Nomad in Contemporary Chicago: The Complete Guidebook

There is an unstoppable movement of people who have done the leap of faith and escaped the matrix. I’m talking about these extraordinary individuals who could not live one more day in their 9-5 comfort zone.

Their desk job started to drain the life out of their bodies and the office hours were just an empty period of time. So, they did the impossible.

They found a way of working remotely at their own pace, at their own time. And not only that, they could work from every place on earth they desired.

Thus, traveling and seeing the world has become part of their lifestyle. Working, now, has a different meaning and feels more fulfilling thanks to the different, each time, working environment.

The world is at your feet and you can choose where to live this month. You are a traveler!

In this article, we are going to talk about the most interesting activities that a digital nomad can do while visiting Chicago.

There are many ways of traveling to this big Illinois city on Lake Michigan. If you find yourself flying there, the best way is to book an airport taxi to Chicago O’Hare airport.

This is the most convenient, reliable, and affordable way to enter the city with an AtoB airport transfer. You are going to have a head start as your airport transfer driver will bombard you with suggestions about the coolest places to visit.

So, without further ado, let’s explore Chicago!

Fall in Chicago

Chicago overview

Don’t worry, we aren’t suggesting you hurt yourself! We are talking about this majestic season of the year which is full of romance and cozy feelings.

You want to dress warm and spend time in the deep-orange and yellow from the fallen leaves in parks walking. Chicago is known for two events!

Jack’s Pumpkin Pop-up

If you’re in Chicago from late September to early November, be sure to make time for this unique event. This is a pumpkin patch pop-up right in the middle of the city!

Being an event there are many cool activities for you to do there like ax throwing! You can participate at carnival games, get lost in a corn maze and indulge in the many food trucks that have to offer!

So, if you’ve just arrived in Chicago, ask for your AtoB airport taxi to drive you there!


Yes, the famous German festival is held in Chicago too! There are many venues that host this festival throughout Chicago. The biggest one is at Lakeview’s St. Alphonsus church that takes place in late September, every year.

Chicago Oktoberfest

Finally you have a reason to celebrate drinking beer and stuffing your mouth with pretzels. Prost!

Chicago River

Chicago does have a river. It’s a unique feeling walking by the city’s river just as the sun sets. The city is transforming to this relaxing orange entity while there is a feeling of melancholy floating in the atmosphere.

Chicago is no exception. In fact, it can offer more than these lazy afternoons. You can glide along its river with a kayak!

With just a few quick lessons, you are entitled with a glorious and unique self-guided tour in your own kayak. For a few hours or for the entire day, the Chicago River is yours to explore.

Just like the rest of the city if you have a chauffeur from AtoB’s airport transfer services



American football not European. Chicago is home of the Chicago Bear at Soldier Field. There aren’t many home games each year, therefore, you must grab the opportunity of watching the Bears playing home.

Chicago Sports


Two words. Chicago Bulls. Since you’re in Chicago you have to pay a visit and watch a basketball match of the most famous team of your childhood.

You must visit the United Center where Michael “Air” Jordan became who he is and joined the pantheon of All Starts. For many, the Chicago Bulls is Chicago.


Like any big city, there are many zoos for the animal lovers to visit. In Chicago we suggest the Lincoln Park Zoo. You’ll have a FREE(!) access to 35-acre land where more than 1,000 animals are calling home.

Lincoln Park Zoo

There are lions, bears, penguins, eagles, snakes, crocodiles, turtles and the list goes on and on. You can also book an airport taxi and check the monkeys at the Regenstein Macaque Forest.

Museum of Ice cream

Do you remember the Charlie and the Chocolate Factory movie? This is its closest adaptation in real life.

You will have access to numerous experiential rooms that will try to fulfill the needs of your inner child. There is an ice-cream science lab, a mini-golf course, and…a sprinkle pool!

You will learn about the history of local ice cream ventures in the most fun way! Don’t try to bite anything though, the majority of them are not edible! Just wait to go out into the real world and have some real ice cream.


So, when you stay in Chicago and finish with your online job, reserve an airport transfer and organize the rest of your day in a way to fit as many activities as possible.

Sharing is caring!

Leave a Comment