How to Spend 72 Hours in Chicago: Top Attractions and Dining Spots

Chicago is a bustling city full of iconic landmarks, stunning architecture, and mouthwatering food. After visiting for a short weekend, I have fallen in love with the windy city! Whether you’re visiting for the first time or making a return trip, 72 hours is enough time to experience the heart of the city. In this guide, we’ll explore the best of Chicago’s downtown, from iconic tourist spots to can’t-miss foodie bites.

Day 1: Explore the City’s Icons and Enjoy Classic Eats

Start with a City Transit Pass

Kick off your Chicago adventure by purchasing a weekend city transit pass for $15, which grants you unlimited train and bus rides throughout the city. This makes exploring Chicago easy and affordable.

Morning: Wake and Bakery

For breakfast, head to Wake n Bakery, a cafe that’s as unique as it is delicious. Known for its infused drinks and edibles, this spot offers a laid-back vibe to start your day on a high note—literally! Grab a coffee or one of their signature drinks before heading out to see the sights.

Midday: Millenium Park

Next, take a stroll over to Millennium Park, home to one of Chicago's most famous landmarks: The Bean (officially known as Cloud Gate). After snapping a few photos, explore the park's outdoor festivals or cool off by the Crown Fountain. There’s plenty of open space to sit back, relax, and people-watch. It’s a perfect blend of nature and urban life.

Lunch: The Harding Tavern

By now, you’ve likely worked up an appetite. Stop by The Harding Tavern, a cozy spot offering a range of delicious dishes from burgers to salads. This gastropub is known for its welcoming atmosphere and hearty portions, making it a great choice to refuel after your morning in the park.

Afternoon: Navy Pier and Skydeck

In the afternoon, take a walk along Navy Pier. With its shops, restaurants, and entertainment options, it's a popular tourist destination and perfect for a leisurely stroll. Afterward, head to the Skydeck at the Willis Tower (formerly Sears Tower) for jaw-dropping views of Chicago's skyline. Standing 1,353 feet above the city, this is a must-see experience.

Dinner: Giordano's for Deep Dish Pizza

No trip to Chicago is complete without trying the city’s famous deep dish pizza. For dinner, head to Giordano’s, one of the top spots for this cheesy, delicious indulgence. Whether you prefer classic toppings or something a little more adventurous, Giordano's is a satisfying way to wrap up your first day.

Day 2: Dive Into Art, Culture, and Chicago’s Nightlife

Morning: WNDR Museum

Begin day two with a visit to the WNDR Museum, an interactive art space that blends creativity and technology. You’ll find yourself immersed in thought-provoking exhibits that are perfect for those who love interactive and Instagram-worthy experiences.

Evening: Z Bar

In the afternoon, head to Z Bar for drinks with a view. Located on the rooftop of The Peninsula Hotel, Z Bar offers a chic, intimate atmosphere. Sip on craft cocktails while taking in panoramic views of downtown Chicago. This is an excellent spot to unwind after your morning museum visit.

Dinner and Late-Night Chill: Bijan’s Bistro

For dinner, enjoy an evening at Bijan’s Bistro. Known for its late-night hours and cozy, relaxed vibe, this restaurant is a local favorite for winding down after a busy day. The menu features a variety of American and Mediterranean-inspired dishes, perfect for any palate. Whether you’re stopping in for dinner or late-night eats, Bijan’s won’t disappoint.

Day 3: Architecture, River Views, and Last-Minute Adventures

Morning: Bag Drop at Baggage Help

Before embarking on your final day, drop off your bags at one of Baggage Help’s locations for just $5 per bag. I used their downtown location, which was incredibly convenient and hassle-free, allowing me to explore the city hands-free before my flight.

Midday: Chicago Riverwalk and Architecture Boat Tour

Next, take a leisurely walk along the Chicago Riverwalk, a pedestrian-friendly pathway that offers beautiful views of the city’s architecture and river. If you’re curious to learn more about the history and design of Chicago’s most famous buildings, hop on an Architecture Boat Tour. This informative cruise takes you along the river while guides share fascinating stories about the city’s iconic skyline.

Lunch: CocoBar

For lunch, head to CocoBar along the riverfront. The views of the Chicago River alone make this a standout spot, but the menu takes it to another level. Build your own margarita and pair it with their signature loaded nachos for a truly satisfying meal. The vibrant atmosphere is the perfect midday break as you prepare for the afternoon.

Afternoon: Navy Pier and FlyOver Chicago

Spend the afternoon revisiting Navy Pier, one of Chicago’s most popular attractions. If you missed it on day one, now’s the time to explore its shops and scenic spots at a more leisurely pace. For a fun and immersive experience, check out FlyOver Chicago, a simulated flight experience that takes you on a virtual journey over the city and its landmarks.

Three days in Chicago offers a whirlwind of activities, from exploring its famous parks and landmarks to indulging in its world-renowned cuisine. Whether you’re soaking in the city’s rich history or diving into its vibrant nightlife, this 72-hour itinerary gives you a perfect balance of culture, adventure, and relaxation. Make sure to bring your appetite and your camera—you’ll leave Chicago with full hearts, full bellies, and plenty of memories to take home.

For your convenience, you can download the attached itinerary to use on the go, and don’t forget to check out the Google Maps link for the best hotspots downtown. This will help you easily navigate the must-see attractions and top dining spots during your trip.

Enjoy your time in Chicago!