The Windy City is a vibrant, buzzing city that offers its travelers and locals endless attractions that make you fall in love with it. If you’re traveling here for the first time, it might seem overwhelming with all the must-see landmarks and must-eat restaurants on your bucket list. Our team at American Auto Insurance wants to help you plan your first trip to America’s third-largest city. So we compiled a list of some tips for what you need to know before visiting Chicago.

Ditch the Car, Find Alternatives

A wide shot of the ferris wheel and children's museum at Navy Pier in Chicago, IL

Image by rigel is licensed with Unsplash License

One thing about big cities is that there’s always going to be traffic, no matter the time of day. When trying to get around the city, ditch your car and choose to walk, take public transportation, or use a ride-hailing app. Walking might be the quickest way to get around the city without losing much of your sightseeing because you can look at the city along the way.

To avoid traffic and parking problems, take public transportation or Uber or Lyft if the weather is too cold or the place is too far to walk. You’ll reach your destination faster and spend less time in traffic and finding parking. Not to mention the cost to park in some garages or lots can be expensive. If you’re planning to use public transportation frequently during your visit, consider getting a Ventra card. This card can save you time and money while getting around the Windy City.

Prepare for the Unpredictable Weather

Before you leave your hotel or go into the city, check the weather and then check again. Chicago is on Lake Michigan, which means there’s a lake effect. While the lake provides beautiful views and fun activities during the summer, it can also affect the weather. If you’re visiting during the colder months, bring a warm jacket, winter hat, gloves, scarves, and boots because of the wind chill and the possibility of lake-effect snow.

Throughout the year, there are wind chill possibilities. Even if it’s a warm spring day outside of the city, it might feel a few degrees colder inside the metropolis. Always bring an extra jacket with you, and maybe an umbrella.

Book Activities and Tickets in Advance

If you have a few months before your trip to the city, be sure to book your activities and tickets in advance. This can help ensure you do and see the shows you’re excited about, such as theater performances or museum tours. It may also help decrease your stress levels rather than trying to get tickets the day of a show during your vacation. Additionally, some places in the city require you to buy your tickets online, like the Art Institute, so getting them ahead of time can make your day smoother.

Other prominent museums that you must see while you’re in the city include:

  • National Museum of Mexican Art.
  • Adler Planetarium.
  • DuSable Black History Museum and Education Center.
  • Museum of Contemporary Art.
  • Museum of Science and Industry.
  • Field Museum.
  • Oriental Institute Museum.
  • Shedd Aquarium.

Make Restaurant Reservations

Similar to booking your activities and tickets in advance, make sure you reserve spots at your must-eat-at restaurants. Making your reservations in advance can help ensure you have the opportunity to eat at some of the finest restaurants that Chicago has to offer. During dinnertime, skip the waits with your reservations. There are various reservation apps you can use to secure or spot, or the restaurant’s website has a page for reserving your table.

Explore Several Neighborhoods

During your trip, explore several neighborhoods rather than sticking to just a few of the popular ones. This way, you can get to know the city’s rich and diverse culture. It can let you see how the locals live, and you might even find some hidden gems, like fun local dive bars you wouldn’t have found without exploring the area. Some historic and iconic neighborhoods to check out in Chicago include:

  • Hyde Park.
  • Old Town.
  • Wrigleyville.
  • Printer’s Row.
  • Lincoln Park.
  • Lower West Side.
  • Chinatown.
  • Little Italy.
  • Logan Square.
  • Bucktown.
  • Wicker Park.
  • Andersonville.
  • The Loop.

Save Your Money and Check Out the Free or Cheaper Options

While Chicago has plenty to do that costs money, you don’t have to spend a fortune to have a good time here. You can still experience the city while saving money by checking out the free or cheaper options in the Windy City. Each year Chicago has free museum days where you can explore the plethora of history and art for free. Each museum has its own dates that offer free admission, so be sure to check the sites to find out when those days are happening.

Join in on the Local Sports Rivalries

There are two iconic Chicago professional baseball teams, which are the White Sox and the Cubs. If you’re coming during baseball season, you can join in on the local sports rivalries by attending a game at their respective fields—Guaranteed Rate Field for the White Sox and Wrigley Field for the Cubs. In the colder months, head to Soldier Field to catch a Bears game or the United Center for a Blackhawks or Bulls game. This town has no shortage of sporting events to enjoy. Grab some tickets, buy a T-shirt, and root alongside the diehard locals.

See the Tourist Attractions

Of course, when you’re in Chicago, you want to hit up all the tourist attractions that make Chicago a vibrant city. That’s half the fun of exploring a new place. Consider dedicating a day to visiting all the tourist attractions and iconic city sights. Add some of these popular activities to your itinerary:

  • The Bean.
  • Navy Pier.
  • Millennium Park.
  • Lincoln Park Zoo.
  • Skydeck Chicago at Willis Tower.
  • Buckingham Fountain.
  • The Chicago Theatre.
  • Magnificent Mile.
  • Lakefront Trail.
  • Grant Park.
  • Tribune Tower.

So there you have it, our team’s top tips for what you need to know before visiting Chicago for the first time. What do you think of our list? Do you have any other questions about something we didn’t cover? Contact us, and ask us about it. Here at American Auto Insurance, we value our clients, and we want to make sure you’re well-equipped for your travels into our iconic city.

At American Auto Insurance, we believe that getting affordable insurance quickly shouldn’t be so difficult, and we want to help you get great insurance prices. If you need help with your car insurance or you’re looking for a free insurance quote, call us at 800-483-4868.


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