How to Make the Most of a 3–Day Getaway in Chicago

Experience Chicago's iconic tourist spots on day one of your three-day vacation. Start your morning at Willis Tower, offering stunning aerial views of the city. Grab delicious donuts and coffee at Stan’s Donuts and Coffee before ascending the tower. Consider purchasing a Chicago City Pass for access to top attractions like the Art Institute of Chicago and Shedd Aquarium, providing great value for first-time visitors.

Afterward, explore Millennium Park and marvel at Cloud Gate, a famous Chicago landmark. Be cautious of pickpockets in this crowded area. If you're interested in museums, use your City Pass to visit the Art Institute, Museum of Science & Industry or Field Museum, each offering unique exhibits and experiences. Walk along the Magnificent Mile, Chicago's premier commercial district, and enjoy the Chicago River Walk for scenic views and dining options.

Day two of your Chicago adventure takes you to vibrant Wrigleyville, starting with brunch in Boystown, known for its trendy coffee shops and restaurants, as well as its large LGBT community.

After brunch, head to Wrigleyville, the neighborhood surrounding Wrigley Field. If the Cubs are playing, this area buzzes with excitement and energy. Enjoy lively sports bars and pubs like Old Crow, a two-story venue with great atmosphere and throwback music. Another must-visit spot is Sluggers, known for its indoor batting cages and divey vibe.

For a quick bite, grab a slice or two at Dimo’s, known for delicious pizza varieties. If you're a first-time visitor, consider centering your day around attending a Cubs game at historic Wrigley Field. It's an iconic experience with passionate fans and classic ballpark food like hot dogs and beer. Whether you're a baseball fan or not, the lively atmosphere at Wrigley Field is worth experiencing during your Chicago visit.

Insider Tip: Arrive early for a Cubs game to soak in the pre-game excitement at nearby bars like Old Crow and Sluggers. This area is bustling with activity during game days, offering a quintessential Chicago sports experience.

Day three of your Chicago itinerary features an exhilarating boat cruise, a perfect blend of music, drinks and breathtaking skyline views. Starting with a homemade breakfast, you'll head to the pier for a midday departure. The cruise offers three levels, including a lively top deck with a DJ and stunning open-air views of Chicago's skyline.

This unforgettable experience unfolds with upbeat music, great weather and a vibrant atmosphere. The four-hour cruise flies by, leaving everyone enchanted by the cityscape. Afterward, unwind at Federales, a vibrant Mexican tequila bar, for delicious food and drinks.

For travelers seeking more activities, consider the architecture river tour, a favorite among architecture enthusiasts, showcasing Chicago's iconic skyscrapers along the river. Learn about the city's unique post-fire building design and its impact on sunlight accessibility.

If time allows, explore Navy Pier, home to attractions like a Ferris wheel and a food hall. While not a must-visit, it offers a taste of Chicago's waterfront charm. Don't miss the chance to try deep-dish pizza at Giordano's.

For a more active day, rent a Divvy bike and cruise down the Chicago Lakefront Trail, a scenic 18.5-mile path along Lake Michigan. Opt for electric-assist bikes for an easier ride or regular bikes for a challenge.

Insider Tip: Book boat cruises in advance, especially during peak tourist seasons, to secure preferred time slots. For the architecture tour, consider early morning or evening slots for fewer crowds and better photo opportunities of the skyline.