Blowing into the Windy City: Chicago, Illinois
Chicago, Illinois—one of the greatest cities in the USA. Growing up in a small town nearby and later calling Chicago home for a couple of years, I’ll admit I may be a little biased. But trust me, this city has so much to offer anyone who visits. Let me walk you through what you can expect when you explore the Windy City.
Chicago Standouts
Chicago is famous for quite a few things: The Bean, hot dogs, Lake Michigan, deep-dish pizza, and of course, that jaw-dropping skyline. But my personal must-sees and must-dos are:
Walking down the Lakefront Trail
Catching a sports game (Cubs, Bulls, Bears, Sox, or Blackhawks)
Strolling along the Riverwalk
Visiting Millennium Park and The Bean
Taking a Chicago River architecture cruise
Shopping along the Magnificent Mile
The start of the Riverwalk
Bars and Food
Hot dogs, pizza, Italian beef... oh my! Chicago’s food scene is some of the best in the U.S. While the classics are a must, the city is also bursting with diverse and innovative dining options. Here are my go-to spots every time I visit:
Chicago Pizza and Oven Grinder – My favorite version of deep dish. While spots like Giordano’s get a lot of hype, this intimate Italian gem feels more authentic.
Pro tip: Make reservations ahead of time, and bring cash!Chicago’s Dog House – For a true Chicago dog, a burger, or some hearty chili fries.
JoJo’s Shake Bar – Over-the-top milkshakes, great bites, and always fun themed décor.
Paradise Park / Happy Camper – Vibrant, playful vibes with cocktails that impress and food that hits the spot. Perfect for a lively group dinner that turns into a night out.
Chicago’s Dog House
This quaint Chicago gem has mouth watering hot dogs, burgers, and fries.
Chicago’s nightlife has a little of everything—laid-back dive bars, lively sports pubs, rooftop cocktail lounges, and exclusive nightclubs. Whatever your style, you’ll find your spot. (I’ve linked my full bar recommendations in my Google Maps list below!)
Enjoy a drink with beautiful views at Offshore Rooftop
Tours and Attractions
Chicago has a fascinating history—originally Indigenous land, it grew into a trading hub, reshaped its waterways, and became an architectural icon. Even when I lived there, I loved taking tours and revisiting museums because there’s always something new to discover.
Top tours and attractions I recommend:
Chicago River Architecture Tours – (Wendella, Fireboat, etc.) – There are tons of options, and honestly, you can’t go wrong with any of them.
Shedd Aquarium – A family-friendly favorite filled with incredible marine life.
Lincoln Park Zoo – One of the country’s oldest zoos, and it’s free! Bonus: Visit in winter for the magical holiday light displays.
Laugh Factory & Second City – Chicago’s comedy scene is legendary. Prepare for a night of nonstop laughs.
Navy Pier – Great for walking, people-watching, grabbing a bite, and even hopping on a ride.
Field Museum – One of the world’s top museums—home to Sue, the most complete T-Rex skeleton ever discovered.
Willis Tower Skydeck – Head up to the 103rd floor for epic views, and if you’re brave, step onto the glass platform hovering above the city.
Transportation
Full honesty: I didn’t use public transportation in Chicago much. Not because it isn’t an option, but because I mostly drove, walked, or Ubered. A couple of tips:
Parking is pricey—expect to pay almost everywhere.
Walking or Ubering is the easiest and most stress-free way to get around, especially downtown.
Weather
Chicago isn’t called the Windy City for nothing—but it’s also a place where you truly get to enjoy all four seasons.
Summer – Hot and lively, perfect for the Riverwalk, outdoor dining, and festivals.
Winter – Cold, snowy, and magical with ice skating at Millennium Park, frozen lakeshore views, and dazzling holiday lights.
Spring & Fall – Crisp, colorful, and filled with seasonal charm.
There’s no “wrong” time to visit—it just depends on what vibe you’re after. Personally, I love summer for the energy and activity, but winter has its own unique magic.
Chicago Ratings by Wander Spree
Conclusion
Chicago always has something going on, no matter the season. Every time I return, it’s a mix of revisiting old favorites and discovering new gems. Whether you’re here for the food, the sports, the history, or the skyline views, you’re guaranteed an unforgettable trip.
I hope you get the chance to blow into the Windy City soon—it’s one of my favorites in the world.
