How to Spend 48 Hours in Chicago?

Whether it’s a quick weekend getaway or an extended stay, Chicago offers visitors plenty of ways to take in its renowned landmarks, world-famous cuisine and its distinctive neighborhoods. It’s home to a whole host of great museums, theaters, galleries, parks and more – so if you’re looking for a lively 24 hours in the windy city, it’s possible to hit the highlights without feeling rushed. Here’s a fun itinerary that you can use to make the most of your 48 hours in Chicago.

Day 1

Early Morning Start at Navy Pier

Start your day living that famous Chicago skyline – Navy Pier is one of the city’s iconic landmarks and a great place to start your adventure. The pier is filled with attractions, from the Children’s Museum to the carousel and beyond. Plus, it’s a great spot to while away some time – particularly with a cup of coffee or Americano and a pastry from the cafés that circle the pier. Once you’ve had breakfast, head over to the glass-enclosed Grand Ballroom, where you can take in a single kayak or take part in a restaurant-looking tour.

Walk the Magnificent Mile

Out front of Navy Pier lies the Magnificent Mile – a stretch of Michigan Avenue straddling downtown to the historic Gold Coast. It’s filled with popular stores and boutiques like Macy’s and Bloomingdale’s, as well as a dazzling range of architecture from the Gothic Tribune Tower to the Art Deco Wrigley Building. You could also take a stroll up towards North Avenue for one of the city’s hippest galleries and markets. While you are there, don’t forget to look out for Chicagoans and visitors alike enjoying the lakefront views from Oak Street Beach – one of Chicago’s famed beaches.

Noon Stop at Millennium Park

As you continue your journey through the Windy City, you can take a break at Millennium Park. This iconic park is home to some of the city’s most striking landmarks, like Cloud Gate, the Crown Fountain and Jay Pritzker Pavilion – all of which are worth checking out. After taking in the views and going on an urban hike up to the Lurie Garden, you can refuel with sandwiches and snacks from Jay Pritzker Pavilion and enjoy lunch outside.

Visit Shedd Aquarium

When it comes to museums and galleries, Chicago Aquarium is definitely one of the city’s most recognizable. Home to over 32,000 aquatic animals ranging from sharks to piranhas and even beluga whales, Chicago Aquarium offers plenty of educational activities and hands-on experiences, so it’s the perfect space to explore the world undersea. Before you leave, don’t miss the Amazon Rising exhibit and its interactive multimedia display.

Day 2

A little bit of Education at the Museum Campus

Kick off Day 2 with a visit to the Museum Campus, which hosts three of Chicago’s must-see attractions: The Field Museum, Adler Planetarium and Shedd aquarium. Here you’ll find a wealth of exhibits, galleries and interactive experiences – perfect for family days out. Families may also want to check out the dinosaurs in Field Museum or explore the stars in Adler Planetarium – whatever you choose to explore, each institution has plenty of fun ideas for engaging children.

Navigate Castles on Lake Michigan

Next on your itinerary should be taking a boat tour on Lake Michigan. From here you can take in amazing views of Chicago’s skyline as well as navigating past mansion-style homes or castles dotting the lakefront. Not only is this a great way to get a different perspective on Chicago but it can be romantic too! So make sure you check out a boat tour when you have time.

Hit Up Historic Lincoln Park

Often overlooked but just as stunning is Lincoln Park – a larger public park than Millennium Park. Visitors are spoiled here with beautiful views of beaches, gardens, monuments, lagoons and more. Plus, you can find a peaceful tree canopy to explore when its hot outdoors. And don’t forget to check out where locals picnic and grill through the summer months.

The End of It All at Willis Tower & Cloud Gate

End your two days in Chicago with a trip up Willis Tower – home to one of the most iconic views in Chicago – as well as some dangerous glass bridegways over 100 stories up! Entry includes an audio tour around this entertaining landmark – where even playing hopscotch up there gives you an amazing view. Then make sure you end your trip exploring Cloud Gate – locally called “The Bean” – located at the end of Millennium Park near Grant Park. Sculpted from stainless steel sheets at its base, Cloud Gate is truly an artistic masterpiece.

No matter what your preference for 48 hours in Chicago might be, there is an endless range of entertainment that can be enjoyed thanks to the Windy City! From taking pictures with breathtaking skylines of Navy Pier and Willis Tower to walking around magnificent parks like Lincoln Park and Millennium Park – Chicago offers adventures that are unique and exciting.

Explore Time Out’s comprehensive guide for other fun activities to do during 48 hours in Chicago.