Morning: Check‑in at the Ameristar Casino Hotel in Gary, Indiana, and enjoy a leisurely breakfast at the hotel’s Café del Mundo. After settling in, try a few slot machines or the table games for a quick taste of the casino atmosphere.
Afternoon: Drive the short 30‑minute stretch to downtown Chicago and wander through Millennium Park, where the iconic “Bean” sculpture and Crown Fountain offer great photo ops. A short walk brings you to the Art Institute of Chicago, home to masterpieces like Seurat’s “A Sunday on La Grande Jatte.”
Evening: Dine at the beloved Chicago deep‑dish spot Lou Malnati’s for an authentic pizza experience, then take a sunset stroll along the Chicago Riverwalk. Return to the Ameristar for a nightcap at the casino’s bar or catch live music in the lounge.
Find HotelsMorning: Start with a hearty brunch at Portillo’s, famous for its Italian beef and chocolate cake. Then head to the soaring heights of Willis Tower Skydeck for breathtaking city views from the Ledge.
Afternoon: Explore the bustling attractions of Navy Pier, including the Ferris wheel, Chicago Children’s Museum, and lakeside promenade. Grab a quick lunch at the pier’s Giordano’s for a classic stuffed‑crust pizza.
Evening: Treat yourself to a memorable dinner at the trendy Girl & The Goat in the West Loop, then wander the vibrant streets of West Loop’s Fulton Market for a nightcap or dessert before heading back to Gary.
Find HotelsIf you have an extra day, consider adding a visit to the Field Museum or taking a scenic drive to the nearby Indiana Dunes State Park for beachside relaxation. To shorten the itinerary, skip the Willis Tower and replace the Girl & The Goat dinner with a quicker bite at a local hot‑dog stand, saving both time and money while still enjoying Chicago’s signature flavors.