Love Chicago and She Will Love You Back

“Blog Post Type: Expert Opinion Piece”

Chicago is big. It’s a metropolis. It’s a global city. Concrete and steel mountains stand tall over everything. Cars, buses, trucks, and limos play a waiting game at street corners occupied by people–suits and briefcases going to work, travelers strolling to their next attraction, and cabs being hailed by friends meeting other friends at restaurants.

Chicago Trump

Photo by Sue Cummings $ Bruce Howard via

Chicago is big. No doubt about it. It may look intimidating to outsiders, but once you start exploring, you’ll find any fear and intimidation felt dissolving. If you’re a bit anxious upon arrival, three words will help you get a feel for the city without having to walk its streets. Lake Shore Drive (LSD).

Go to the Edgewater neighborhood, get in a car, and drive the entire length of LSD to Jackson Park and back. Your journey will take you along Lincoln Park Zoo; you can glance at the city’s streets while passing the John Hancock building and see the ferris wheel on Navy Pier. View the crowds as they walk to ‘The Lake’ while you wait for the stoplight to turn green. You’ll whiz by Grant Park, Field Museum of Natural History, The Adler Planetarium, The Shedd Aquarium, Soldier Field, and finally to Jackson Park. Once accustomed to the flow of the city and its local people, there is plenty to do throughout your stay.

Chicago LSD

Photo by Sarah Pfennig via

Another way to adjust to Chicago’s pace is to take an architecture boat tour on the Chicago River. You’ll learn about the unique and distinct designs of the city’s most influential buildings from an onboard guide who is also an architect. The tour will take you through the three major branches of the Chicago River. Along the way, you’ll pass more than 40 buildings including the Wrigley Building, Willis Tower, the John Hancock Center, and the old Post Office Building that lies over Congress Parkway. Don’t be afraid to strike up a conversation while you’re on the river–you never know who you’ll meet.

Lake Shore Drive conquered. The boat tour got you closer to the concrete mountains–now it’s time to hit the streets. Nothing brings people together more than food, and Chicago’s food scene is world-renowned. A Chicago style hot dog is the perfect way to begin. This all-beef Frankfurter topped with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and celery salt on a poppy-seed bun will give you the energy to walk around. Don’t ask for ketchup. You’ll get funny looks.

Chicago Dog

Photo by throwngsofas via

After a day spent falling in love with Chicago, salute her by diving into a deep-dish pizza. Eat slice after slice until you cannot fill your stomach anymore. Then, eat one more. Catch a cab back to the La Quinta Inn & Suites Chicago Downtown where you’ll fall into a cheese coma. Don’t worry about planning your next day until you wake up. Savor the joy of your first day in Chicago. You’ll wake up wanting more.

Feature Photo by Nica F! via

About the Writer

Tony is a freelance travel writer and photographer, roller coaster enthusiast and self-proclaimed Sudoku master. He’s based in the Midwest U.S. and blogs at The Walking Traveler. He is working with Hipmunk on their #HipmunkCityLove Project.

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