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5 Tips for Visiting Chicago for the First Time

5 Tips for Visiting Chicago for the First Time

Last Updated on July 27, 2023

Visiting Chicago for the first time? Brace yourself for an experience bursting with architectural marvels, culinary diversity, and a rich cultural scene. This guide is designed to help you make the most of your maiden trip to “the Windy City”.

Read on as we uncover some essential tips to make your first visit to Chicago an experience to remember.

Why You Should Visit Chicago

Chicago, affectionately known as “the Windy City”, is a remarkable destination for tourists. It’s not just the incredible architecture that leaves visitors in awe. You’ll be just as enchanted by the rich cultural history, world-class dining, and vibrant arts scene.willis tower skydeck chicago views

Museums of international reputation are a major draw, but the city’s lively music festivals often steal the show. Outstanding parks await exploration too. There are so many things to love about Chicago, almost too many to mention.

Here are some tips for your first visit to Chicago that will help you get the most out of your visit.

5 Handy Tips When Visiting Chicago for the First Time

1. Plan Your Transfer from the Airport to Your Hotel Ahead of Time

Navigating a new city can prove challenging, particularly when you’re fresh off a flight and carrying heavy luggage. To alleviate any potential stress, book your airport transfer ahead of time. Consider a professional Chicago car service for comfortable, hassle-free transportation straight to your hotel. The city’s main airport, O’Hare, is about 45 minutes from Downtown Chicago, also known as “The Loop”.

chicago wrigley building

2. Explore Beyond Downtown, aka The Loop

Downtown Chicago is commonly called “The Loop” because the Chicago subway (known as the L because it runs on elevated train tracks above the city streets) loops around what’s considered to be the center of the city, bordered by Lake Street on the north side, Wabash Avenue (east), Van Buren Street (south), and Wells Street forms the western border. The Loop offers many fantastic things to do, including the Willis Tower, plenty of shopping, great food, and the beautiful Chicago River Walk.

However: venturing beyond it is highly recommended. Areas like Wicker Park and Lincoln Park are filled with distinct attractions and delicious restaurants, providing visitors with a more local and authentic Chicago experience. It is also interesting to see how distinctly different each of the neighborhoods feel. If you’re an active person, I recommend renting a bicycle downtown and heading north along Lake Michigan.

chicago neighborhoods

3. Invest in a CityPASS

Chicago’s top attractions are all worth visiting, but the cost can quickly add up. A CityPASS serves as a valuable solution because it grants access to five paramount attractions at nearly half the price.

Furthermore, Skydeck Chicago – an exceptional viewpoint of the city – is included in the pass, and this is definitely a Must-Visit spot. Seeing the sprawling city and the vast lake (which seems more like an ocean than a lake!) from above will give you a whole new perspective of Chicago.

views over downtown chicago

4. Embrace the Variety of Food 

Don’t limit yourself to deep-dish pizza or hot dogs when you’re in Chicago; diversity is key here! The city takes pride in its rich culinary variety spread across different neighborhoods — Korean dishes in Albany Park or Mexican cuisine in Pilsen should be on your list too. A food tour around Chicago’s broad range of tastes can prove extremely satisfying – there are a number of guided food tours, or you can create a DIY food tour, including pizza, tacos and Polish pierogies. If you’re a fan of pizza, you should definitely hop on a pizza tour – Pizza City USA offers the best Chicago Pizza tours.

chicago deep dish giordanos pizza

5. Check out Free Events 

The city constantly hosts free events for both locals and tourists to enjoy. From concerts at Millennium Park during summer to fascinating art exhibits held in local galleries, there’s always something accessible for every visitor.

See if you’re visit aligns with the Taste Of Chicago, which is the world’s largest food festival (or plan your visit around it!), or if a food truck festival happens to take place while you’re in town – they’re culinary experiences you won’t forget anytime soon. You can find out which free events take place while you’re in town by doing a quick Google search for “free events in Chicago” or “the best free things to do in Chicago this month”.

chicago gay pride parade

Is Finding Hotel Accommodation in Chicago A Hustle?

Booking a hotel in Chicago doesn’t have to be a hustle. It’s home to a wide range of hotels with accommodation, ranging from luxurious five-star establishments to budget-friendly alternatives.

Nonetheless, it pays to book your stay well in advance. This is especially true when visiting during the peak travel season or big events. There may be a big trade fair happening during the time you’re planning to visit, Lollapalooza or the Chicago Marathon – and for events like these, hotels book up quickly.

Also, deciding on the location before booking can make a significant difference. Popular neighborhoods like The Loop or Near North Side are often favored by tourists due to their proximity to main attractions. Make sure you book a hotel in an area that makes the most sense for you.

Chicago skyline from buckingham fountain

Other Things to Know About Chicago Before Visiting

  • Public Transportation is Efficient: The city’s public transportation system, led by ‘The L’ trains and buses, is comprehensive, making it easy to navigate the city without a car.
  • Weather Can Be Unpredictable: Chicago has a reputation for having quite fluctuating weather. Packing layers and checking the forecast frequently can ensure that you pack appropriate clothing. The Chicago winters are known to be brutally cold, and the summers get very hot, but can come with unexpected downpours and intense summer storms.
  • It’s truly a Sports City: Whether you’re into baseball, basketball, or football, there’s always an exciting game to catch in this sports-loving city. Check the Chicago sports calendar to see if a game happens while you’re in town. Seeing the Cubs play in Wrigley Field is an incredible experience that not just baseball fans will appreciate.
  • The City Loves Festivals: Chicago hosts several festivals throughout the year covering music, food, art, and more. Checking the schedule before your visit could lead you to some entertaining experiences. The above-mentioned Taste Of Chicago is the most popular food festival, and Lollapalooza is one of the best music festivals in the country.

wrigley field chicago

As you set off on your maiden voyage to explore Chicago, remember that the city offers a dynamic fusion of attractions and experiences. With these tips in hand, you can embrace the city’s charm and make your adventure truly memorable.