From marveling at iconic landmarks like The Bean and the historic Tribune Tower to enjoying the city's world-renowned culinary scene, this guide offers practical tips for an unforgettable adventure in the Windy City.

Chicago's bustling neighborhoods and numerous attractions provide a wide range of experiences for all types of travelers. From the historic charm of Millennium Park to the frenetic energy of the Magnificent Mile, the city offers a distinct blend of incredible architecture and cultural attractions. Visitors may explore world-class museums, savor local cuisine, and stroll through lovely parks, all while immersed in the city's rich history.

Millennium Park

One can’t say they have been to Chicago if they haven't visited Millennium Park. The 9.9-hectare park complex is the city’s pride in tourism, featuring various sculpted masterpieces, including the iconic Cloud Gate, commonly known as “The Bean.” Located along the famous Michigan Avenue, the park offers a unique experience compared to a typical city park, as the striking sculpture pieces are well complemented by a wide expanse of greenery. This public park also hosts music shows and concerts at the Jay Pritzker Pavilion, a 4,000 seater music hall situated in the middle of the park.

Just make sure to visit the park at an earlier time to avoid the mid-day crowd and to have a perfect mirror picture at the surface of The Bean!

Chicago Riverwalk

One of the city’s prides is its vibrant Chicago Riverwalk, which runs along a canyon of world-famous architecture and skyscrapers. This two-kilometer riverwalk features various commercial hubs, including hotels, cafes, bars, restaurants, and parks, offering tourists a rich experience.

One of its notable features is the steel bridges that connect pedestrians and vehicles across the river. These bridges, made from recycled parts of demolished buildings, have an iconic, rusty look. This free public walkway is exclusive for all pedestrians and pets who wish to enjoy a trail along the Chicago River’s wide waterways.

Chicago Architecture River Tour

For those who are not a fan of walking, but still want to appreciate the picturesque stretch of the Chicago River, then the Chicago Architecture River Tour is a perfect option. The tour offers a classic boat ride along the waters of the Chicago River. A tour guide option is a must for first-timers as it gives a more cultural involvement to the city, given that the tour guides are well equipped with information about the city’s architecture and history.

The river tour docks are located at the Navy Pier and along the walkways of the Chicago Riverwalk. A river tour ticket may cost around $50, depending on the tour provider. It is highly recommended to take the tour early in the morning to enjoy a vibrant landscape of sun-kissed skyscrapers under the morning sun.

The Magnificent Mile

The Magnificent Mile is the lavish stretch of Michigan Avenue that offers a diverse set of experiences for everyone. From the Neo-Gothic architecture of The Wrigley Building and The Tribune Tower to the wide array of fashion boutiques beneath the tall skyscrapers, Michigan Avenue boasts a quintessential American experience. This part of the city blends history with modern trends, as some of today’s famous retail stores are located in the city’s oldest buildings.

While walking along this part of Michigan Avenue is completely free, it’s advisable to bring an ample amount of money, as it features some of the world’s most luxurious commercial retail brands.

Navy Pier

One of the city’s most famous attractions, Navy Pier is a large entertainment hub on the shoreline of Lake Michigan. Filled with shops, restaurants, bars, and carnival rides, the famous pier is like a top amusement park with a free entrance.

A visit to the Navy Pier isn’t complete without a ride in the Centennial Wheel. The 200-feet high ferris wheel offers a great 360-degree view of Chicago and Lake Michigan. It is highly recommendable to allocate one full day at the Navy Pier due to the wide selection of activities available.

The Art Institute of Chicago

Considered as a big part of American history, the Art Institute of Chicago is a must-visit for art enthusiasts. Have a glimpse of the most iconic masterpieces from world renowned artists such as Vincent van Gogh, Pablo Picasso, and Claude Monet. Its art exhibits also cover historic artifacts and classic furniture.

The Art Institute of Chicago is just a walk away from the Millennium Park, making it a good afternoon option after spending a morning walk near The Bean. A regular adult ticket will cost $32, while a senior ticket for those ages 65 and above will cost $26. Student tickets will also cost $26 while children under 14 years old are free of charge.

Field Museum of Natural History

Also known as The Field Museum, this enormous 103-year old museum is a haven for science nerds. It features an extensive array of specimens, artifacts, fossils, and interactive gadgets. A must-see attraction inside the museum is Sue the T-rex, the largest and most complete discovered T-rex in the world.

It is best to have a taxi going to the museum since it’s far from the other attractions. An adult ticket for a tourist costs $30 while student tickets are at $27.

Make sure to also take a picture of the Agusan Gold Image, the only Philippine artifact in the museum!

Chicago Deep Dish Pizza

No trip to Chicago is complete without indulging in the city's signature deep-dish pizza. Unlike traditional pizzas, which are flat and easily eaten by hand, deep-dish pizza is baked in a deep, round pan, resulting in a thick, buttery crust that rises high along the edges. This unique preparation allows for generous layers of cheese, toppings, and a chunky tomato sauce, creating a hearty meal that requires a fork and knife to eat. The thick, buttery crust is layered with cheese, toppings, and a zesty tomato sauce. The generous portions and comforting layers of cheese and sauce resonate with the Filipino love for rich, savory foods.

Lou Malnati's is considered one of the best spots for this Chicago classic, staying true to the original recipe created in 1943. The communal experience of sharing a large pizza aligns well with Filipino dining traditions, where meals are often enjoyed together.

Chicago-style Hot Dog

The Chicago-style Hot Dog is another iconic dish that embodies the city's culinary spirit. It features an all-beef hot dog topped with yellow mustard, neon green relish, onions, tomato cubes, pickles, and green peppers, all nestled in a poppy seed bun. Surprisingly, ketchup is not included, as it is considered a faux pas in the city’s hot dog culture. This dish offers a unique twist on a familiar food. Filipinos enjoy hot dogs, often incorporating them into various dishes, from street food to festive celebrations. The vibrant toppings on a Chicago-style Hot Dog provide an exciting flavor profile that appeals to adventurous eaters.

Portillo's is a beloved local chain known for their quintessential Chicago dogs that represents the city's culinary culture, featuring an all-beef frankfurter served in a steamed poppy seed bun and topped with a colorful array of ingredients.

Quesadilla, Nachos, and Tacos

Mexican cuisine is known for its rich flavors, vibrant ingredients, and mouth-watering tastes and textures that resonate deeply with Filipino taste buds. A quesadilla is a simple yet satisfying dish made with a tortilla filled with cheese and sometimes other ingredients like meats, vegetables, or beans, then folded and grilled until the cheese is melted and the tortilla is crispy.

Moreveoer, nachos consist of tortilla chips topped with melted cheese, jalapeños, guacamole, sour cream, and various other toppings like ground beef or beans. They are typically served as a shareable appetizer or snack. Lastly, Tacos are made by filling a folded or rolled tortilla with various ingredients, including meats, beans, vegetables, and toppings like salsa, cheese, and avocado.

Taco Maya is a unique restaurant in Chicago that offers a delightful fusion of Mexican cuisine. Known for serving traditional recipes and fresh flavors, it provides a modern Mexican dining experience that caters to everyone in the neighborhood and beyond.

Snacks-on-the-Go

From the Target on La Salle Street in Chicago’s River North to a Costco near your accommodation in Illinois, it is clear that one should visit these staple American superstores to prepare for a robust trip ahead. Even leisure walks in downtown Chicago can be so captivating that you might forget about your hunger. However, there is no need to worry: with the plethora of snacks and access to convenience and superstores, from Nature Valley’s granola bars to Reese’s cups, your energy levels will stay up as you explore Millennium Park or excitedly type away at the American Writers Museum.

Keep yourself warm and comfortable

Undoubtedly, Chicago lives up to its nickname, “The Windy City.” Although there may be some sunlight warming your skin, it’s essential to keep your body temperature regulated by bringing an extra jacket or two. To feel your best while exploring and wandering through the avenues of downtown Chicago, consider warming up with a visit to Paris Baguette near the Chicago Riverwalk for a steaming cup of coffee to cozy up for the day ahead.

Make sure to wear comfortable athletic shoes and outfits that help you feel your best throughout the day, as it’s easy to become fully immersed in the excitement of roaming around Chicago.

Prepare E-Sim and flexible data packages

Google Maps, Waze, and Uber are the trifecta for getting around Chicago’s landmarks. Whether contacting your AirBnB or trying to locate the Chicago Cultural Arts Museum, having a reliable broadband WiFi connection and internet access is essential for reaching your destinations.

Purchasing ‘Simly’ E-Sims that range up to 24GB can save you the hassle of worrying about missed schedules or meet-ups, offering a cost-effective alternative to buying a physical SIM card.

One can’t deny that the diverse and vibrant scenery of the city is truly a unique one, an atmosphere that will be truly appreciated. With its rich history and modern advancements, the city of Chicago ensures a prime American experience for all the tourists from around the world.

Articles by Gabrielle Almirol

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