Planning a trip to Chicago? Whether you’re here for business, a special event, or a weekend getaway, the Windy City offers endless attractions—iconic sights, world-class dining, and unforgettable experiences. But Chicago’s traffic, unpredictable weather, and parking challenges can quickly turn excitement into frustration. That’s where Pontarelli’s chauffeured transportation comes in, making every adventure smooth, safe, and stress-free.
Here are the top ten things to do in Chicago that are even better when you leave the driving to the professionals:
Start your Chicago journey at Navy Pier, a must-see for first-time visitors. Enjoy the Centennial Wheel, public art, and lakefront cruises. With Pontarelli, you’ll get dropped off right at the entrance—no parking headaches, just pure fun.
The Magnificent Mile is Chicago’s premier shopping destination, lined with luxury boutiques and flagship stores. Book a chauffeured car to keep your hands free and your day hassle-free.
Seeing the Chicago Cubs at Wrigley Field is a bucket-list experience. Avoid crowded trains and expensive parking—arrive like a VIP with Pontarelli and get picked up steps from the stadium after the game.
From the Art Institute of Chicago to the Field Museum and Shedd Aquarium, the city’s museums are world-famous. Make it a museum day and let your chauffeur handle city traffic and parking, so you can focus on the exhibits.
Chicago’s downtown Theatre District is home to Broadway shows, concerts, and comedy. With chauffeured transportation, you’ll never worry about running late or walking blocks in heels—just step out at the marquee and enjoy the show.
The Riverwalk is packed with trendy restaurants, bars, and unbeatable skyline views. Indulge in the city’s food scene and nightlife, knowing your private car is waiting whenever you’re ready to head to your next spot.
Chicago’s architecture is legendary. Book a private tour and let Pontarelli handle the logistics, so you can hop between historic sites and hidden gems without missing a beat.
Perfect for families and groups, Lincoln Park Zoo is free and open year-round. Skip the crowded parking lots and enjoy a smooth ride to and from the zoo with Pontarelli’s spacious vans or mini coaches.
From Lollapalooza to Taste of Chicago, the city’s festivals are not to be missed. Traffic and parking can be overwhelming during big events—let Pontarelli handle it, so you can focus on making memories.
Whether you’re attending a wedding at The Drake or a gala at the Art Institute, chauffeured transportation ensures you and your group arrive on time and in style. Pontarelli’s fleet includes luxury sedans, SUVs, and even vintage trolleys for a unique Chicago touch.
Why Book Chauffeured Transportation in Chicago?
Ready to Explore Chicago the Easy Way?
Since 1977, Pontarelli has provided luxury chauffeured transportation for visitors and locals alike. Whether you need airport transfers, event shuttles, or a private tour, our team is here 24/7 to make your Chicago experience unforgettable.
Book your ride today and discover why Pontarelli is Chicago’s trusted transportation partner.
Looking for more Chicago travel tips or want to customize your itinerary? Contact Pontarelli at info@pontarellischicago.com or call 312-361-4111. Your next adventure awaits!
Posted on Aug 8th 2025 by Pontarelli Chicago Limousine Service
