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Chicago 3-Day Itinerary

Chicago

three days // 18 activities

🌆 Explore Chicago in 3 Days 🍕🎨
Get ready to immerse yourself in the vibrant culture and delicious food of Chicago with this 3-day itinerary. From iconic landmarks like the Buckingham Fountain and Cloud Gate to the world-renowned Art Institute of Chicago, this guide will take you through the best of the city's arts and culinary scene.

Indulge in deep dish pizza at Pleasant House Pub, marvel at the marine life at Shedd Aquarium, and stroll along the scenic Riverwalk. With this itinerary, you'll make the most of your time in the Windy City! 🏙️🍔

Don't miss out on the diverse art and culture Chicago has to offer, from the Museum Campus to the Chicago Cultural Center. Get ready for an unforgettable trip!


Here are all our tips for a perfect itinerary of Chicago in three days!

Day 1

Places visited: 360 CHICAGO, The Art Institute of Chicago, Buckingham Fountain, Museum Campus, Field Museum

Where to eat: Colazione presso 360 CHICAGO, Cena presso Pleasant House Pub

1 09:00

Morning

360 CHICAGO

Visit time: 1.5 hours

Experience breathtaking views of Chicago from 360 CHICAGO!



Hey there! Looking for an amazing view of Chicago? Look no further than 360 CHICAGO! With its 360-degree panoramic views of the city and the lake, this attraction is a must-visit. Whether it's a sunny day or the clouds are high, you'll be in awe of the stunning vistas.

Not only can you enjoy the breathtaking scenery, but you can also sip on a drink while taking in the skyline. For the adventurous souls, you can even experience the thrill of stepping into glass enclosures that extend outwards, giving you the sensation of falling into the void from the 98th floor. Talk about an adrenaline rush!

Make sure to book your tickets in advance to secure your spot. And don't worry about the weather, as the friendly staff at 360 CHICAGO will allow you to change your date and time if the visibility is affected. Trust me, it's worth the wait!

Oh, and don't forget to try the TILT experience, where you'll tilt out over the city for an even more exhilarating adventure. It's an additional $9 per person, but totally worth it!

So, what are you waiting for? Head over to 360 CHICAGO and prepare to be amazed!

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360 CHICAGO
2 10:00

Morning

The Art Institute of Chicago

Visit time: 2 hours

Discover the wonders of Art Institute of Chicago!



Hey there! Looking for an amazing museum experience? Look no further than the Art Institute of Chicago! With its beautiful structure and extensive collection, this museum is a must-visit attraction. Get ready to be amazed by the sought-after artworks it houses.

Make sure to grab a map of the most interesting pieces before you explore, as the museum is immense. And don't worry, there's a bar inside where you can enjoy some delicious food and hot or cold beverages. Just remember to consume them in the designated dining area, not among the artworks.

From the spectacular Impressionist galleries to the captivating works of Renoir, Van Gogh, and Rembrandt, this museum offers a curated collection that will leave you in awe. The spacious exhibition spaces ensure that the artworks are well-displayed, allowing you to fully appreciate their beauty.

Don't miss out on this unforgettable experience! Plan your visit to the Art Institute of Chicago today.

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The Art Institute of Chicago
3 11:30

Morning

Buckingham Fountain

Visit time: 1.5 hours

Be amazed by the powerful water jets of Buckingham Fountain!



Hey there! Looking for a stunning attraction in Chicago? Look no further than the Buckingham Fountain! This large fountain, located in a beautiful green complex, will leave you in awe with its multiple levels of water jets. Whether you visit during the day or at night, you'll be captivated by its decorative beauty and mesmerizing light shows against the backdrop of the city's modern skyline. Don't forget to explore the well-maintained surrounding gardens too!

With its powerful central jet reaching over 20 meters in height, the Buckingham Fountain offers a spectacular view that you can't miss. Surrounded by impressive skyscrapers on one side and Lake Michigan on the other, it's the perfect spot for a break. Keep an eye out for exciting musical events that often take place in this area!

So, what are you waiting for? Grab your camera and head to the Buckingham Fountain for an unforgettable experience!

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Buckingham Fountain
4 15:00

Afternoon

Museum Campus

Visit time: 2 hours

Discover a world of wonders at Museum Campus!



Hey there! Looking for a museum adventure? Look no further than Museum Campus in Chicago. With its diverse collection of exhibits, there's something for everyone to enjoy. Explore the fascinating history of our planet at the natural history museum, dive into the depths of the ocean at the aquarium, and reach for the stars at the planetarium.

But what sets Museum Campus apart is its innovative and engaging approach to showcasing artifacts. No dusty display cases here! Instead, you'll find immersive thematic journeys that will stimulate your curiosity and leave you wanting more. From ancient civilizations to Native American cultures, there's a world of wonders to discover.

Don't miss the highlights of the museum, including the stunning collection of ancient vases and the captivating exhibition dedicated to Leonardo da Vinci. These iconic pieces are sure to leave you in awe.

So, whether you're a history buff, a nature enthusiast, or simply looking for a fun day out, Museum Campus is the place to be. Grab your friends and family and embark on an unforgettable adventure!

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Museum Campus
5 17:00

Afternoon

Field Museum

Visit time: 2 hours

Discover the wonders of natural history at the Field Museum!



Hey there! Looking for an amazing museum experience? Look no further than the Field Museum in Chicago. This museum of natural history will leave you in awe with its vast collection and fascinating exhibits. Spend a day exploring everything it has to offer!

One of the highlights is the spectacular Dinosaur Hall, where you can marvel at the ancient giants that once roamed the Earth. But that's not all! The museum also showcases the evolution of life, animal species, Pacific Islands, precious gemstones, cultivated plants, and much more.

Don't miss the Egyptian section and the Native American exhibits, which are truly captivating. And of course, the star of the museum is Sue, the most extensive and well-preserved T-Rex specimen. Seeing her skull up close is an emotional experience, knowing it has survived for over 60 million years.

So, if you're in Chicago, make sure to visit the Field Museum. It's a must-see attraction that will leave you amazed!

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Field Museum
6 19:00

Evening

Pleasant House Pub

Visit time: 1 hours

Try the delicious steak and ale pie!



Hey friend, have you ever tried a steak and ale pie? Well, I had the most amazing one at Pleasant House Pub in Chicago. It might not be exactly like the one I had in London, but it was still delicious. The meat was more like a beef stew, but trust me, it's worth a try. Besides the food, the service was great and I really enjoyed the atmosphere. You should definitely visit this place and give their steak and ale pie a chance!

And that's not all, they also have a wonderful chicken balti pie with a fantastic flavor. Pair it with a Guinness and you're in for a treat. This place is perfect for a small group of friends. I'll definitely be going back!

Oh, and did I mention they have a brunch menu? I tried their chicken and Scotch egg pie and it was really good, especially considering the price. The service and atmosphere were fantastic as well. I can't wait to go back and try more of their delicious dishes!

Pleasant House Pub is a small but exceptional British pub/restaurant in Chicago. They even serve Cask Ale, which is fantastic. The food is great, and they even have a vegan option, although it could be a bit more traditional. But what really impressed me was their delivery service. They accommodated my special requests and the food arrived in perfect condition, including the fries. They were quick and efficient. I've attached a photo of my meal to show you the amazing fried egg I requested. Next time I'm in town, I'll definitely visit the actual pub. Can't wait!

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Pleasant House Pub

Day 2

Places visited: Grant Park, Ping Tom Memorial Park, Skydeck Chicago

Where to eat: Colazione presso Sleep Walk Chocolateria & Cafe, Cena presso S.K.Y.

1 09:00

Morning

Sleep Walk Chocolateria & Cafe

Visit time: 1 hours

Delicious coffee and chocolate treats!



Looking for a cozy spot to enjoy some delicious coffee and chocolate treats? Look no further than Sleep Walk Chocolateria & Cafe in Chicago! This charming cafe offers a wide selection of chocolate and coffee-based beverages, as well as a great variety of food options. The moka and the lemon-blueberry focaccina are highly recommended by satisfied customers.

One of the standout features of Sleep Walk Chocolateria & Cafe is their consistently perfect coffee. No matter what you order, you can expect a rich and flavorful cup of coffee served at the perfect temperature. The friendly staff and convenient location make it a great place to grab a quick drink to go.

If you're feeling adventurous, be sure to try the Dolor de Oro, a deliciously spiced coffee and chocolate beverage. The friendly and consistent customer service is also worth mentioning.

The only downside is that seating is limited, so it's not ideal for long stays. However, the friendly staff and cozy atmosphere more than make up for it. Don't miss out on this delightful cafe experience!

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Sleep Walk Chocolateria & Cafe
2 10:00

Morning

Grant Park

Visit time: 1.5 hours

Experience the breathtaking beauty of Grant Park!



Hey there! Looking for a fantastic outdoor experience in Chicago? Look no further than Grant Park! This meticulously maintained garden offers stunning views of the lake and features a beautiful fountain that is a must-see, especially at night when it lights up in various colors. Whether you're taking a leisurely stroll or simply enjoying the fresh air, Grant Park is the perfect place to unwind and connect with nature.

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Grant Park
3 11:30

Morning

Shedd Aquarium

Visit time: 2 hours

Dive into the spectacular underwater world!



Hey, have you ever wanted to explore the wonders of the underwater world? Look no further than the Shedd Aquarium in Chicago! This amazing aquarium brings the aquatic environments of the world to life, from freshwater to the sea and oceans. You'll be amazed by the variety of amphibians, reptiles, birds, and of course, fish species on display.

One of the highlights is the dolphin tank, where you can spend hours watching these magnificent creatures swim gracefully. The museum is well-organized, and I highly recommend purchasing the City pass to save money and skip the long entrance lines, especially on weekends.

Don't miss the opportunity to touch the small stingrays in one of the tanks, it's a truly unique experience! Whether you're a passionate fisherman or simply love marine nature, this is the place for you. So, grab your camera and dive into the spectacular underwater world at the Shedd Aquarium!

Arts

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Shedd Aquarium
4 15:00

Afternoon

Ping Tom Memorial Park

Visit time: 1.5 hours

Discover a hidden gem in Chicago's Chinatown!



Looking for a peaceful escape from the city? Look no further than Ping Tom Memorial Park, a hidden treasure nestled in Chinatown. With its stunning views of the city skyline and a variety of amenities, this park is a must-visit attraction.

Take a stroll along the riverfront and enjoy the beautiful bamboo gardens. There are plenty of benches along the river trail where you can relax and take in the scenery. For families, there's a playground for the little ones to enjoy.

Don't miss the opportunity to rent a kayak and explore the river. Fishing enthusiasts will also find a fishing pier to cast their lines. And if you're in the mood for a picnic, there are ample picnic areas available.

With its tranquil atmosphere and picturesque surroundings, Ping Tom Memorial Park is the perfect place to unwind and enjoy the great outdoors. Come and discover this hidden gem in Chicago's Chinatown!

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Ping Tom Memorial Park
5 17:00

Afternoon

Skydeck Chicago

Visit time: 1.5 hours

Experience the thrill of the Skydeck!



Looking for an unforgettable experience in Chicago? Look no further than the Skydeck! Located on the 103rd floor of the tallest building in the city, this attraction offers breathtaking views and a unique opportunity to step out onto a glass balcony suspended in mid-air.

With 90 seconds to capture the perfect photo, you'll want to make the most of your time. Don't worry about the cost, as the experience is well worth it. While the prices may seem high, remember that you're getting a once-in-a-lifetime chance to see the city from a whole new perspective.

Before heading up, take some time to explore the exhibition that prepares you for the ascent. Once you step into the elevator, you'll be whisked up 103 floors in just one minute. The view from the top is truly spectacular!

Whether you're an adrenaline junkie or simply looking for a unique experience, the Skydeck is a must-visit attraction in Chicago. Don't miss out on this thrilling adventure!

Arts

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Skydeck Chicago
6 19:00

Evening

S.K.Y.

Visit time: 2 hours

Experience the incredible cuisine at S.K.Y.!



Looking for a perfect place to celebrate a special occasion? Look no further than S.K.Y.! The staff is incredibly friendly and the food is absolutely delicious. The tasting menu is a must-try, with every dish being exceptional. Don't forget to try their amazing cocktails too! The service is attentive and charming, although it can be a bit slow at times. But trust me, the food is worth the wait!

The menu offers a variety of small plates that are perfect for sharing with friends. And if you're looking for recommendations, the spaghetti alle vongole and tiramisu are simply spectacular. The restaurant is located in the heart of Chicago, just a short Uber ride away. So why wait? Come and experience the authentic and mouthwatering cuisine at S.K.Y.!

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S.K.Y.

Day 3

Places visited: Riverwalk, Chicago Cultural Center, Garfield Park Conservatory, Cloud Gate

Where to eat: Colazione presso TE'AMO Boba Bar, Cena presso Kristoffer's Cafe & Bakery

1 09:00

Morning

TE'AMO Boba Bar

Visit time: 1 hours

Delicious Bubble Tea and Desserts!



Looking for a cute Bubble Tea shop with a variety of flavors? Look no further than TE'AMO Boba Bar in Chicago! With their delicious drinks and desserts, you won't be disappointed. The milk tea and strawberry Dalgona drinks are must-tries, and don't forget to grab some mochi donuts. The packaging and presentation of the drinks are top-notch, making it a great spot for Instagram-worthy photos. The atmosphere inside is lively, although it can get busy. The friendly staff and fantastic drinks create a welcoming vibe. Just be mindful of the small portion sizes. Located in Chinatown, this place is definitely worth a visit!

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TE'AMO Boba Bar
2 10:00

Morning

Riverwalk

Visit time: 1.5 hours

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Experience the enchanting Riverwalk!



Hey there! Looking for a magical experience in Chicago? Look no further than the Riverwalk! Whether you visit during the day or at night, this place will leave you in awe. The shimmering lights, passing boats, and pleasant stroll along the river will captivate you. And guess what? You can even go kayaking and witness the beauty from a different perspective. Don't miss the breathtaking sunset and the illuminated view after dark!

But that's not all! The Riverwalk is not just about the scenery; it's also a hub of fantastic dining options. Indulge in delicious food and drinks at the various open-air restaurants and bars. Just remember, they close at 11 pm, so plan your dinner accordingly. Trust me, this is a must-do activity in Chicago!

During your visit, make sure to admire the picturesque aqua-green river and the towering skyscrapers that seem to emerge from the water. And if you're lucky enough to be here in the summer, you might even catch a glimpse of rowing teams practicing on the river. It's truly a sight to behold!

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Riverwalk
3 11:30

Morning

Chicago Cultural Center

Visit time: 1.5 hours

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Discover the stunning Tiffany dome and more at this cultural gem!



Hey there! Looking for a cultural adventure in Chicago? Look no further than the Chicago Cultural Center. With its magnificent Tiffany dome and beautifully curated exhibits, this center is a must-visit for art enthusiasts and history buffs alike.

One of the highlights is the stunning Tiffany dome located on the first floor. Its intricate design and vibrant colors will leave you in awe. Make sure to spend some time in the room where it is housed, as it is truly a sight to behold.

But that's not all! The center also offers a fascinating exhibition that sheds light on the perspective of U.S. veterans through photos, artifacts, and brochures. It's a unique opportunity to gain insight into the wars fought by the U.S. army.

Don't miss out on this cultural gem in Chicago. Whether you're a fan of art, history, or simply looking for a peaceful spot to relax, the Chicago Cultural Center has something for everyone. Plan your visit today!

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Chicago Cultural Center
4 15:00

Afternoon

Garfield Park Conservatory

Visit time: 2 hours

Escape to a botanical paradise in Chicago!



Looking for a relaxing and beautiful escape from the city? Look no further than the Garfield Park Conservatory in Chicago! This stunning botanical park is the perfect place to unwind and immerse yourself in nature.

With its lush greenery and vibrant flowers, the conservatory offers a peaceful and rejuvenating experience. Take a leisurely stroll through the various exhibits and be amazed by the diverse plant collections.

One of the highlights is the Winter Garden, adorned with silver and red holiday decorations, bringing warmth to Chicago's cold winters. Don't miss the historic staircase and the fern room, although it's not accessible to visitors.

Planning a visit is easy, with free parking and convenient access to public transportation. Just make sure to check their website for reservations, as they are closed on Mondays and Tuesdays.

Whether you're a nature lover or simply seeking a tranquil retreat, the Garfield Park Conservatory is a must-visit attraction in Chicago. Don't forget to stop by the gift shop for unique souvenirs!

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Garfield Park Conservatory
5 17:00

Afternoon

Cloud Gate

Visit time: 1.5 hours

Discover the mesmerizing Cloud Gate!



Hey there! Have you heard about Cloud Gate, also known as The Bean? It's a stunning stainless steel sculpture located in Chicago, Illinois. Created by the British-Indian artist Anish Kapoor, this artwork consists of 168 welded stainless steel plates, seamlessly joined together.

What makes it truly unique is its ability to perfectly reflect the city's skyline, earning it the title of one of the most photographed places ever. Trust me, you'll be amazed by its beauty!

Imagine standing in front of The Bean early in the morning, with no one around, and witnessing the breathtaking spectacle of the city's skyscrapers merging with the sculpture. It's an experience you won't forget!

So, don't miss out on this must-see attraction in Millennium Park. Get ready to capture some incredible photos and immerse yourself in the artistic wonders of Cloud Gate!

Arts

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Cloud Gate
6 19:00

Evening

Kristoffer's Cafe & Bakery

Visit time: 1 hours

Try the delicious Tres Leches cake!



Looking for a cozy and affordable cafe in Chicago? Look no further than Kristoffer's Cafe & Bakery! With excellent coffee and mouthwatering croissants, this place is a must-visit. The caramel cake is fantastic, and the coconut cake is good, but the real star is the Tres Leches cake. Light, airy, and not too sweet, it's simply delicious. The chocolate flan is also a crowd favorite, with its dense texture and deep chocolate flavor. And let's not forget the friendly staff, who make you feel right at home. Don't miss out on trying their other flavors of Tres Leches cake too. You won't be disappointed!

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Kristoffer's Cafe & Bakery

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