Tips in Traveling to Chicago for the First Time

Tips in Traveling to Chicago for the First Time

If you’re traveling to Chicago for the first time, you might be wondering what you need to know before you get started. You will want to know more about Downtown Chicago, the Skydeck, and Millenium Park. In this article, we’ll provide a quick overview of all the top Chicago sights. Then, you can make your way to those spots. And if you have time to spare, visit the museums and Old Town.

Downtown Chicago

Whether you’re visiting the city for the first time or are returning for a second visit, you’ll want to plan your trip from a local’s perspective. The following tips will help you make the most of your time in Windy City. First, plan to stay at least two days in Chicago. Even though the city has plenty to offer, you should avoid trying to cram everything into a single day. Instead, focus on seeing the main attractions and saving time for other activities, such as food and shopping.

Next, make sure to take advantage of free admission days and check out Chicago’s many museums. One of my favorites is the Art Institute, located downtown near Millennium Park. The Art Institute is free on Thursdays from 5 to 8 PM. It is also located across from the start of Historic Route 66, making it a great place to visit. Don’t miss the Shedd Aquarium, Adler Planetarium, Field Museum of Natural History, and Museum of Science and Industry.

Old Town

If you’re going to Chicago for the first time, you may be curious about the old-world charm of Old Town. This neighborhood is a short train ride north of downtown and features Victorian-era buildings and a lively dining scene. Visitors can enjoy the eclectic mix of restaurants and small shops, as well as the theater which runs seven nights a week. You can also check out the 3 Arts Club CafĂ© inside the iconic Restoration Hardware store.

The Old Town is also home to four neighborhood theaters, including the renowned Second City Theater. Visitors can catch a sketch and improv comedy at The Second City or watch a stand-up comedy at Zanies Comedy Club. There are also contemporary dramas at A Red Orchid Theatre and an improvised Japanese game show at BATSU! While this area is famous for its nightlife, it’s not for the faint of heart.


If you’re planning to visit the Skydeck when traveling to Chicago for the first time, you’ll want to make sure you plan your visit before the sun sets. The best time to visit the observation deck is between 30 and 45 minutes before sunset, so be sure to arrive at least 30 minutes before. You can also check out the Chicago sunset calendar on before heading to the Skydeck.

The 360 CHICAGO observatory is located on the 96th floor of the iconic John Hancock building. From there, you’ll enjoy 360-degree views of the city. Although not as high as the Skydeck, this observation deck is still a fantastic way to take in the city and its architectural features. There are many vantage points from which to look, and you can even enjoy a meal or drink while watching the city lights from the observation deck.

Millenium Park

Whether you’re visiting Chicago for the first time or returning for a visit, you won’t want to miss Millennium Park, an urban oasis in the heart of the city. You can park in the park for as little as $6 an hour (using a discount parking app such as SpotHero) and walk to Millennium Park in less than an hour. Millennium Park is also home to the BP Pedestrian Bridge, the first bridge in the world designed by Frank Gehry. And don’t forget to take a look at the McDonald’s Cycle Center, which was sponsored by the fast-food giant after the park opened.

Millennium Park is located downtown, so you’ll find it easy to access via the CTA bus system. Alternatively, you can take a walk along the Chicago River, DuSable Bridge, or Michigan Avenue. You can also take the Lakefront Trail, which connects Millennium Park with Maggie Daley Park. If you have time, you can enjoy the park in the evening. The Chicago River just steps away from Millennium Park.

Free museums

If you’re a newbie to the city, you can take advantage of free museum days. You can also buy a membership to enjoy discounts at all times. Some museums have reciprocal agreements, such as the Nationwide Museum Passport Program. We’ll focus on general admission, but there are also discounts for military, first responders, and teachers. You can also take advantage of the Museums for All program, which offers free admission for up to six people.

Free museums in Chicago are plentiful. Visitors can enjoy the Art Institute and the Field Museum for free on certain days. Depending on the museum, you might also be able to take in the free exhibits at the University of Chicago’s Museum of Science and Industry. While most museums require a fee to enter, free admission to the University of Chicago Art Museum is available year-round. During the summer, the Lincoln Park Zoo is open to everyone.

Places to stay

Whether a first-time visitor or an experienced traveler, you’ll find an incredible number of places to stay in Chicago. The city is spread across 77 different neighborhoods, each with its own unique charm and points of interest. These neighborhoods are the perfect place to stay if you are interested in a cultural immersion or are looking for the perfect staycation. Below are just a few suggestions:

The Loop – This area is the center of the city and offers easy access to the city’s best attractions and restaurants. Aside from being convenient to public transportation, The Loop is also one of the safest areas in the city. Depending on your taste, you may want to consider staying in River North, Lincoln Park, or the Gold Coast. The West Loop has some of the city’s best restaurants and nightlife.