If you’ve ever dreamed of a city that blends lakefront beauty with architectural swagger, world-class museums, and food so bold it becomes an identity—welcome to Chicago. Known as the “Second City,” Chicago is anything but second-rate when it comes to offering unforgettable travel experiences. Whether you’re planning a weekend getaway or plotting your ultimate USA city break, here’s your essential guide to what to do in Chicago—from iconic sights to secret delights.
1. Start With Art: The Art Institute of Chicago
Step into a world of masterpieces spanning over 5,000 years at the Art Institute of Chicago. With gems like American Gothic by Grant Wood and The Bedroom by Van Gogh, this centrally located museum is a perfect morning stop before the crowds arrive. Bonus tip? The leafy Millennium Park is right next door—perfect for a breather.
2. Reach the Sky: Willis Tower & 360 Chicago
There are two iconic towers that offer sweeping city views—Willis Tower (formerly Sears Tower) and 360 Chicago, located atop the former John Hancock Center.
- Willis Tower offers a classic 360-degree observation deck, once the tallest building in the world.
- 360 Chicago features the Tilt attraction—glass windows that tilt you over Michigan Avenue from the 94th floor. Brave the glass and soak in views of the lake and skyline that will leave your Instagram glowing.
Want to save on both? Look into the Chicago CityPASS, which grants access to multiple top attractions.
3. Millennium Park: Meet The Bean & Catch a Concert
In the heart of the Loop lies Millennium Park, home to Cloud Gate (affectionately called The Bean) and the Jay Pritzker Pavilion, an outdoor venue hosting live jazz festivals and events throughout the year. It’s one of Chicago’s most photographed spots and always buzzing with energy.
4. Explore the Water: Lake Michigan & The Riverwalk
Don’t miss Chicago from the water. Choose your style:
- Sail, kayak, or hop on a water taxi along the riverfront.
- Head to Navy Pier to rent jet skis or book a scenic lake cruise.
- Stroll or bike the Lakefront Trail, an 18-mile stretch lined with beaches, skyline views, and green spaces.
5. Visit the Museums That Make Chicago a Cultural Giant
Chicago has some of the best museums in the U.S., and many are perfect for families or curious minds:
- Museum of Science and Industry: Massive toy train tracks, indoor tornados, and real space capsules. Admission: US$21.95 adults, US$12.95 kids.
- The Field Museum: Dinosaur skeletons, rare fossils, and 40 million artifacts celebrating natural history. Part of the CityPASS or US$29 general admission.
- Shedd Aquarium & Adler Planetarium: Nearby and perfect if you’re building a museum-heavy day itinerary.
6. Navy Pier & The Centennial Wheel
Stretching 3,300 feet into Lake Michigan, Navy Pier is a festive spot filled with eateries, a Shakespeare theater, souvenir shops, and its showstopper—the Centennial Wheel. For just US$15, get climate-controlled gondola views of the Chicago skyline and lakefront.
7. Shop the Magnificent Mile & Stroll the Riverwalk
The Magnificent Mile is Chicago’s upscale shopping mecca, packed with flagship stores, historic buildings like the Tribune Tower, and high-rise malls like Water Tower Place. Nearby, the Chicago Riverwalk offers al fresco dining, public art, and a relaxing walk along the water—especially dazzling at golden hour.
8. Take a Break on the Beach
Yes, Chicago has beaches—with vibrant blue water that will surprise you. Locals love jogging, biking, or simply sunbathing along Lake Michigan. Rent a Divvy bike and cruise from Grant Park to Oak Street Beach. Stop for a picnic or a lakeside espresso.
9. Taste Chicago’s Culinary Icons
No trip is complete without trying these local bites:
- Deep Dish Pizza: Head to Giordano’s or Lou Malnati’s for the classic cheesy behemoth.
- Chicago Dog: A beef hot dog with everything—mustard, onions, relish, tomato, pickles, and celery salt on a poppy seed bun.
- Italian Beef Sandwich: Slow-roasted beef piled high on crusty bread, dipped in savory jus.
- Chicago Steakhouse: Splurge on a ribeye in a city that takes its meat seriously.
- Oysters & Seafood: Yes, you can have fresh oysters by the lake.
- Nutella Café: For a sweet ending, grab a pastry at this one-of-a-kind dessert haven.
10. End With a Show
Chicago’s theater scene is electric. Catch a performance at the historic Chicago Theatre, or check the listings for improv, Broadway hits, and local productions throughout the city.
Your Perfect 3-Day Chicago Itinerary:
Day 1: Millennium Park → Art Institute → Deep Dish Lunch → 360 Chicago Sunset
Day 2: Museum of Science → Field Museum → Lakefront Trail → Chicago Dog Picnic
Day 3: Navy Pier → Centennial Wheel → Magnificent Mile → Chicago Riverwalk Dinner & Night Show
Whether it’s your first visit or your fifth, Chicago always has something new to offer. It’s a city where the arts, skyline, and street food come together in perfect harmony. And if you follow this guide, you’ll get the perfect taste—just like a slice of deep dish, served hot and unforgettable.
Or why not see some cool tips and ideas from others who have traveled in the US over here.
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