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March Madness in Chicago is exciting, with events and activities that make the city come alive. While March Madness might bring basketball to mind, it is also a playful nod to the city’s unique traditions, like dyeing the Chicago River and hosting sporting events like the Men’s Big Ten Tournament.
While the tournament will skip Chicago in 2025, it will return in 2026. Book a room at Hilton Grand Vacations Club Magnificent Mile. I stayed there as an owner, but you can also book as a regular hotel guest. If you are driving, parking at the hotel is $62 per night with in/out privileges. For a cheaper option, try the PARK lot across the street (note: you will need to pay again if you leave). Apps like ParkChicago and SpotHero are lifesavers for street parking or discounted garage spaces nearby. Plan your parking before arrival to save time and money. If you want to watch a basketball game, head to the United Center to catch a Chicago Bulls game.
The staff greeted me with a smile, a bottle of water, and a warm DoubleTree chocolate chip cookie. The room featured an area rug instead of carpeting (great for allergy-sensitive guests), a large TV, and a cozy seating area near the window. While housekeeping was only available for stays longer than five days, the SMS concierge regularly checked in to ensure I had everything I needed. Are you a Massage Envy member? There is a location across the street from the DoubleTree. Make an appointment to unwind after a day of exploring.
I dined at HotHouse, located on the ground floor of the hotel. My server was friendly and quick to get the bartender when I had questions about cocktails. I tried the Como La Flor cocktail and Tiramisu Cake—both were exceptional. For dinner, I ordered buffalo wings to go. The cocktail was well-crafted, the tiramisu melted in my mouth, and the wings were flavorful, served with fresh celery and carrot sticks. If you are a Hilton Honors Amex cardholder, charge your meals to your room to rack up points.
Head to Timothy O’Toole’s, especially during Big Ten Weekend. Fans watched the games on big-screen TVs. I enjoyed a burger, fries, and a beer from the Happy Hour menu. Do not skip the pretzel bread pudding—it is shareable and delicious. As a member of the Hilton Honors Dining program, I earned bonus points for dining here. After each visit, leave a review to keep earning points. It is an easy way to make your routine meals more rewarding.
March in Chicago is not just about hoops. The dyeing of the Chicago River for St. Patrick’s Day is a must-see. Follow the crowds to find a good viewing spot, but expect long lines at nearby restaurants. If you stick around until late March, you can witness Chicagohenge, a natural alignment where the rising or setting sun perfectly frames Chicago’s east-west streets.
March is a fantastic time to experience Chicago’s unique blend of sports, culture, and seasonal wonders. Whether you are here for basketball, St. Patrick’s Day, or Chicagohenge, the Hilton Grand Vacations Club Magnificent Mile makes for a perfect home base. Do not forget to bring your running shoes. I purchased a pair on Amazon.
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