10 Ways to Spend One Day in Chicago

Hey there fellow travelers and welcome to my post where we will cover 10 ways to spend one day in Chicago. Now, we all know the joys that travel can bring, from visiting far off places, experiencing different cultures and of course, all the new foods. But there is also a downside, – that dreaded day to ‘waste’ in a city whilst waiting for a midnight flight.

So if you are like me (as I live in Australia, all outgoing flights seems to leave late at night), there has been many a day where you need to find something to do that is enjoyable, but doesn’t take too much time – or cost too much money. So if you have a long layover or a day to kill in Chicago, here are 10 things you can do to pass the time in an enjoyable way.

Let’s check them out…

Ways to Spend One Day in Chicago

A vibrant mix of American cultural and architectural prowess, Chicago is a melting pot of arts, with its world-class museums like the Art Institute of Chicago, a bustling music scene echoing with blues and jazz and diverse culinary delights ranging from deep-dish pizza to gourmet cuisines. Whether you’re strolling along the Magnificent Mile, taking an architectural river cruise or reveling in a summer festival by the lake, Chicago promises an enthralling urban adventure at every corner.

1. Start Your Day with a Breakfast at a Local Diner

Chicago is a city that takes its breakfast seriously and there are plenty of diners and cafes that offer a wide range of breakfast options to start your day off right. Here are some of the best places to grab a delicious breakfast in Chicago:

Lou Mitchell’s

Lou Mitchell’s has been serving breakfast to Chicagoans since 1923. This classic diner is known for its hearty breakfasts and friendly service with a menu that features classic breakfast dishes like pancakes, waffles, omelets and eggs benedict. Oh, and don’t forget to try their famous homemade donuts!

The Bongo Room

The Bongo Room is a popular breakfast spot with locations in Wicker Park, Andersonville and the South Loop. Their menu features creative twists on classic breakfast dishes like pancakes, French toast and eggs benedict. Try their signature pancake flight for a taste of three different flavors.

Yolk

Yolk has several locations throughout the city and is known for its creative breakfast dishes. Their menu features items like red velvet French toast, breakfast mac and cheese and a variety of eggs benedict options. They also offer gluten-free and vegetarian options as well.

Wildberry Pancakes and Cafe

Wildberry Pancakes and Cafe is a must-visit for pancake lovers with a menu that features a wide range of pancake flavors like Oreo, caramel apple and cinnamon roll. They also offer other breakfast dishes such as omelets, skillets and crepes too.

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2. Visit the Art Institute of Chicago

If you’re an art lover, the Art Institute of Chicago is a must-visit attraction. This world-renowned museum is home to an impressive collection of art from around the world, including works by famous artists like Vincent van Gogh, Claude Monet and Georgia O’Keeffe.

One of the museum’s most famous pieces is “The Bedroom” by Vincent van Gogh. This iconic painting is just one of many by the Dutch artist that can be found at the Art Institute of Chicago and you’ll also want to check out his famous self-portrait while you’re there. Another highlight of the museum is the “Stack of Wheat” series by Claude Monet.

In addition to these famous pieces, the Art Institute of Chicago has a vast collection of art from around the world including African, Asian and European art. You can easily spend hours exploring the museum’s galleries and admiring the stunning works on display.

The Art Institute of Chicago is open every day except Thanksgiving, Christmas, and New Year’s Day. Admission prices vary depending on age and residency, but there are several free admission days throughout the year.

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3. Take a Stroll in Millennium Park

If you’re looking for a relaxing way to spend your day in Chicago, taking a stroll through Millennium Park is a must. With 25 acres of beautiful landscape, public art and architecture, the park is a popular destination for both locals and tourists alike. Here are a few highlights to check out during your stroll:

The Bean

One of the most iconic landmarks in Chicago, Cloud Gate (also known as “The Bean”) is a must-see attraction in Millennium Park. Designed by artist Anish Kapoor, the sculpture is made up of 168 stainless steel plates that reflect the city’s skyline and visitors from all angles. Take a selfie or a group photo in front of the bean for a memorable keepsake of your trip.

Crown Fountain

Another popular attraction in Millennium Park is the Crown Fountain. Designed by Spanish artist Jaume Plensa, the fountain features two 50-foot towers that display faces of Chicago residents. The towers periodically spout water from the mouths of the faces, creating a fun and interactive experience for visitors. Don’t forget to bring a change of clothes if you plan on getting wet!

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4. Explore Navy Pier

If you’re looking for a fun-filled day in Chicago, Navy Pier is a must-visit destination. Located on the shores of Lake Michigan, Navy Pier is a hub of entertainment, dining and shopping. Here are some of the top things to do at Navy Pier:

• Ride the Ferris Wheel – The Navy Pier Ferris Wheel is an iconic attraction that offers breathtaking views of the city skyline and Lake Michigan. Standing at 150 feet tall, it’s a thrilling experience that you won’t forget. You can purchase tickets online or at the pier.
• Visit the Chicago Children’s Museum – The Chicago Children’s Museum is a great place to take your kids for an educational and fun experience. With three floors of exhibits, your children will have a blast exploring and learning. Admission fees apply.
• Take a Boat Tour – Navy Pier offers a variety of boat tours that allow you to explore the city from a different perspective. You can choose from architecture tours, sightseeing tours and more. Prices vary depending on the tour.
• Enjoy the Food – Navy Pier has a wide variety of dining options available from fast food to sit-down restaurants. You can try classic Chicago-style hot dogs, deep-dish pizza or seafood at Riva Crab House. There are also plenty of places to grab snacks and treats throughout the pier.
• Experience the Attractions – In addition to the Ferris Wheel and Chicago Children’s Museum, Navy Pier offers other attractions such as the Amazing Chicago Funhouse Maze, the Pepsi Wave Swinger and the Light Tower Ride. Each attraction has its own admission fee.
• Shop for Souvenirs – Navy Pier has a variety of shops where you can find unique souvenirs to take home with you. From Chicago-themed apparel and accessories to handmade crafts and artwork, there’s something for everyone.
• Take a Segway Tour – If you’re looking for a unique way to explore the city, consider taking a Segway tour. You can rent a Segway at Navy Pier and take a guided tour of the city. Prices vary depending on the tour.

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5. Lunch at Chicago’s Famous Pizzerias

If you’re spending one day in Chicago, you can’t leave without trying the city’s famous pizza. Chicago is well-known for its deep-dish and thin crust pizzas,and there are plenty of pizzerias to choose from. Here are some of the most iconic pizzerias in Chicago that you can visit for lunch.

Deep-Dish Pizza

When it comes to deep-dish pizza, Chicago-style is the way to go. Here are some of the best pizzerias in Chicago that serve this iconic pizza:

• Pizzeria Uno: This is the birthplace of deep-dish pizza and has been serving its famous pizza since 1943. The pizza is made with a buttery crust, chunky tomato sauce and lots of cheese. You can choose from a variety of toppings to customize your pizza as well.
• Lou Malnati’s: This pizzeria is known for its buttery crust and sweet tomato sauce. The pizza is loaded with cheese and toppings, making it a filling lunch option.
• Giordano’s: This pizzeria is famous for its stuffed pizza. The pizza has a thick crust and is filled with cheese and toppings. It’s like a pizza and a pie combined.

Thin Crust Pizza

If you prefer a lighter pizza, then Chicago’s thin crust pizza is the way to go. Here are some of the best pizzerias in Chicago that serve this style of pizza:

• Pequod’s Pizza: This pizzeria is known for its caramelized crust. The pizza is thin and crispy and the crust is coated with cheese, giving it a unique flavor.
• Vito & Nick’s: This pizzeria has been serving thin crust pizza since 1946. The pizza is crispy and loaded with toppings and you can choose from a variety of toppings as well.
• Piece Brewery and Pizzeria: This pizzeria is known for its New Haven-style pizza. The pizza has a thin crust and is topped with fresh ingredients. You can choose also from a variety of toppings to customize your pizza.

Book your trip to Chicago here!

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6. Visit the Skydeck

If you’re looking for breathtaking views of Chicago, visiting the Skydeck at Willis Tower is a must-do activity. This iconic attraction offers 360-degree views of the city from 1,353 feet (412 meters) above ground level.

To make the most of your visit, consider going early in the morning or on a weekday to avoid long lines and crowds. You can purchase tickets online in advance to skip the ticket line and save time.

Once you arrive, take the elevator up to the Skydeck and step out onto The Ledge, a glass balcony that extends 4.3 feet (1.3 meters) from the building. It’s a thrilling experience to stand on the glass floor and look down at the city below.

Here are a few tips to keep in mind when visiting the Skydeck:

• Dress appropriately for the weather, as you may be waiting outside in line.
• Consider visiting during off-peak hours to avoid crowds.
• Bring a camera or smartphone to capture the stunning views.
• If you’re afraid of heights, you may want to skip The Ledge.
• Don’t forget to check out the interactive exhibits and gift shop on the Skydeck.

Overall, visiting the Skydeck is an unforgettable experience that you won’t want to miss during your one day in Chicago.

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7. Shop The Magnificent Mile

If you’re a shopping enthusiast, The Magnificent Mile is the place to be. This iconic strip stretches over 13 blocks of prime real estate from the Chicago River to Oak Street Beach and houses over 450 retailers and flagship stores that cater to every style and taste imaginable. Here are some of the best places to shop on The Magnificent Mile:

• Water Tower Place: This historic mall is known for having over 100 stores including American Girl Place, The LEGO Store and Adidas, housed on eight floors. It even has its own live theater.
• 900 North Michigan Shops: This multistory mall features 70 stores on seven levels where you’ll find national brands and unique boutiques.
• The Shops at North Bridge: This shopping center has over 50 stores including Nordstrom, Hugo Bos, and Sephora.
• The Magnificent Mile Association: This association has over 200 members including luxury retailers, hotels and restaurants.
• Oak Street: This upscale shopping destination features high-end boutiques including Hermes, Prada and Giorgio Armani.
• Michigan Avenue: This street is lined with department stores, designer boutiques and flagship stores, including Macy’s, Burberry and Apple.
• Chicago Place: This shopping center has over 50 stores, including The Limited, Victoria’s Secret and Aldo.
• The Shops at the Mart: This shopping center is located inside the Merchandise Mart and features over 30 stores including Bluemercury, Paper Source and LK Bennett.
• Bloomingdale’s: This department store features designer clothing, shoes and accessories from top brands including Gucci, Prada and Saint Laurent.
• Saks Fifth Avenue: This department store features luxury clothing, shoes and accessories from top designers including Chanel, Dior and Valentino.

Whether you’re looking for high-end fashion, unique gifts, or souvenirs, The Magnificent Mile has something for everyone. Don’t forget to take a break and enjoy some of the delicious food and drinks available at the many restaurants and cafes along the way.

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8. Explore Chicago’s Lakefront Trail

Stretching along the glistening shores of Lake Michigan, Chicago’s Lakefront Trail offers both locals and visitors a scenic escape in the heart of the urban sprawl. This 18-mile paved pathway, framed by skyline vistas on one side and vast watery horizons on the other, is a haven for joggers, cyclists and leisurely strollers alike.

The trail seamlessly connects various beaches, parks, gardens, and recreational facilities, making it an ideal route to explore iconic landmarks such as Navy Pier, Lincoln Park Zoo and the Museum Campus. For tourists, the trail offers more than just a picturesque route; it’s a journey through Chicago’s cultural and recreational heart.

Along the way, one might stumble upon charming harbors dotted with boats, green oases like Grant Park with its famed Buckingham Fountain and local eateries serving Chicago’s culinary favorites. Furthermore, strategically placed rental stations provide bikes and equipment for those eager to cover more ground.

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9. Dine at Michelin Star Restaurants

Chicago is a foodie’s paradise and dining at a Michelin-starred restaurant is a must-do experience. Here are some of the best Michelin-starred restaurants in Chicago that you can consider for a memorable dinner.

• Alinea – Alinea is a three-Michelin-starred restaurant in the Lincoln Park neighborhood helmed by Chef Grant Achatz. The restaurant offers a unique and innovative dining experience that is sure to leave you in awe. The menu changes frequently, but you can expect dishes like black truffle explosion, hot potato cold potato, and more.
• Boka – Boka is a one-Michelin-starred restaurant in Lincoln Park, known for its contemporary American cuisine. The restaurant has a warm and inviting atmosphere, making it perfect for a romantic dinner or a night out with friends. The menu features dishes like roasted duck breast, grilled octopus, and more.
• Oriole – Oriole is a two-Michelin-starred restaurant in the West Loop known for its inventive and playful dishes. The restaurant offers a tasting menu that changes frequently but you can expect dishes like foie gras with cherry and pistachio, and more.
• Temporis – Temporis is a two-Michelin-starred restaurant in West Town, known for its modern American cuisine. The restaurant has a cozy and intimate atmosphere, making it perfect for a romantic dinner. The menu features dishes like duck with black garlic and cherry, and more.
• Elizabeth – Elizabeth is a one-Michelin-starred restaurant in Lincoln Square, known for its farm-to-table cuisine. The restaurant offers a tasting menu that changes frequently, but you can expect dishes like roasted beet with goat cheese, and more.

Whether you’re celebrating a special occasion or just want to treat yourself to a memorable dinner, dining at a Michelin-starred restaurant in Chicago is an experience you won’t forget. Be sure to make a reservation in advance, as these restaurants are in high demand.

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10. End Your Day at a Jazz Club

Chicago is known for its vibrant jazz scene and what better way to end your day than by experiencing it firsthand at one of the city’s jazz clubs. Here are some of the best jazz clubs in Chicago to visit:

1. Green Mill Cocktail Lounge: This iconic jazz club has been around since the early 1900s and has hosted some of the biggest names in jazz. The club’s decor is reminiscent of the Prohibition era and it’s a great place to grab a drink and listen to some live music.
2. Andy’s Jazz Club: This club has been around since the 1950s and is a popular spot for both locals and tourists alike. They have live music every night of the week and offer a full menu of food and drinks.
3. Jazz Showcase: This club has been around since 1947 and has hosted some of the biggest names in jazz. They have live music every night of the week and offer a full menu of food and drinks.
4. The Velvet Lounge: This club is located in the historic Bronzeville neighborhood and is known for its intimate setting and great live music. They have live music every night of the week and offer a full menu of food and drinks.

No matter which jazz club you choose to visit, you’re sure to have a great time. Sit back, relax, and let the music transport you to another world.

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Conclusion

There you have it; my top things to do in Chicago in one day. As usual, let me know of your experiences here or if there is anything you think I need to add.

Also, please do not hesitate to comment below if you have any questions, concerns, or corrections or would like me to check anything else out for you.

Until next time.

Have fun

Paul

Traveling Further? Check out these other locations to spend a day in:

• Ways to Spend One Day in New York
• Ways to Spend One Day in Los Angeles
• Ways to Spend One Day in Miami