Chicago Travel Guide: What to See, Eat & Experience
If you’re planning a trip to the Windy City, you probably have a list of must‑see spots already. Let’s cut through the hype and focus on the places that really give you a taste of Chicago without wasting time or money.
Must‑see sights in Chicago
The skyline is the first thing you notice, and the best way to get up close is by walking the Lakefront Trail. This 18‑mile path runs along Lake Michigan and offers unbeatable views of the city’s iconic towers. Stop at Millennium Park to snap a selfie with the famous ‘Bean’ sculpture – it’s a photo‑op that never gets old.
For a deep dive into art and architecture, head to the Art Institute of Chicago. Its collection spans centuries, but the modern wing is where you’ll find bold pieces that speak to today’s vibe. If you love heights, the Willis Tower Skydeck still draws crowds, but try the 360 Chicago Observation Deck for a smoother line and interactive exhibits.
Culture lovers should not miss the Chicago Cultural Center. Free entry, a stunning stained‑glass dome, and rotating exhibits make it a solid stop for a quick cultural fix. And if you’re into neighborhoods, wander through Wicker Park or Logan Square for street art, indie boutiques, and coffee shops that feel like a hidden gem.
Food & drink you shouldn’t miss
Chicago is famous for its deep‑dish pizza, but there’s more on the menu. Grab a slice at Lou Malnati’s if you want the classic buttery crust, or try Pequod’s for caramelized edges that crackle each bite.
Don’t overlook the city’s hot dog culture. A true Chicago‑style dog comes with mustard, relish, onions, pickle spears, tomato slices, sport peppers, and a poppy‑seed bun – no ketchup! Head to Portillo’s for a reliable version, or hunt down a local stand for a more authentic feel.
If you’re after something lighter, the West Loop is packed with upscale eateries that serve farm‑to‑table plates. The Girl & the Goat offers bold flavors that keep locals coming back, while Frontera Grill serves up fresh Mexican dishes with a Chicago twist.
For drinks, the city’s craft‑beer scene is booming. Visit Lagunitas Brewing Company or Half Acre Beer Company for a tasting flight that showcases local hops. If you prefer cocktails, the speakeasy vibe of The Violet Hour in Wicker Park is a perfect spot to unwind after a day of sightseeing.
Getting around is easy with the CTA’s ‘L’ trains and buses. Purchase a Ventra card, hop on any line, and you’ll be minutes away from each major district. Walking is also a great option for downtown – the streets are compact and packed with hidden cafés and street performers.
Finally, plan a little extra time for a lake‑front sunset. Head to Navy Pier early, avoid the crowds, and watch the sun dip behind the skyline while the lake reflects a golden glow. It’s the kind of moment that makes any trip feel unforgettable.
With this quick guide, you’ve got the essentials sorted. Pack comfortable shoes, bring a hearty appetite, and let Chicago’s energy lead the way. Happy travels!
14 Feb 2023
