48 Hours in Chicago: The 8 Best Things to Do

If you’ve only got 48 hours in Chicago, don’t worry… while you may not see everything this amazing city has to offer, you can certainly cover the highlights and the best things to see and do. In a city as fabulous and sprawling as the Windy City, there’s something for everyone. It’s packed with beautiful, iconic buildings, and incredible architecture. And, don’t get me started on the endless food and entertainment options. We wandered around Chicago for a weekend, found some great things to see, and of course, thanks you don’t want to do (I left those out!).

Here’s the 8 best things to do: a perfect 48-hour Chicago itinerary

wha to do with 48 hours in Chicago

Day 1 – 48 hours in Chicago

Walk through Millennium Park

Start with an early morning walk through Millennium Park. Millennium Park is said to be the pride of the city. It’s home to the iconic “Cloud Gate” sculpture, commonly known as “The Bean,” for its bean-like shape. Try to get there as early as possible before the crowds arrive to snap a picture of the Bean’s gleaming reflection. Walking around Millennium Park not only offers a glimpse into many of Chicago’s famous art installations, but the park itself is a showcase of modern architectural design. If you’re lucky, you’ll catch one of the temporary art exhibits or performances that add to the cultural experience of this beautiful park.

millennium park chicago

Explore the Art Institute of Chicago

Just a short walk from Millennium Park is the Art Institute of Chicago, a world-renowned museum holding treasures from across the globe. Spend a few hours wandering through galleries that house works by Van Gogh, Seurat, and Monet among many others. Don’t miss the Thorne Miniature Rooms or the Chagall stained glass windows. This museum is a must-visit for art lovers and history buffs alike.

Grab Lunch at the Navy Pier

Head over to Navy Pier for a lunch experience that offers much more than just food. This iconic landmark stretches over Lake Michigan and if filled with a variety of dining options, great scenic vibes and endless shopping. Since you only have 48 hours in Chicago, I highly recommend trying the classic Chicago deep-dish pizza here, and then you can walk it off with a leisurely walk around the pier. It’s easy to hop on one of the many boat tours offered if you want to get a different perspective of the impressive Chicago skyline.

visit the MCA museum with 48 hours in Chicago

Visit the Museum of Contemporary Art (MCA)

After lunch, make your way to the Northside of Chicago and visit the Museum of Contemporary Art. This museum is located by the Magnificent Mile, which is Chicago’s fancy district known for its shopping, dining, and entertainment options. The MCA is filled with an eclectic mix of contemporary pieces and interactive installations and often features thought-provoking exhibitions from artists around the world. We were definitely inspired by the ‘Nicole Eisenman: What Happened’ exhibit as she addresses through her work key political and social concerns shaping the world today.

48 hours in Chicago: the perfect 2 day itinerary

Dinner and Drinks on a Rooftop Deck

After a quick rest to recharge for the evening, you can head to one of Chicago’s renowned rooftop bars or restaurants for dinner and drinks. It’s a perfect spot to enjoy the views from the top of the beautiful architecture. Pro-tip: try to arrive a little before sunset so you can be settled into your table and watch the city lights twinkle over the infamous skyline and river. It’s a perfect way to toast to your whirlwind 48 hours in Chicago.

We visited the rooftop bar at LondonHouse in Chicago and found great views and a vibrant atmosphere that’s hard to match. It’s on the 22nd floor of the historic LondonHouse building, and it delivers those stunning panoramic views of the Chicago River, Lake Michigan, and the magnificent city skyline. It has a modern flair and plush seating, and the ambiance invites you to relax. It’s an ideal spot to unwind, socialise, and take in the breathtaking sights of downtown Chicago.

Take a Night Walk or Enjoy Some Jazz

After dinner, and assuming you have the energy, you can take a stroll along the Magnificent Mile for some late-night shopping and sightseeing. Alternatively, Chicago is filled with jazz clubs offering soulful live music to end your evening. It’s the perfect place for a nightcap and immerse yourself in the city’s rich blues culture.

explore the architecture with 48 hours in chicago

Day 2 – 48 hours in Chicago

Start your morning with a hot coffee and warm, gooey cinnamon roll; a local favorite and delicious sweet treat. Then take a leisurely stroll through the city streets and soak in the stunning architecture.

Visit the Sears Tower

Well, the Sears Tower is now called the Willis Tower, but it’s hard to shake it’s history name. With only two days in Chicago, a must-see is The Willis Tower; one of the world’s most impressive skyscrapers! You’re able to visit the Skydeck on the 103rd floor where you can step out onto a glass-bottomed box that extends four feet from the building onto ‘The Ledge.’ Heads up to anyone with acrophobia: this might not be your cup of tea. You’ll find yourself staring at the ground below from a heart-thumping height of nearly 1,350 feet! But for everyone else, enjoy the sweeping panoramic views of Chicago that stretch across four states on a clear day.

chicago architectural river tours

Chicago Riverwalk

Make your way to the riverbank for some of the best views in Chicago. This pedestrian walkway is known as the Chicago Riverwalk. It’s a lively and picturesque pathway that runs along the south bank of the Chicago River, right through the heart of downtown. The Riverwalk offers a connected path from the lakefront to the center of the city, featuring beautifully landscaped areas, paths, and places to sit and relax away from the city noise. Along the Riverwalk, there are various attractions, including eateries, bars, and public art, making it a favorite spot for both locals and visitors. It’s a great place to enjoy views of the river and admire Chicago’s impressive architecture.

It’s quite peaceful by the river and fun fact: on St. Patrick’s Day, Chicago celebrates by turning the river a bright, festive green, creating a dazzling sight for the locals.

Visit the Art Institute of Chicago wiht 48 hours in chicago

With 48 Hours in Chicago, you can visit The Art Institute

The Art Institute of Chicago is famous worldwide for its incredible collection of art. You can see paintings by Van Gogh, Seurat, and Monet, to name just a few. Make sure to check out the detailed Thorne Miniature Rooms and the beautiful Chagall stained glass windows. It’s a lovely place for anyone who enjoys art and history. Before visiting, check the latest hours and admission fees on their website here. The museum offers free admission to Illinois residents on certain days, and children under 14 always enter for free.

2 Days in Chicago: Hidden Gems & Insider Secrets

If you’re gearing up for a 2-day adventure in Chicago, you likely have a few questions on how to make the most of your 48-hour Chicago itinerary. Here’s the inside scoop on what to know before you go.

Why should I visit Chicago?

Chicago is a bustling city known for its stunning architecture, rich history, and vibrant cultural scene. From world-class museums and parks to some of the best food in the U.S., like deep-dish pizza and Chicago-style hot dogs, the city offers a dynamic mix of attractions and experiences.

What’s the best way to get around Chicago?

The best way to navigate Chicago is by using public transportation. The ‘L’ train system covers most of the city and suburbs. Busses are also convenient, and apps like Uber and Lyft are widely available. If you’re staying downtown, you’ll find that it’s also very walkable.

What are the most important neighborhoods to visit?

  • The Loop: The heart of Chicago’s downtown, known for its iconic skyline and the Art Institute of Chicago. This is the overall downtown business district.
  • River North: A trendy and pedestrian-friendly area built around the river, known for its art galleries, nightlife, and dining scene.
  • Wicker Park: Great for vintage shops, hipster cafes, and vibrant murals.
  • Lincoln Park: Ideal for those looking for green spaces, and don’t miss the free-entry Lincoln Park Zoo.

What’s the general vibe of each neighborhood?

  • The Loop: Energetic and bustling, it’s the hub of business and tourism.
  • River North: Artsy and upscale, with a splash of the avant-garde.
  • Wicker Park: Bohemian and youthful, a place to see and be seen.
  • Lincoln Park: Leafy and affluent, it offers tranquility close to the lakeside.

Can you recommend a hidden gem in The Loop?

Beyond the skyscrapers and the Bean, find the Chicago Cultural Center. It’s a very cool historic landmark that offers free public events and beautiful interior designs, including an amazing stained-glass dome.

Any insider secrets for dining in Wicker Park?

Skip the main drags and check out the tucked-away Milk & Honey Cafe for some of the best brunches in the area, without the usual wait.

What’s an unusual activity to do in River North?

Want something really different? Visit the International Museum of Surgical Science. Not your typical museum, it features intriguing surgical instruments and medical oddities.

What are some other off-the-beaten-path attractions?

  • The Magic Hedge: An urban bird sanctuary that’s a haven for migrating birds and a peaceful spot for nature lovers.
  • The Bahá’í House of Worship: Just north of the city in Wilmette, this stunning temple offers a unique spiritual and architectural experience.
  • Pullman National Monument: Explore America’s first planned industrial town which offers a deep dive into social history and architecture.

What’s one thing I should make sure to pack?

Definitely bring comfortable shoes. Chicago’s best explored on foot, and you’ll be walking a lot. If it’s winter, bring very warm clothes that are water and wind-proof. You might need a scarf, hat, gloves and boots – it gets very very cold! Here are great things to do when visiting Chicago in winter.

With these insights, your 48 hours in Chicago will be filled with not just the sights but the spirit of this iconic city. Even with just 2 days in this great city, you’re able to get a taste of its eclectic mix of art, food, and architecture. Hopefully, these activities will help you experience the heart of the city and leave you longing for your next visit. From the peacefulness of Millennium Park,  to a vibrant night on a rooftop deck, Chicago has something for every traveler. Enjoy your visit to the Windy City!

If you’re headed to New York you may enjoy: 5 Things to see in Times Square, New York

If you’re headed to London you may enjoy: 48 Hours in London

How would YOU spend 48 hours in Chicago?

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About The Author


I’m a travel and health writer, digital brand consultant, breast cancer survivor, and supermom to two boys! I keep it real and share stories of raising an active family, life after a cancer diagnosis, and family travels around the world! Each story is shared with my dry, and sometimes naughty sense of humor.

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