Chicago: A Business Traveller's Guide

your complete introduction to USA's Windy City

Travelling to Chicago?

Are you planning on travelling to Chicago for work? Get to know the US city better in this comprehensive guide for business travellers.

Colloquially named “The Second City” for its historic rivalry with New York City, Chicago is more than a match for its world-famous counterpart. A booming business scene, underpinned by The Loop business district (the second-largest of its kind in North America), is a testament to the city’s economic clout, while picture-postcard views across the Chicago River give a glimpse into the softer side of Illinois.

Chicago is the perfect place to test the balance between work and play. Beyond the boardrooms and tech haven along the River North, you’ll find the iconic Navy Pier with its Ferris wheel crown, the architectural delights of Millenium Park commanded by the ultra-polished Cloud Gate sculpture, and the 110-year-old Wrigley Field home of the Chicago Cubs Major League Baseball team. 

Come the evening, you’ll be spoilt for choice amid the bustle of traditional jazz clubs and stunning rooftop bars offering sweeping views across the patchwork of buildings old and new. Those craving a bigger slice of Chicago’s culture can tuck into a delicious deep-dish pizza – a style developed in the city in the early 1940s. 

In this comprehensive guide to Chicago for business travellers, we delve deeper into navigating the city’s unique corporate landscape, offer our top tips for getting around, and pick out our top 3 things to see or do to make your trip unforgettable. 

Chicago Fact File

The seal of Chicago

The Seal of Chicago featuring the 1837 date of the city’s inauguration, a sheaf of wheat standing for the fertility of the Illinois prairies, a depiction of Lake Michigan, and the Indians, the original settlers of the Chicago region.


The official language is English. 


US Dollar ($)

Avg. Temperatures

Spring (Mar-May) = 12°C (54°F)
Summer (Jun-Aug) = 22°C (71°F)
Autumn (Sep-Nov) = 11.5°C (52.7°F)
Winter (Dec-Feb) = -3°C (26°F).

Getting To Chicago

By Air

Chicago has two major airports: O’Hare International Airport (ORD) on the northwest side of the city, approximately 17 miles (27 kilometres) from The Loop, and Midway International Airport (MDW) located 12 miles (19 kilometres) away in the southeast. Both handle flights from all over the world.

icon car

By Road

Chicago sits at the convergence of several major interstate highways, making it easily accessible. The I-90 (Kennedy Expressway), I-94 (Dan Ryan Expressway), I-55 (Stevenson Expressway), I-290 (Eisenhower Expressway), and I-294 (Tri-State Tollway) all intersect within the city limits.

By Train

Chicago Union Station acts as a central hub for Amtrak, the national passenger rail service in the United States, connecting the city to major locations throughout the Midwest and beyond. Metra, a separate commuter rail system, complements Amtrak by providing connections to Chicago’s suburbs.

Hot air balloons over Sydney Harbour

Business Culture & Etiquette


Chicago boasts a vibrant business scene defined by a direct communication style and friendly Midwestern charm.

First and foremost, Chicagoans value efficiency and getting things done. Business communication tends to be clear, concise, and to the point. Don’t be surprised by a more direct approach in meetings or negotiations – it’s seen as a sign of respect for everyone’s time.

Chicago’s business attire leans towards professional yet comfortable. Think “smart casual.” Tailored trousers, a button-down shirt, or a well-fitting dress are generally appropriate. Suits are still worn in more formal settings, but a blazer can do the trick most of the time.

Here are a few other top business tips:


    • Chicago is fiercely proud of its deep-dish pizza. If the opportunity arises, embrace the local delicacy and participate in the deep-dish vs. thin-crust debate.
    • Chicago is a die-hard sports town. Knowing a bit about the Bears, Bulls, Cubs, or Blackhawks can spark conversation and create a sense of camaraderie.

Crime & Safety


Chicago has developed an unfortunate reputation as being a city with a higher-than-average rate of violent crime, with a Gallup poll in 2023 showing that only 27% of Chicagoans considered the city safe

However, this is largely due to organised gang activity. Visitors to Chicago are unlikely to encounter any serious crime during their visit, particularly if they remain in the central metropolitan areas such as the Magnificent Mile, Millennium Park, and the Loop. Indeed, Chicago is a bustling tourist destination deemed safe by governments across the globe. 

Here are a few of our other top safety tips:


  • In Chicago, as throughout the US, the emergency number for police, fire, and ambulance services is 911.
  • Keep your valuables close, especially in crowded areas. Consider a money belt or a crossbody bag that keeps your belongings secure against pickpockets.​
A view of the coastal suburbs in Sydney

Getting Around Chicago

The Chicago “L”

The Chicago “L” is an elevated train network.  Eight train lines comprise the “L” system, each designated by a distinct colour: Brown, Red, Blue, Green, Orange, Pink, Purple, and Yellow. They run frequently, especially during peak hours, and you can typically expect a train to arrive every 5-10 minutes. Fares can be paid for individually or with a Ventra farecard.


Over 140 bus routes crisscross the city and most destinations can be reached by bus. Operated by the Chicago Transport Authority (CTA), bus trips are affordable and can be planned in real time using the CTA Ventra mobile app. Several routes also form a comprehensive night bus network that run 24/7. These can be found at stops on transport maps designated by the prefix “N”.


Divvy Bike Sharing

Divvy, Chicago’s bike-sharing system, is an affordable way to explore the city on two wheels. Hundreds of Divvy stations are spread across the city, with over 800 docking points (as of 2022). You can get a daily, 3-day, or annual membership, or simply pay for a single ride if you’re a casual user. Rates are generally affordable, with single rides costing around $3.

Top 3 Things To See Or Do In Chicago

If you find yourself with a bit of free time on your business trip, Chicago is an interesting and vibrant city with plenty to explore. Here are our top 3 recommendations…

A view of Sydney Opera house as seen across the harbour
1. Millenium Park


This sprawling 24.5-acre public park found in The Loop community district is a must-see for any visitor to Chicago. It’s home to some of the city’s most iconic landmarks, including Cloud Gate (better known as “The Bean”), Crown Fountain, and the rooftop Lurie Garden.

Millenium Park is also home to the Jay Pritzker Pavilion, a striking, sci-fi-looking venue designed by Frank Gehry which often hosts outdoor concerts, festivals, and performances. It’s difficult to miss – the stainless steel ribbons that form the pavilion’s roof creates a canopy that shimmers in the sunlight.

An Aerial view of Bondi Beach, Sydney in the daytime summer
2. Art Institute of Chicago


The Art Institute of Chicago is a world-renowned museum boasting an encyclopedic collection of over 300,000 pieces of art spanning centuries and continents.

Housed in a beautiful Beaux-Arts style building – an artistic delight in its own right – the Institute is particularly lauded for its Western European and American pieces, including masterpieces such as Georges Seurat’s A Sunday on La Grande Jatte and Pablo Picasso’s The Old Guitarist



Koala Bear in taronga zoo in Sydney
3. Navy Pier


Navy Pier is an iconic sight on the shores of the stunning Lake Michigan. Built in 1916, Navy Pier was originally designed as a shipping and recreation facility. Now it is a waterfront entertainment complex featuring an amusement park (home to the city’s famous Ferris wheel), a regular schedule of live comedy and music performances, and a wide range of restaurants and eateries.

For those looking to explore more of Lake Michigan, sightseeing cruises depart from Navy Pier, taking passengers on a journey which offers stunning views of the Chicago skyline. 

In Conclusion

Chicago thrives as a business travel destination, offering a dynamic blend of big-city energy, world-class infrastructure, and a vibrant cultural scene. Its central location in the United States makes it easily accessible from both coasts, while O’Hare International Airport opens the gates to flights worldwide.

Beyond its commercial prowess, Chicago provides a wealth of options to unwind and explore after a productive day. Delegates can delve into the city’s renowned art scene at the Art Institute, relax in Millennium Park’s scenic green spaces, or savour a traditional deep-dish pizza.

So, whether you’re a seasoned professional attending a conference or a novice business traveller seeking a new adventure, the so-called “Windy City” offers more than enough to guarantee a productive and unforgettable experience. 

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