are $15.
  • Rideshare / Taxi: Easiest door-to-door option, especially with luggage or on a tight schedule. Typically, 15–25 minutes depending on traffic, longer during rush hour. Typically, $30-50.