How To Become An Expert About Chicago

1. Wendella Tours & Cruises

The exploration begins at Wendella Tours & Cruises, which offers a variety of rides on both the river and Lake Michigan. One of the most “touristy” activities in the city, the 45-minute architecture tour is the perfect way to learn about Chicago’s background, with the added excitement of a scenic boat ride. Plus, it’s just fun to play tourist (if, that is, you’re a local).

Boarding for the tour is at the river level, so you’ll need to walk down a set of stairs (or a ramp) by the Wrigley Building off Michigan Avenue. The tours depart from two different docks, so check to make sure you have the correct one. Arrive at least 15 minutes early to queue up and watch the busy traffic on the river.

When your boat docks, you’ll board and listen to a brief safety overview. Passengers can choose from benches, chairs and standing-room spots but are also free to move around during the tour. Once everyone is situated, you’re off!

As you head east toward the lake, you’ll get up close to Navy Pier and other prominent attractions. It’ll be hard not to be awed by the views of downtown as well as the open water in front of you.

The tour continues back on the river, and you’ll weave under bridges, past skyscrapers and around condominiums. You’ll pass commuters making their way to the train, tourists meandering down Michigan Avenue, and diners enjoying a meal on the Riverwalk. The ride goes through the financial district, past the Merchandise Mart, along the Civic Opera House, and down to Chinatown and back.

Wave to the other tour boats, kayaks, and party pontoons you pass along the route — more often than not, they’ll wave back, sometimes initiating, too.

Don’t forget that your activity is more than just a ride on the river. As an architecture tour, the docent offers a broader wealth of information, teaching you fun facts about the city’s history, design and founders. Plus, you’ll be delighted to find out the word “Chicago” loosely translates to “stinky onion.”

Don’t forget to look upward at the Willis Tower, the tallest building in the world from 1973–1998. Remember that any self-respecting Chicagoan will always refer to it as the Sears Tower (its 2009 name change be damned).

Things to note:

– Tickets can be purchased in advance, which is a good idea on a busy day.
– Seating is first come, first served on the spacious top deck, and covered lower level. The boats are outfitted with bathrooms and offer concessions with drinks and light snacks.

2. Sweet Home Gelato

After all that time in the sun, everyone is ready for some sustenance. The Riverwalk is lined with a variety of restaurants, cafes and pubs to refuel and rejuvenate. Pinched on the River, a 10-minute walk toward the lake from where the boat tour ends, is a reliable spot to enjoy a meal al fresco. Suitable for those wanting a quieter environment, it’s a little removed from the other bars and taverns that cater to day drinkers while still offering exciting views of the city. The Mediterranean-inspired menu includes salads, wraps, bowls and sandwiches for every size appetite.

If you’re just in the mood for a refreshing snack, look no further than Sweet Home Gelato. Nestled on a quiet strip just west of La Salle Street, Sweet Home Gelato is the ideal spot for a cool pick-me-up. The family-owned store offers artisan gelato, milkshakes and coffee as well as baked goods, such as brownies and macaroons.

Walk half a mile west on the scenic Riverwalk, retracing some of the route you just took on the boat. You’ll pass bars with live music, tourists taking in the city, and locals soaking up the sun. As you approach the fountain, kick off your shoes and let the cool water soothe your feet.

The scent of sweet and buttery waffle cones will start to waft over, turning your attention to the compact storefront set back 15 feet from the fountain. With a smoother and denser texture, gelato is ice cream’s more sophisticated Italian cousin. Sweet Home offers gelatos in flavors ranging from classic strawberry to the more nuanced Nutella, as well as half a dozen choices of sorbet.

Choose from a decant waffle cone or a classic cup, with rainbow or chocolate sprinkles to top it off. If you are so inclined, get a boozy sundae, such as peach sorbet topped with prosecco. Sit at one of the many patio tables to enjoy your treats and watch the traffic on the Chicago River float by you.