CHICAGO: What to see, and do

Chicago, IL

Did you know that Chicago is home to the world's first ever Ferris wheel! It was built in 1893 for the World's Columbian Exposition and even predates the iconic Navy Pier Ferris wheel that stands today?

I lived for six months in this city and I loved every moment. There's so much things to do and see that you'll wish you could live here.

TIP: The city is incredibly walkable, and getting around is a very easy with the convenient train and bus system. To make your exploring even smoother, grab a Ventra card at any metro station. It's a reloadable pass that lets you use the trains and buses with ease, saving you time and money! Whether you're a Google Maps whiz or prefer a dedicated app, you can easily find real-time train and bus schedules.

📍 Must see's in Chicago

Chicago is a vibrant city with something for everyone. Here are some of the must-see sights.

Cloud Gate

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The iconic Cloud Gate, also known as "The Bean" Located in the Millenium park is this giant reflective sculpture, is a popular spot for photos and people-watching

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The Art Institute of Chicago

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The beautiful Art Institute of Chicago is home to an impressive collection art. It has a lot of interesting exhibits that rotate throughout the year.

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Skydeck Chicago

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On a clear day, you might even peek into 4 states! This glass balcony sticks out from the building, 103 stories up! It's wild (and totally safe). Also you can learn about Chicago's history and architecture through engaging exhibits. TIP: Purchase tickets online in advance to skip the lines, especially during peak hours. Consider the time of day for your visit. Daytime offers stunning views, while nighttime provides a magical cityscape panorama.

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Riverwalk

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Chicago's got this awesome path called the Riverwalk, and it's basically a hidden gem. It's right along the river downtown, so you can escape the city noise for a sec and just relax. What's cool about it: you can walk by those giant buildings. There's cool sculptures and stuff all along the way to check out. Grab a bite or a drink at all the restaurants and cafes with river views. You can rent a kayak or paddleboat for a unique city tour. And last but not least when the sun sets, the Riverwalk turns into a party spot with bars and restaurants ready to keep the good times going.

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Chicago Architecture River Cruise

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Want epic pics of Chicago's famous buildings without all the walking? Hop on a Chicago Architecture River Cruise! It's basically a floating tour guide that shows off the city's coolest skyscrapers. Expert local guides tell you all about all the cool stories behind the buildings.

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Navy Pier

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Navy Pier is a fun spot to explore, with shops, restaurants, games, beautiful lakeside location and entertainment options for everyone. Catch the free fireworks displays on most Saturdays during the summer. It's a magical way to end your day at Navy Pier! TIP: The ride is a little pricey but the views are very worthy. If you'd like to have a ride you can make use of your city pass for this attraction.

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Pro Tip: I highly recommend purchasing a city pass to get the more out of Chicago!

Chicago CityPASS

es.citypass.com

🍽 Where to eat

I'm honestly a grab-on-the-go person while talking about food but I'll definitely plan to visit any (or all) of these places.

Portillo's & Barnelli's Chicago

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Portillo's is a beloved Chicago-style restaurant chain known for its mouthwatering Italian beef sandwiches, hot dogs, and chocolate cake. Portillo's has become a culinary institution, attracting both locals and tourists alike.

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Lou Malnati's Pizzeria

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If you're in Chicago you have to try deep dish pizza, there're so many places to go but out of all of them Lou Malnati's is my favorite place.

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Starbucks Reserve Roastery Chicago

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The world's largest Starbucks is a five-story experience in Chicago! This isn't just a coffee shop, it's an immersive coffee wonderland. Witness the roasting process, explore unique coffee creations, and indulge in fresh-baked treats. TIP: While lines can form in the morning, they tend to move quickly. Don't let a short wait deter you from this unforgettable experience.

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RAMEN-SAN Deluxe

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This is not a "classic" Chicago spot but is one of my very favorites. This hip joint isn't your average ramen shop – it's a fusion fiesta with delicious broths, creative toppings, and an awesome vibe. Their menu is unique and my favorite part is the chill atmosphere and the friendly staff.

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🍸 Bars and roof tops

The Green Mill

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Whether you're a die-hard jazz fan or simply curious about Chicago's cultural scene, the Green Mill is a must-visit. It's a chance to experience live music in a historic setting. TIP: This is a cash only bar and you can check who's playing on their website. I highly recommend arriving early specially on weekends

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Check who's playing here

greenmilljazz.com

Cindy's Rooftop

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This rooftop bar offers stunning views of Millennium Park, Lake Michigan, and the city skyline. They also have a wide selection of cocktails, beers, and wines, as well as a seasonal menu of small plates.

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LH Rooftop

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Three levels of hotel rooftop drinking and dining with indoor/outdoor seats and amazing views. Located on the 22nd floor of the LondonHouse Chicago, this rooftop bar offers 360-degree views of the city.

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Aire Rooftop Bar Chicago

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This rooftop bar is located on the 24th floor of the Hyatt Centric The Loop Chicago and offers stunning views of the city skyline and the Chicago River.

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Kingston Mines

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A legendary blues bar on Chicago's North Side. They've been hosting top blues acts since the 1960s and offer a true dive bar experience.

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The Violet Hour

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This speakeasy-style bar is hidden behind a fake flower shop and requires a reservation to enter. Step back in time with their vintage cocktails and elegant atmosphere.

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LondonHouse Chicago, Curio Collection by Hilton

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With its elegant design and unparalleled vistas, the London House Rooftop provides a memorable experience in the heart of downtown Chicago.

Check Prices

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💃🏽 Fiesta latina

Esco

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My very favorite bar/club you can go to Komo, the restaurant downstairs, have a drink, something to eat and then head upstairs to party at the rithm of latin music. LOVE, LOVE, LOVE this place <3

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The Mine Chicago

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This is another favorite spor of mine. If you're looking for a fun and energetic night out in Chicago, The Mine is the place to be. They offer three distinct rooms, each featuring a different DJ and vibe. They have DJs spinning Latin, Top 40, and more all night long, keeping the party going until the early hours.

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Carnivale

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This isn't just a nightclub, it's a Latin American restaurant with a vibrant atmosphere. They often feature live music from Latin artists, professional dancers, and DJs spinning a mix of Latin beats. It's a great place to enjoy a delicious meal, drinks, and some Latin entertainment.

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🌆 Neighborhoods

Chicago is a city bursting with diverse neighborhoods, each with its own unique character and charm. Here are a few neighborhoods you should consider exploring

West Loop

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A trendy neighborhood known for its upscale restaurants, art galleries, and trendy shops.

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Wicker Park

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A hipster haven with a mix of vintage stores, independent boutiques, art galleries, and trendy bars and restaurants.

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Lincoln Park

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A family-friendly neighborhood with a zoo, a lakefront park, and a variety of shops and restaurants.

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Gold Coast

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A chic neighborhood known for its high-end shops, luxury hotels, and upscale restaurants. Magnificent Mile, a famous shopping street, is located in this neighborhood.

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Lake View

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A lively neighborhood with a mix of bars, restaurants, shops, and theaters. It's also home to Wrigley Field, the historic baseball stadium of the Chicago Cubs.

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Chinatown

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The second-oldest Chinatown in North America, it's a great place to experience Chinese culture, with authentic restaurants, shops, and temples.

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Pilsen

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A vibrant Latino neighborhood known for its colorful murals, art galleries, and traditional Mexican restaurants. As a Mexican I can tell you that I would go there to cure my homesickness, food is really good!

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🏖 Beaches

This city really have it ALL! While they have a long winter, summer is an amazing opportunity to enjoy the stunning 26 miles of shoreline along Lake Michigan. For swimming, sunbathing, relaxing, and enjoying watersports. Here's a list of some popular beaches in Chicago

North Avenue Beach

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One of the most popular beaches in Chicago, North Avenue Beach offers a variety of amenities including volleyball courts, a play area, concession stands, and lifeguards. It's also a popular spot for kayaking, paddleboarding, and jet skiing.

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Oak Street Beach

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This upscale beach is known for its white sand and proximity to trendy shops and restaurants on Oak Street. Offers stunning views of Lake Michigan and the city skyline.

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Ohio Street Beach

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Located just north of Navy Pier, Ohio Street Beach is a popular spot for swimming and sunbathing. It also offers stunning views of Lake Michigan and the city skyline. There are volleyball courts and a playground available as well.

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Montrose Beach

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Montrose Beach is a popular spot for swimming, sunbathing, and picnicking. It also offers a variety of amenities including volleyball courts, a running/walking path, a bird sanctuary, and a dog beach.

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Foster Beach

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Foster Beach is a great spot for families with young children. It has a shallow shoreline and a variety of amenities including a playground, concession stands, and restrooms.

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Ready to explore the Windy City? This guide has packed in all my favorite spots, the must-sees and hidden gems to make your Chicago trip unforgettable. 

I hope this guide is useful for planning your visit to Chicago. If you like this guide I invite you to check some of my other guides, schedule a consultation, or ask for a custom-made itinerary. I'd be happy to help you plan your trip!

Thank you for reading, follow me on Instagram @anacrisabroad! There you'll find even more travel inspiration, insider tips, and stunning photos to fuel your wanderlust. Plus, I'd love to hear from you! Feel free to DM me with any questions, feedback, or just to say hi!