Traveling to Chicago for the First Time: 7 Tips & Tricks 2023

Traveling to Chicago is one of the best destinations you can visit in a lifetime. Aptly named the City in a Garden, Chicago is a beautiful blend of Midwestern charm and a fast-paced big city.

There’s plenty to see and do, and you’ll need more than one visit to feel the City and all it has to offer.

In the article below, we picked the best local pieces of advice for first-time tourists coming to Chicago. You’ll have a greater perspective on organizing your time and money to make the most of the trip. So let’s get to it!

Best Tips for First-Time Tourists in Chicago

Before we jump into the main attractions you can find in Chicago, let’s revise your documents for a minute.

Please remember that any visitor Traveling to Chicago US without a green card must have a visa and a valid passport.

If your passport is expired, don’t panic, you can still go on your trip, but you must act fast. Therefore, you can take a US passport photo online and have a stress-free trip there.

Now back to Chicago: here are the best tips you can take from locals here in the City.

1- Don’t Rent A Car

Don't Rent a Car

If there’s anything Chicago is known for, it’s the outstanding means of transportation. If you need to travel across the City, or move from one area to another, then renting a car isn’t the wisest choice.

Yes, it may be cleaner than public transportation, but you’ll spend the entire day stuck in traffic instead of exploring the City. Plus, it’s not even economical as cars spend most fuel while being stuck in traffic.

Therefore, use public transportation because it’s super affordable and practical. A train fare is about $2.50, and the bus fare is around the same amount, with many bus and train stops at frequent destinations.

2- Don’t Put Ketchup on Your Hot Dog


A love letter to a foodie says if you want to enjoy a hot dog from Chicago, always follow this order:

  • Mustard (on the dog)
  • Relish
  • Onion
  • Tomato
  • Pickle
  • Peppers
  • Celery Salt

First, you put the tomatoes between the hot dog and the top of the bun while the pickles come on the bottom.

Put the onions on the sides of the bun and the mustard on the dog – It’s a rule. More importantly, forget about ketchup. If you don’t want to ruin your trip, don’t even mention ketchup in Chicago.

3- Book Everything in Advance

Book Everything in Advance

This is imperative for big cities like Chicago, especially if you visit the metropolis during a hot touristic season.

Remember that people book everything in advance, and often, even if there are many hotels down the streets, it’s a hopeless attempt to find a stay for 5-6 days in a row in the same place.

Hotels can host you for a day or two, but you must relocate to another. Therefore, make sure to book your stay in advance.

Also, it’s good to know to read the cancellation policy if you’re booking a hotel. Most hotels retain the deposit sum if you cancel before the arranged time.

The same goes for trips to museums. Many book their tickets online, so they have a secure trip to the museum.

Lastly, if you’re looking for a safe location in Chicago, then we strongly advise you to find a stay downtown. Chicagoans call this area “The Loop,” and you can discover it to fit every budget – high or low.

4- Make Rational Plans

Make Rational Plans

Many tourists coming to Chicago for the first time make the same mistake – they book too many places they cannot visit in 2-3 days.

Navigation is critical when arriving in Chicago for the first time, especially in such a short period.

Open Maps, see where your hotel’s, and see what nearby attractions you can visit. Or, if you want to visit particular places, look for apartments, hotels, or hostels near the area.

You must have at least one type of plan — either book near the museums or parks or visit the attractions near your accommodation.

5- Try an Old Fashioned

Try an Old Fashioned

If there’s something you mustn’t leave Chicago without, then that’s the Old-Fashioned cocktail on the rooftops.

If you surf a bit online, you’ll realize that Chicago takes all credit for the cocktail. Many people leave reviews that Chicago rooftops have the best cocktails to offer.

Therefore, jot it as you read — Try Old Fashioned Cocktail on Rooftop.

6- Enjoy Chicago for Free


Besides all those museums of art and science, one of the best things you can do in Chicago enjoys the free offers.

Go for a walk in Millenium Park. You can learn more about Chicagoans’ past times and their daily lifestyle.

Then, visit Lincoln Park Conservatory or Lincoln Park Zoo. Also, keep in mind that some museums offer free days.

You can check online for more information and visit one of Chicago’s most acceptable for free.

7- Use the City Passes

Due to the large influx of tourist interest in Chicago, the city offers City Passes to simplify the process of tickets and crowd the museums.

These City Passes, as the name suggests, allow you to visit 2-5 of the most popular attractions of your choice. However, these passes have expiring dates, some last two months, while others previous nine months.

Depending on your stay and how many museums you want to visit, you can get a pass to fit your needs.

Reviews from actual user’s online claim that City Passes are time savers and worth it. You can google it yourself for more information and experiences.

Final Say

There’s so much more to talk about when you are Traveling to Chicago for first time, but in a nutshell, you must know where you’re going and have a good plan when you arrive here.

Make a plan of all the places you want to visit, all the food you want to try, and get packed.

And if you don’t get to see everything you wanted, don’t despair – you’ll have to plan Traveling to Chicago soon, and you can never travel enough! Bon Voyage!

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