Chicago: The Little Big City Next Door!

Just a train or bus ride away, Chicago is the perfect getaway for Ann Arbor locals looking for a change of scenery. Whether you’re craving world-class food, stunning architecture, or vibrant city energy, the Windy City delivers—without the hassle of a long trip!

Getting There: Easy & Affordable Travel

One of the best parts about visiting Chicago from Ann Arbor is how simple and affordable the journey can be. You have two main options:

• Amtrak: Take a direct train from Ann Arbor to Chicago’s Union Station. The ride is about four hours, giving you time to relax, read, or enjoy the passing scenery.

• Bus: Several companies offer direct routes from Ann Arbor to Chicago, often at lower prices than the train.

  
  

Whichever you choose, you’ll arrive right in the heart of the city, ready to explore.

Chicago’s Unmatched Vibe

Chicago isn’t just a city—it’s an experience! There’s a soul to it that you feel the moment you step onto the streets. As you walk, you’ll hear street performers filling the air with live music—jazz musicians on one corner, R&B singers on another. The city’s energy is diverse, lively, and rich in culture.

Every time I visit, it feels like stepping into the movie Love Jones—that effortlessly cool, artistic, and soulful atmosphere. One building that always gives me jazz club vibes is the Tip Top Tap. Something about it just feels like classic Chicago—like a place where history and music live in the walls.

What to Do: Chicago’s Most Beautiful Spots

Chicago is packed with stunning sights, from historic architecture to breathtaking waterfront views.

• The Riverwalk – Walking along the Chicago River feels like stepping into another world. You can even kayak on the river, taking in the skyline from a whole new perspective.

• Navy Pier & the Ferris Wheel – This iconic spot offers the best views of the city and a perfect mix of fun attractions and scenic beauty.

• Lake Michigan & the Beach – When you look across Lake Michigan, it’s like staring at the ocean—endless blue stretching into the horizon. The beach is a hidden gem in the city, a place to unwind and enjoy the water.

  
  

Where to Eat & Drink

Chicago is a foodie’s paradise, and every trip should include at least one stop for deep-dish pizza. Some of my favorite places to eat and grab a drink:

Trio French Toast Flight & Caramel Apple Butter Latte @HoneyBearCafe

• Giordano’s – Famous for its delicious stuffed deep-dish pizza.

• Lou Malnati’s – Another deep-dish icon with a buttery crust.

• Portillo’s – The go-to spot for an authentic Chicago-style hot dog.

• Honeybear Cafe – Cozy brunch vibes with huge portions and a welcoming atmosphere.

• Starbucks Reserve Roastery – The biggest Starbucks in the world, offering unique drinks and an incredible five-story coffee experience.

  
  

Why You Should Visit

Chicago offers big-city excitement with a soul you won’t find anywhere else. Whether you’re exploring its historic streets, vibing with live music, or taking in the beauty of the river and lake, this city leaves an impression.

And if you’re self-employed, keep in mind that travel, lodging, and meals can be tax-deductible—so a trip to Chicago can be fun and financially smart.

For more travel tips and local adventures, stay tuned to The Ann Arbor Hub!