Travel Tips for Chicago: 9 Useful Things To Know Before Visiting Chicago

These travel tips for Chicago will serve you well, whether you’re planning a trip to Chicago for the first or the twenty-first time. Make the most of your visit to Chicago by learning all that this amazing city on the southeastern tip of Lake Michigan offers. Start with these 9 useful tips you should know before you visit, below. 

CONTENTS – In this article, you’ll learn the best travel tips for Chicago, including:

Tips For A Stay In Chicago

Chicago is an important and iconic city, which is why it deserves to be visited, at least once. There are so many things worth checking out. 

However, if you’re a first-time visitor—or even if you’ve been to Chicago more than a few times—it might be challenging to know what to do and what to expect. 

So for that reason, here are some tips and suggestions that will help you have an amazing Chicago adventure. 

1. Know What You Want Out of Your Stay

Before we go any further, it’s important to know what you want out of your stay. It will set your expectations for the trip. For instance, 

Are you more into visiting museums and exhibitions? 

Maybe you prefer to go bar hopping or clubbing? 

Or maybe you just want a laid-back experience without any strict expectations? 

Whatever the case, knowing this upfront will help you decide which places you want to visit in Chicago, and what activities to pursue. That way, when the trip ends, you won’t feel disappointed.

2. Make Sure to Find the Best Accommodation in Chicago

Sure, Chicago is abundant with both budget and luxurious hotels, so if such accommodation types fit your needs, then feel free to enjoy it. You’ll find plenty of 5-star hotels in Chicago, including The Waldorf Astoria, The Ritz Carlton, The Longham, as well as boutique hotels and others.

In addition to hotels, you might also look into Airbnb accommodations. They are a good option if you want a more private setting, like renting out a private home in the Chicago suburbs. Or, you can see what it feels like to live in a chic apartment in the heart of the city. 

Before you decide to make a reservation with an Airbnb property, it’s important to compare the price you’re paying to the overall prices in that area of the city. 

3. Whenever You’re in Doubt, Just Go Downtown

In Chicago, the downtown, also known as The Loop, is the most famous part of the city. It’s also considered the best area to stay in when in Chicago. 

That’s where you’ll find the business district, and all the well-known Chicago skyscrapers are there. Plus, historical, architectural landmarks are also located there, as well as theaters and music venues. 

You may not know this, but Chicago is one of the most photographed cities in the word

Related Article: Add these must-see attractions in Chicago to your itinerary.

4. If You’re a Party Animal, You Should Visit River North

River North is an area of Chicago known for:

  • Upscale galleries
  • Boutique shops
  • Museums

However, the biggest gem is the amazing and electrifying nightlife.  If you consider yourself to be something of a party animal, then this is the Chicago area you should absolutely visit. 

You’ll find many clubs and bars to choose from. Feel free to try all the ones that seem new and appealing. 

But if it’s your first time visiting, then River North is a must-see place. 

5. Feel Free to Explore and Roam 

Is it safe to visit Chicago as a tourist? Depending on whom you ask, you’ll get different answers regarding Chicago safety and crime levels. 

Of course, as a tourist, it’s your job to take care of your own wellbeing, and if you’re cautious, you’ll be fine. 

However, certain Chicago areas, such as South Side, have been riddled with crime—but recently, efforts to beautify the place make it more appealing to everyone. 

Therefore, if you want to explore and roam such places, feel free to do so. Just make sure to check about all the safety measures, especially in times of the global pandemic.

6. Try the Amazing Chicago Food

Chicago is known for amazing food, especially the famous Chicago-style pizza. This pizza is also known as deep-dish pizza. Some consider it the best in the world!

And after eating pizza, it’s time to get some dessert, for example, ice cream. The great news is, Chicago has wonderful ice cream spots that also sell sundaes, milkshakes, and smoothies, to name only some choices. You’ll also find small-batch Gelato and vegan options. 

But, if you end up getting food stains on your clothing from this Chicago food frenzy, don’t worry. You can always get help by looking up the best green cleaning in Chicago. They will clean your clothes and make them look as good as new! 

Therefore, don’t be shy to indulge in all the delicious foods and meals that Chicago has to offer. You’ll definitely feel full and satisfied when you’re eating in Chicago.

Trivia Fact: Caramel Corn, a popcorn mixed with sweet caramel candy coating, made it’s debut to the world at Chicago’s World’s Fair in 1893.

7. Enjoy the Sports Culture 

People in Chicago love their sports! So, if you want to feel like a true local, then you’ll want to embrace and enjoy the sports culture of the city. 

In general, Chicagoans love sports as their main small talk topic, so if you’re looking to start a conversation with any local, then sports will likely do the job. 

But, also remember that the locals are fiercely loyal to their sports teams, so don’t try to downplay them or badmouth their teams. After all, you are a guest in their city, so don’t forget your manners! 

8. Feel Free to Cycle – and More! 

Exploring Chicago can be a bit time-consuming, even if you take the L and other forms of public transport. But, since there are so many neighborhoods, chances are you’ll have to rely on trains and buses. 

However, if you’re looking to avoid the traffic, then feel free to consider cycling. There’s also a Chicago-based bike share system, and a lot of lanes and trails.  The most notable trail is the Lakefront Trail, which is very much favored by local cyclists. 

Chicago is a great city for outdoor enthusiasts, whether that means cycling along the shore, taking a hike on the 606, sailing on Lake Michigan or kayaking the Chicago river.

Related: Find out all about riding ebikes if you’re thinking of going that route.

9. Try Visiting at the Right Time

Visiting Chicago during school breaks and bank holidays isn’t the smartest idea, especially if you’re planning to check out a lot of places in a short period of time. This is because Chicago is a popular city break destination. 

You’ll want to avoiding such peak periods to ensure you have a better and more productive visit. 

Summer season is always a safe bet, despite the heat. You can see numerous summer festivals, plus all the rooftop bars and outdoor dining establishments are open, which is a great bonus. 

If the weather concerns you, then it’s best to visit in April-May or mid-September-October. These are the periods when the weather is pleasant enough, and it’s less busy compared to summer. 

Final Thoughts on Tips for Chicago

Chicago is a beautiful city, with stunning architecture and a skyline that definitely deserves your attention. So visiting Chicago is a great way to meet a different side of America that isn’t all about New York and LA. 

Just remember to book everything in advance to be sure that you’ll be able to see everything. Even if you have one free day to spare, going to Chicago is a great opportunity to gain valuable new experience and get a taste of one of the busiest and most eclectic American cities. 


Photo credit: Feature – Chris Dickens (Unsplash), Waldorf Astoria Chicago Exterior – Waldorf Astoria Chicago (© 2021 Hilton), all others courtesy of Canva Pro.

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Jackie Gately

Jackie Gately is a seasoned travel writer, photographer, and marketing consultant who is passionate about travel. She loves casual-luxury experiences, coastal getaways, cultural attractions, and local, wholesome food and wine pairings. A perfect day ends with her toes in the sand or by chasing the sunset with her camera--ideally both.

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