How to Make the Most of Your Trip to Chicago

Chicago is one of the biggest cities in the United States, so it’s no surprise that it’s such a hot destination for tourists and business travelers alike. But if you want to make the most of your trip to Chicago, you should think proactively about how you want to plan your trip.

These are some of the best steps to take to do it.

Plan (and Book) in Advance

First, make sure you plan and book your trip in advance. Chicago is one of the most populated and exciting cities in the United States, so it’s a hub for both recreational travelers and businesspeople. If you wait too long to book your reservations, you may have trouble finding appropriate accommodations for your needs.

Plus, if you have more time to plan your trip and think about what you want to do, you’ll be able to do more research and discover more attractions.

Travel in the Off Season

If possible, try to travel during the off-season. The summer, bank holidays, and school vacations are all prime times for families and individuals looking to enjoy Chicago. You’re much better off traveling in the winter or during times when most people are working. This way, you can save money, deal with fewer crowds, and have more attractions all to yourself.

Use a Car Service

A car service in Chicago can simplify the process of getting to and from the airport. You’ll have a professional driver who can get you to your hotel (or another destination of your choice), and you won’t have to worry about local traffic, navigation, or personal safety. As an added bonus, car services look prestigious and professional, so you can end up making a better impression with the people you’re about to meet.

Stay in the Heart of Downtown

Consider staying in the heart of downtown. Chicago is a dense and very walkable city, so if you have accommodations in the middle of the city, you can reach almost anything in a reasonable amount of time. If you don’t feel like walking, there are plenty of other transportation options available to you, such as:

·   CTA buses. CTA buses in Chicago are highly reliable and can get you almost anywhere.

·   The L. The “Chicago L” refers to the elevated train system that runs throughout Chicago. This system is easy to navigate and surprisingly fast.

·   Bike sharing. If you’d prefer to travel on your own, consider using a bike sharing service.

Visit the Free Attractions

If you’re traveling on a budget, or if you just don’t feel like spending money unnecessarily on your trip, focus on the many free attractions available in Chicago, such as:

·       Millennium Park (and other parks, trails, and beaches). Millennium Park is an enormous and scenic park where Chicagoans gather regularly. If you’re lucky, you might even get to enjoy a free concert. Grant Park and Maggie Daley Park are fun places too.

·       Navy Pier. If you like amusement park rides and lakefront scenery, head to Navy Pier. Be sure to check out their special events – and meet some new people.

·       The Lincoln Park Zoo. If you’re an animal lover, you’ll be pleased to learn that the Lincoln Park Zoo in Chicago is entirely free as well.

Head to Local Neighborhoods

We often think of “Chicago” as one big city. But the truth is, there are many independent neighborhoods and areas with different cultures, aesthetics, attractions, and vibes. Chinatown, Greek Town, and Little Italy, for example, can all provide you a glimpse into a different area of the world – and an entirely different culture.

Go to the Museums

Museum Campus in Chicago is home to multiple interesting locations: the Field Museum, the Shedd Aquarium, and the Adler Planetarium. At the Field Museum, you can discover countless artifacts from our natural and archaeological history. At Shedd Aquarium, you can see thousands of live marine species on display. And at Adler Planetarium, you can look at the stars and learn more about our place in the universe.

Don’t Bother Trying to See Everything

Finally, don’t bother trying to see everything in Chicago in one trip. There are simply too many sites to see. You’re better off focusing on your top priorities and allowing yourself plenty of time to truly enjoy them. You can always come back in the future!

You may not be able to see everything in Chicago in one visit, but you can see more, do more, and have more fun if you prioritize the strategies in this guide. Once you get home, you can take note of what you didn’t see or do – and prioritize those items for your next trip.

Remember, never travel without travel insurance! And never overpay for travel insurance!

I use HeyMondo. You get INSTANT quotes. Super cheap, they actually pay out, AND they cover almost everywhere, where most insurance companies don't (even places like Central African Republic etc!). You can sign-up here. PS You even get 5% off if you use MY LINK! You can even sign up if you're already overseas and traveling, pretty cool.

Also, if you want to start a blog...I CAN HELP YOU!

Also, if you want to start a blog, and start to change your life, I'd love to help you! Email me on In the meantime, check out my super easy blog post on how to start a travel blog in under 30 minutes, here! And if you just want to get cracking, use BlueHost at a discount, through me.

Also, (if you're like me, and awful with tech-stuff) email me and my team can get a blog up and running for you, designed and everything, for $699 - email to get started.

Do you work remotely? Are you a digital nomad/blogger etc? You need to be insured too.

I use SafetyWing for my digital nomad insurance. It covers me while I live overseas. It's just $10 a week, and it's amazing! No upfront fees, you just pay week by week, and you can sign up just for a week if you want, then switch it off and on whenever. You can read my review here, and you can sign-up here!


So if you’re ready to…..

1) Change your life
2) Travel the world
3) Get paid to travel
4) Create a positive influence on others
5) Be free of offices and ‘real world’ rubbish

Then Sign Up Below and Let’s Get Started!

Follow me on Instagram @onestep4ward