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Traveling to Chicago: A First-Time Visitors Guide

March 28, 2024 by Karyn Locke

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Chicago is one of the most popular cities (it’s the third largest city in the United States, attracting millions of visitors every year.) Known for its rich history, diverse culture, vibrant nightlife, and iconic architecture, traveling to Chicago is a must, especially if you love big cities. Whether you are looking for a relaxing getaway, a cultural immersion, or an adventurous experience, Chicago has something for everyone. Here’s a quick guide, including information and tips on how to plan your trip to Chicago, what to see and do, and what to expect from the city.



Planning Your Trip

Page Contents

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  • Planning Your Trip
  • Things to See and Do in Chicago
  • What to Expect
  • Traveling to Chicago: In a Nutshell
traveling to chicago - The Bean
The Bean (Cloud Gate) in Chicago. Image Credit: Karyn Locke



Before you travel to Chicago, there are some things you need to consider, such as your budget, your transportation, your accommodation, and your itinerary.

Budget: Chicago is not an inexpensive city to visit, but it is possible to enjoy it without breaking the bank. You can save money by booking your flights and hotels well in advance, using public transportation or ride-sharing services, and taking advantage of free or discounted attractions and events.


Transportation: Chicago has a well-developed public transportation system consisting of buses, trains, and bikes. You can use the Ventra Card to pay for your fares or a Go Chicago Card to get unlimited access to public transportation and some attractions. You can also use ride-sharing services, such as Uber or Lyft, or rent a car if you prefer more flexibility. However, be aware that parking can be expensive and traffic can be (and most likely will be unless it’s four in the morning) congested in the city.


Accommodations: Chicago offers a wide range of accommodation options, from luxury hotels to budget hostels, from downtown skyscrapers to cozy neighborhoods. You can choose your accommodation based on your preferences, your budget, and your location. Some of the most popular areas to stay in Chicago are the Loop, the Magnificent Mile, River North, Lincoln Park, and Wicker Park. You can use online platforms, such as Booking.com, Airbnb, or even Hostelworld, to find and compare your options.


Itinerary: Chicago has so much to offer that it can be hard to decide what to see and do. You can tailor your itinerary based on your interests, your time, and your season. Some of the must-see attractions in Chicago are the Willis Tower, the Navy Pier, the Millennium Park, the Art Institute of Chicago, the Field Museum, and the Shedd Aquarium. Additionally, at Navy Pier, an immersive experience, Flyover Chicago, is bringing in rave reviews and is a great way to see the city from above. Additionally, if you plan to see major Chicago attractions, buy a CityPASS to take advantage of some big savings.

You can also explore the different neighborhoods, such as Chinatown, Little Italy, Greektown, or Pilsen, to experience the city’s diversity and culture. You can also enjoy some of the events and festivals that take place throughout the year, such as the Chicago Blues Festival, the Taste of Chicago, the Chicago Marathon, or the Chicago Christmas Market.



Things to See and Do in Chicago

View of Chicago from Navy Pier. Image Credit: Karyn Locke
View of Chicago from Navy Pier. Image Credit: Karyn Locke



Once you have planned your trip, you can start enjoying the city and its attractions. Here are some of the best things to see and do in Chicago.



Willis Tower

The Willis Tower, formerly known as the Sears Tower, is the tallest building in the city and the second-tallest in the country. You can take an elevator to the 103rd floor and step onto the Skydeck, a glass balcony that offers a stunning view of the city and the lake. You can also visit the Skydeck Museum, which showcases the history and architecture of the tower and the city.


Navy Pier

The Navy Pier is a popular waterfront destination that features a variety of attractions, such as a Ferris wheel, a carousel, a mini-golf course, a children’s museum, a theater, a cinema, and a beer garden. You can also take a boat tour or a cruise from the pier and enjoy the scenery and the city’s skyline.


Millennium Park

Millennium Park is a public park covering 24.5 acres that hosts some of the city’s most iconic landmarks and artworks, such as the Cloud Gate, also known as the Bean, a giant reflective sculpture that mirrors the cityscape; the Crown Fountain, a pair of interactive video screens that display the faces of Chicagoans and spout water; and the Jay Pritzker Pavilion, an outdoor amphitheater that hosts concerts and performances.

You can also visit the Lurie Garden, a botanical garden that showcases the native plants and flowers of the region, or the McCormick Tribune Ice Rink, a seasonal ice skating rink that operates from November to March.


Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the country and one of the most visited in the world. It houses a collection of over 300,000 artworks from various cultures and regions, ranging from ancient to contemporary.

Some of the most famous artworks in the museum are Grant Wood’s American Gothic, Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, and Vincent van Gogh’s Self-Portrait. You can also explore the Modern Wing, which showcases the works of modern and contemporary artists, such as Pablo Picasso, Andy Warhol, Jackson Pollock, and Frida Kahlo.

Field Museum

The Field Museum is a natural history museum that features over 40 million specimens and artifacts, covering topics such as anthropology, biology, geology, and paleontology. You can see some of the highlights of the museum, such as Sue, the largest and most complete Tyrannosaurus rex skeleton ever found; the Grainger Hall of Gems, which displays over 600 gems and jewels; the Ancient Egypt exhibit, which showcases over 23,000 objects from the ancient civilization; and the Evolving Planet exhibit, which traces the history of life on Earth from 4 billion years ago to the present.


Shedd Aquarium

The Shedd Aquarium is one of the largest and most diverse aquariums in the world, housing over 32,000 animals from over 1,500 species. You can see some of the amazing creatures that live in the aquarium, such as beluga whales, dolphins, penguins, sea otters, sea lions, sharks, stingrays, and turtles. You can also watch some of the shows and presentations that demonstrate the behaviors and skills of the animals or participate in some of the interactive programs and experiences that allow you to get closer to the animals, such as feeding, touching, or diving with them.



What to Expect



Chicago has something for everyone, but it also has some challenges and surprises that you need to be aware of. Here are some of the things you can expect from the city.

traveling to Chicago - Manny's Deli
Big plates at Manny’s Deli – a must for traveling to Chicago. Image Credit: Karyn Locke



Weather

Chicago is known for its unpredictable and extreme weather, especially in the winter. The city can experience snowstorms, blizzards, freezing temperatures, and strong winds, which can affect your travel plans and activities. You need to be prepared for the cold and dress appropriately, as well as check the weather forecast and the road conditions before you go out. On the other hand, the city can also have some beautiful sunny days, especially in the spring and summer, when you can enjoy the outdoor attractions and events.


Culture

Chicago is a city that celebrates its diversity and culture, and you can experience it through its food, music, art, and festivals. You can taste some of the local specialties, such as the deep-dish pizza, the Chicago-style hot dog, the Italian beef sandwich, and the popcorn mix. You can also listen to some of the genres that originated or flourished in the city, such as blues, jazz, gospel, soul, and house.

You can also admire some of the artworks and murals that adorn the buildings and streets of the city or visit some of the museums and galleries that showcase local and international talent. You can also join some of the festivals and celebrations that take place throughout the year, such as the St. Patrick’s Day Parade, the Chicago Pride Parade, the Lollapalooza Music Festival, or the Chicago International Film Festival.


Safety

Chicago is a safe city for the most part, but it also has some areas and issues that you need to be careful of. The city has a high crime rate, especially in some of the south and west neighborhoods, where gang violence and shootings are common. You need to avoid these areas and stay in the well-lit and populated areas, especially at night. You also need to be aware of your surroundings and your belongings and avoid any suspicious or aggressive people. You can also use the emergency number 911 if you need any help or assistance.



Traveling to Chicago: In a Nutshell



Chicago is a city that offers a lot of attractions and experiences for visitors of all ages and interests. You can plan your trip to Chicago by considering your budget, your transportation, your accommodation, and your itinerary. You can also see and do some of the best things in Chicago, such as visiting the Willis Tower, the Navy Pier, the Millennium Park, the Art Institute of Chicago, the Field Museum, and the Shedd Aquarium.

Filed Under: On the Go, Travel Tagged With: traveling to chicago

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