Welcome to Chicago, where the pizza is deep, the architecture is bold, and the wind is always in your face (literally). Whether you’re here for the skyline, the museums, or just to pretend you’re in a scene from Ferris Bueller’s Day Off, Chicago has it all—minus the hassle of figuring out if that cloud is a rainstorm or just lake effect weather.
Why Visit Chicago:
Chicago is a bustling metropolis with Midwestern charm, offering an unbeatable combination of arts, culture, food, and sports. From the iconic Willis Tower (yes, it’ll always be Sears to us) to the mesmerizing works at The Art Institute, the city caters to all interests. It’s also home to some of the finest food you’ll ever eat—whether it’s a Michelin-star meal or a Chicago dog piled high with toppings (just don’t ask for ketchup).
How Long You Should Spend in Chicago:
Three to five days is the sweet spot for a visit to Chicago. You’ll have enough time to hit the major attractions, sample the local cuisine (which might take longer than you think), and maybe even squeeze in a Cubs or Sox game depending on your loyalties.
Top 10 Can’t-Miss Things to Do in Chicago:
- Willis Tower Skydeck – Step onto the Ledge at 1,353 feet for a view (and a thrill) you’ll never forget. If you’re afraid of heights, just look at the floor.
- Millennium Park & The Bean (Cloud Gate) – Yes, it’s just a giant, reflective bean, but try not to take 100 pictures of yourself in its shiny surface. We dare you.
- The Art Institute of Chicago – Home to classics like American Gothic and A Sunday on La Grande Jatte, plus a lot more impressive artwork that’ll make you look smart.
- Navy Pier – Rides, food, and gorgeous views of Lake Michigan—what’s not to love? Plus, you can catch a boat tour for an even better look at the city skyline.
- Museum of Science and Industry – If you like science, history, and massive train exhibits (who doesn’t?), you’ll have a blast here.
- Chicago River Architecture Tour – Learn the stories behind Chicago’s stunning skyline on this popular boat tour. Bonus: No walking involved!
- Wrigley Field – Even if you’re not a baseball fan, Wrigley Field is worth a visit for its history, charm, and ivy-covered walls. Plus, they serve beer.
- Lincoln Park Zoo – One of the last free zoos in the U.S., this is a great spot to take the kids—or just relive your childhood without spending a dime.
- 360 Chicago Observation Deck – Located at the John Hancock Center, this observation deck offers views rivaling Willis Tower. Feeling brave? Try the Tilt ride.
- Chicago’s Theater District – Catch a Broadway show or local production in one of the historic theaters. It’s like NYC but with better pizza.
Top 5 Popular Hotels in Chicago:
- The Langham, Chicago: Elegance meets comfort at this riverside hotel, offering incredible views, a spa, and afternoon tea that’ll make you feel fancy.
- The Peninsula Chicago: Luxury at its finest, with rooms so plush you might never want to leave. But you should, because it’s Chicago after all.
- The Gwen, A Luxury Collection Hotel: Located on Michigan Avenue, this stylish hotel offers an incredible rooftop bar and is perfect for shopaholics.
- LondonHouse Chicago: Situated right by the Chicago River, this hotel boasts a rooftop bar with some of the best views in the city.
- Virgin Hotels Chicago: Trendy, fun, and pet-friendly, Virgin Hotels offers modern rooms with a youthful vibe. Don’t forget to check out their rooftop bar, Cerise.
Top 10 Restaurants in Chicago:
- Alinea: Fine dining at its most creative. With three Michelin stars, dining here is more like an experience than a meal. Your taste buds will thank you (your wallet, maybe not so much).
- Girl & The Goat: Chef Stephanie Izard’s inventive menu mixes global flavors in a way that’ll make you want to order everything. Pro tip: do it.
- Lou Malnati’s Pizzeria: Chicago-style deep-dish pizza. Enough said. Just bring your appetite and maybe some stretchy pants.
- Giordano’s: Another deep-dish legend. The pizza here is so thick it feels like a meal and a workout all in one.
- Au Cheval: Famous for its burger, this spot has a cult following for a reason. One bite and you’ll understand why it’s often called the best burger in America.
- The Purple Pig: Small plates and a great wine list make this a go-to spot for foodies. Don’t miss the bone marrow.
- RPM Steak: If you’re craving a steakhouse experience, RPM delivers with style and impeccable service.
- Smoque BBQ: Chicago may not be known for barbecue, but Smoque will change your mind with its smoked meats and addictive sauces.
- Joe’s Seafood, Prime Steak & Stone Crab: A Chicago classic, famous for (you guessed it) stone crabs and steaks. Reservations highly recommended.
- The Publican: Farm-to-table dining with a focus on meats, seafood, and vegetables that are as fresh as they come.
Best Month to Visit Chicago:
Visit Chicago between May and September to enjoy outdoor festivals, baseball games, and pleasant weather (most of the time). Winters here are legendary—and not in a good way—so unless you’re into sub-zero temps, visit when the city is warm and welcoming.
Chicago’s Best Kept Secret:
Head to Montrose Beach for a peaceful escape from the city’s hustle and bustle. It’s also one of the few beaches where you can bring your dog, so Fido can frolic in the sand while you relax and soak up views of the skyline.
Chicago is a city that never disappoints. From towering skyscrapers and world-class museums to iconic deep-dish pizza and a vibrant theater scene, it’s impossible to leave the Windy City without falling in love. Whether you’re gazing up at the Bean or down from the Skydeck, Chicago offers endless adventures that will blow you away. Just don’t forget your jacket—it’s called the Windy City for a reason.