For my final stop, the “Windy City” was pleasantly warm. The heart of downtown was stirring with a nice spring breeze off of Lake Michigan that even a fifteen-hour, showerless train ride could not ruin. It has been an incredible experience but in all honesty I have become a bit jaded by city attractions, “must-sees” and museums of any kind. However, meeting up with my friends Eliza, Jim, and their friend Patrick was a perfect ending to a long journey. We caught up over an early dinner at a nearby pub on the North Side before catching the bus downtown to walk through the city. The unseasonably nice weather coaxed jackets off even the most skeptical Chicagoans, my tour guides included. They brought me through an interesting model of the city before we walked into the famed millennium park to see what was surely an acid induced creation, but nonetheless incredible sculpture known as “The Bean”. Continuing up Michigan Ave. Jim and Patrick, who are working in engineering and landscape architecture respectively, gave me a brief history of every interesting building we passed. It was a unique way to walk a city and was nice to get it for free. We then took advantage of a secret only known by the most savvy deal-hunters –the lounge at the top of the Hancock Tower. Instead of paying the $20 fee to get off at the Observatory, we rode the elevator one floor up and only paid $8.25 for a drink in the lounge, which gives equally expansive views of the sprawling city and is not overrun with tourists. It was especially beautiful at night, the lights and streets traced the neighborhoods like veins through an arm.
After a drink at the Hancock Lounge we jumped back on the bus uptown to enjoy another of Chicago’s secrets. Known for their famous Char-Dog and Chocolate Shake, the Weiner’s circle was an exceptional way to end the night. The Char dog includes mustard, tomatoes, a full pickle, and some type of neon green relish that, separate may sound unappetizing, but together form the perfect hot-dog. On top of that, the chocolate shake was unlike any other I have tasted. Truly out-of-this-world –good. The blend of light and dark chocolate, and ice cream that seemingly bounces with flavor made for an experience I will never forget. If you do nothing else in Chicago, you need to go to The Weiner’s Circle and order a Chocolate Shake. They tend to be on the expensive side, but believe me, its worth every sip.
Chicago was an unexpected highlight of my trip and although I was a beaten down traveler I genuinely enjoyed my time there. I was glad to pull out of Union Station headed East, and even the twenty-four hour train ride ahead of me did not dilute my excitement for getting home.


Congratulations Sean! Job well done. I have enjoyed learning of your travels this past month. You covered a great deal of territory and had a wonderful taste of the US. Weather, people, places and things! Thank you for sharing your trip with so many people. Welcome back to the East Coast;
home is always a great place to return to!!
Glad you are back in this neck of the woods! Thanks so much for the great descriptions of your stopping points………very entertaining!
A project well done………
Am I wrong to think there may be more to tell about Venice Beach?
Sounds like you had an awesome trip. The descriptions of each city were wonderful. They made me wish I was there.
Hi, Sean! What a fun and exciting whirlwind trip to Chicago! As a former resident, I agree, your friends did an outstanding job showing you the city. I am the custom media editor at Midwest Living magazine and we’re working with Enjoy Illinois on a Facebook contest called, “Magnificent Getaways Giveaway Contest,” which invites people to share recent magnificent Illinois experiences for a chance to win one of three one-of-a-kind, once-in-a-lifetime experiences in Chicago and across Illinois. Here’s your chance to see even more Chicago attractions! The Grand Prize alone includes dining (for four) on the Ledge at Skydeck Chicago, a stay at the Trump Tower and admission and VIP behind-the-scenes tours at the Art Institute of Chicago, Shedd Aquarium and the Museum of Science and Industry! If this is something you’re interested in you can enter one of two ways: http://www.facebook.com/enjoyillinois or on the contest website, http://magnificentgiveaway.com. Please feel free to contact me with any questions at kristin.bienert@meredith.com. Thanks! Kristin Bienert, Custom Media Editor for Midwest Living magazine, Meredith Corporation