Most first-time visitors to Chicago are amazed by just how much there is to do. The scale of the city surprises those flying in for a weekend getaway, road trippers stopping through the Midwest, and business travelers alike — often leaving them wishing for more time. From world-class museums and distinctive dining to lakefront parks, the Chicago Riverwalk, and buzzing nightlife, the Windy City offers endless possibilities.

There’s so much to do, it would be impossible to see it all in one visit. But with a well-planned itinerary, you can experience the city’s highlights in just 72 hours. Here’s how to make the most of three unforgettable days in Chicago, with everything easily accessible from your home base at Fairmont Chicago, Millennium Park.

Day 1: Museums, Family Fun, and Blues Music

Start your adventure at the Art Institute of Chicago, home to a collection spanning centuries. Don’t miss highlights including Hopper’s Nighthawks, van Gogh’s The Bedroom, Seurat’s A Sunday on La Grande Jatte, and Wood’s American Gothic. Impressionist favorites by Monet, Degas, and Caillebotte also await, along with Chagall’s famous America Windows.

Refuel with a slice of classic Chicago deep-dish pizza at Lou Malnati’s — knife and fork required.

Traveling with kids? Chicago is home to an incredible array of family-friendly attractions. Spend the afternoon at the Shedd Aquarium, where penguins, beluga whales, and jellyfish captivate visitors. Or head to Lincoln Park Zoo (free admission) and the Peggy Notebaert Nature Museum, known for its butterfly haven.

As night falls, dive into Chicago’s legendary nightlife and music scene. Kingston Mines keeps the blues alive with alternating sets across two stages, while Buddy Guy’s Legends hosts top acts and occasional appearances by the blues icon himself.

Day 2: Millennium Park and The Magnificent Mile®

Begin your day at Millennium Park, the city’s urban centerpiece. Snap photos at the reflective Cloud Gate sculpture (aka “The Bean”), stroll through Lurie Garden, and admire Frank Gehry’s Jay Pritzker Pavilion. In summer, cool off at the interactive Crown Fountain; in winter, skate at the McCormick Tribune Ice Rink.

Cross the serpentine BP Bridge to Maggie Daley Park, where kids will love the whimsical Play Garden and, in colder months, the winding ice skating ribbon.

No trip is complete without a classic Chicago-style hot dog — piled high with mustard, relish, onions, tomato, pickle, and celery salt on a poppy seed bun (just don’t ask for ketchup!).

Next, make your way to the Chicago Riverwalk, a vibrant pedestrian waterfront lined with cafés, public art, and outdoor seating. It’s also the launching point for one of the city’s most famous experiences: an architectural boat tour. Glide along the Chicago River while expert guides share the stories behind the city’s skyline and iconic skyscrapers — a must-do for first-time visitors.

From there, head to The Magnificent Mile®, Chicago’s premier shopping district. Along the way, admire landmarks like the Wrigley Building and the historic Tribune Tower.

For dinner, savor bold Pan-Latin flavors at Toro by Richard Sandoval, conveniently located inside Fairmont Chicago, Millennium Park. End your evening with a Broadway show at theaters such as the Cadillac Palace Theatre, Chicago Theatre, or Broadway Playhouse, or catch an indie film at the Gene Siskel Film Center.

Day 3: Navy Pier and Skyline Views

Spend your final day by Lake Michigan, where 26 miles of shoreline and more than 20 beaches make Chicago feel like an oceanside city. Begin at Navy Pier, one of Chicago’s most visited attractions. Ride the 200-foot Centennial Wheel, browse shops, and enjoy live entertainment at the Chicago Shakespeare Theater. Families can explore the Chicago Children’s Museum or the immersive Amazing Chicago’s Funhouse Maze.

Snack on Garrett Popcorn’s famous caramel-and-cheese mix before heading uptown for sweeping views at 360 Chicago, the observation deck on the 94th floor of 875 North Michigan Avenue (formerly the John Hancock Building). Thrill-seekers can test their nerves on TILT, which leans you out over Michigan Avenue.

As the sun sets, wrap up your Chicago getaway with an evening of entertainment:

• Winter’s Jazz Club, an intimate, modern venue for smooth sounds
• The Green Mill, a historic speakeasy once frequented by Al Capone
• The Second City, where legendary comedians from Tina Fey to Steve Carell got their start

Where to Stay in Chicago

With so much to explore, staying central makes all the difference. Fairmont Chicago, Millennium Park places you steps from top attractions, dining, and shopping — the perfect base for your Chicago getaway.

FAQs About Visiting Chicago

How many days do you need in Chicago?
Three days is enough to see highlights like Millennium Park, Navy Pier, the Magnificent Mile, and world-class museums.

What food is Chicago known for?
Chicago’s signature eats include deep-dish pizza, Chicago-style hot dogs, and Garrett Popcorn. Plus, a meal at Toro Chicago is a must!

What’s the best time of year to visit?
Spring and fall offer pleasant weather and vibrant festivals, while summer is perfect for lakefront fun. Winter brings ice skating, holiday lights, and cozy indoor attractions.

Ready to start planning your Chicago getaway? Book your stay at Fairmont Chicago, Millennium Park today!