If you’ve never been to Chicago, you may only equate it to Oprah, the Cubs and windy and cold winters. Dig a bit deeper and you’ll realize this influential city offers locals and visitors alike some of the nation’s best jazz clubs and improvisation troupes, world class shopping, restaurants, an amazing skyline and phenomenal architecture.
One of the best ways to learn about Chicago’s unique array of architecture, fun facts about the city and spend some time on the Chicago River and Lake Michigan is to begin your day heading to the Southwest corner of Michigan Avenue and Wacker Drive for the 90-minute morning Wendella boat tour.
Ads are how we pay our bills and keep our blog free for you to enjoy. We also use affiliate links; if you make a purchase through them, we may receive a small commission at no cost to you.
Sit back and relax as the boat heads up the Chicago River and enjoy the live narration detailing some of the city’s most interesting and famous buildings. Because many structures within the downtown area were destroyed by the 1871 Great Chicago Fire, buildings here are not known for their antiquity but instead for the diversity of their architectural styles.
The trip includes voyaging through the Chicago Lock and onto Lake Michigan. From this vantage point you can take in the true splendor of this cosmopolitan cityscape.
After the tour, head just around the corner on Michigan Avenue and enjoy lunch at the Billy Goat Tavern and Grill. There are several locations, but this underground tavern is the original and has been around since 1934. They serve up a variety of sandwiches, hot dogs and burgers, but food isn’t not the only thing they are famous for.
Legend has it that the owner of the tavern, William “Billy Goat” Sianis put a curse on the Cubs during the 1945 World Series when they wouldn’t allow him and his pet goat into game four of the Series. He declared “The Cubs ain’t gonna win no more. The Cubs will never win a World Series so long as the goat is not allowed in Wrigley Field.”
So, it’s been a mere 64 years since he uttered his words and the same amount of time since the club played in the World Series. I guess the curse has stuck and today it’s known as the “Curse of the Billy Goat,” or the “Cubs Curse.
On the lighter side the tavern was also the inspiration for the Saturday Night Live sketch “Cheezborger! Cheezborger! No fries, cheeps! No Pepsi, Coke!”
After lunch, continue on Michigan Avenue toward Lakeshore Drive in pursuit of some serious window shopping. Known as The Magnificent Mile, it’s Chicago’s version of the Champs-Elysées or Rodeo Drive. You’ll find all the high end regulars like Tiffany, Neiman Marcus, Saks Fifth Avenue, Cole Haan and much more.
For a bird’s eye view of the city, head to the Hancock Tower for a ride on the fastest elevator in North America. Once you reach the 94th floor in just 39 seconds, walk around and take in 360 degree views that include seeing four states on a clear day; Illinois, Indiana, Michigan and Wisconsin.
While not as tall as the Sears Tower, the proximity to Lake Michigan and the spectacular view makes the Hancock Tower well worth the visit.
If you want the view and are willing to forgo some of the interesting history shared at the Observatory, head to the 96th floor Signature Lounge and enjoy a beer or cocktail. You’ll get the same lakeside view of the city without the throngs of tourists or entrance fee.
Afterwards, continue down Michigan Avenue until it turns into Lakeshore Drive. Running parallel with and alongside the shoreline of Lake Michigan, East Lake Shore Drive District is a historic district that includes luxury high rise apartment buildings and the Drake Hotel.
Continue your walk heading to Oak Street to some of Chicago’s most exclusive boutique shopping and high end salons. Stores on the street include Prada, Barneys New York, Hermès, Tod’s, Yves Saint Laurent, Kate Spade, Jil Sander, Loro Piana, Furla, calypso, Judith Ripka, Frette, Marina Rinaldi, Agent Provocateur, Juicy Couture, Luca Luca, Graff Diamonds, Harry Winston, Vera Wang, Wolford Boutique, Me&Ro, A pea in the pod, ACA All Custom Attire, AG Jeans, Diesel, BCBG Max Azria, Bang & Olufsen, Paul Stuart & Phineas Cole, and Chicago’s own Ultimo. Wow, that was a mouthful!
For dinner head to Rush Street for dinner at a local’s hangout: Tavern on Rush. This is a prime spot to people watch if you can score a table outside and assuming the weather is cooperating. Start with tomato bisque soup and for your entrée try the grilled pork chop served with a Granny Smith Apple Compote or the honey mustard glazed grilled swordfish served with Fingerling Potatoes, Corn, Asparagus and Carrots.
After a day exploring the Windy City, you may just feel like a local. How could you not? You’ve learned about the city architecture and history, taken in views of the city from Lake Michigan and from the Hancock Observatory, walked the cities most famous streets and shopped like a pro.
What & Where:
Billy Goat Tavern Original (430 N. Michigan Ave at Lower Level; 312-222-1525)
John Hancock Observatory (875 N. Michigan Ave; 888-875-8439)
Tavern on Rush (1031 N Rush St; 312-664-9600)