A Business Travel Guide to Chicago

Staying in Chicago, Illinois

The USA’s third largest city, Chicago is a metropolitan oasis where bustling city life meets tranquil beaches along the coast of Lake Michigan. With its infamous Chicago Loop business district combining commercial space with high class restaurants, bars and events, Chicago is ideal for business travellers wishing to make the most of the growing ‘bleisure’ travel movement.  

With world-renowned architecture such as The Bean and the Willis Tower, and plenty of entertainment options giving it its nickname: the ‘Silicon Valley of theatre’, corporate travellers in Chicago will never be short of things to do and see in their downtime. Chicago is already an economic titan, but promising construction projects and commercial developments, such as a new skyscraper projection at Lake Shore Drive, are mirroring this city’s future growth – making it a popular destination for growing businesses and an exciting city for assignees.  

Visiting Chicago, Illinois - Key Information

Weather in Chicago

Known as the ‘Windy City’ for a reason, expect wind on your business trip to Chicago. Chicago winters are known to be colder than most other cities in America, with snowfall and sub-zero temperatures not uncommon in the months between November and April. A warm coat and lots of layers will be needed by those visiting during the winter months. On the flip side, summers in the Illinois capital are warm, reaching average highs of 27 Celsius in July, its hottest month. While Lake Michigan brings a welcomed breeze to the lakeside, the city centre remains humid, making breathable fabrics essential to the summer commute.  

Currency in Chicago

US Dollar (USD)

Currencies can be exchanged at most hotels and airports however, business travellers in Chicago should be aware that fees and exchange rates here can be pricey. Monzo and Revolut cards would be great solutions, performing currency exchanges as you pay, with no additional fees, and compatible with digital wallets for easy spending across the city.  Chicago is largely a cashless city, however, cash is still sometimes preferable, for instance when tipping waiting staff and in small convenience stores. Like the rest of the country, tipping is a common custom in Chicago, with 20% expected for meals and at least $1 per drink at most bars.  

Health & Well-being in Chicago

Chicago is home to more than 500 green spaces, including Lincoln Park, making outdoor exercise easily accessible. The lake front trail is popular among residents, stretching 18.5 miles with cycle, running and walking lanes throughout. Lake Michigan’s light waves make water sports an exciting option to both locals and visitors. Kayaking, paddle-boarding, and surfing are just some of the activities on offer at the beachfront. During the icier months, corporate travellers in Chicago may want to make the most of the city’s multitude of gyms and exercise classes. From state-of-the-art gym facilities to more intimate exercise classes, options are available for business travellers of all budgets and fitness preferences.  

Data in Chicago

For corporate travel to Chicago, network coverage, to keep connected while out and about, is vital. Mobile SIMs can be purchased both before travel and upon arrival. SIMs bought before travel offer the convenience of immediate connectivity and relieve visitors from finding a SIM card after landing in a new place. However, international roaming costs can be steep and opting to purchase a SIM on arrival will allow access to local rates. The most popular SIM operators in Chicago include Verizon, AT &T, T – Mobile, and US Cellular, with SIMs available from their many stores around the city. Alternatively, airports and convenience stores are great options for SIM purchase.  

Plug Type: Types A & B

Cuisine in Chicago

A business trip to Chicago would be incomplete without trying the authentic deep-dish pizza. A thick, buttery crust loaded with mozzarella and tomato sauce; this iconic meal can be found all over the city. Often neglected by tourists, Chicagoans are proud of their own hot dog variant, known as the Red Hot. Made from a beef frankfurter in a poppy seed bun filled with various toppings as celery salt, mustard, and dill pickle, Red Hots are available from Chicago’s many street vendors, provided the no ketchup golden rule is respected!  

Speaking the Language in Chicago, Illinois

Chicago is a melting pot for language and culture. While English is principally spoken, the many Spanish, Polish and Chinese communities make these languages common too. ‘Chicagoese’ is the niche dialect of phrases thrown around by locals in the state capital. While seemingly wacky, understanding some key phrases can ease your transition to the city. Here’s the low down of must-know expressions: 

Hunnert – One hundred. Used by locals particularly for street names because each Chicago block is equal to a hundred. When being given directions, for example, you may hear that you are, say, 48 hunnert away from a location. 

Dibs – Calling dibs is how you reserve something. If you’re thinking of hiring a car for your time in Chicago, you will become familiar with the term. Dibs is used by locals to claim parking spots, especially in the winter when snow must often be shovelled for residents to park. 

The ‘L’ - The Chicago underground metro system. 

The Red Hot – Chicago's own hotdog variant

Transport in Chicago - Getting Around Chicago, Illinois

Chicago’s expansive transport network, the CTA, has made public transport the most popular way to get around, with most navigating the city on its trains and buses every day. A single bus fare costs around $2.25, while a single ride on the underground metro system comes to approximately $2.50.  

Disposable passes can be purchased via L station vending machines which accept both cash and card. As well as single ride passes, the CTA offers 1 day, 3 day, 7 day and even 30 day passes, ranging from $5-$75, which can save you money if you know you’ll use the CTA multiple times during one trip. For those who prefer a paper-free ticket, Ventra Cards are available from Ventra vending machines, online or at selected retail locations. Want to have all your cards in one place? By downloading the Ventra App, your Ventra card can be added to your Apple, Samsung or Google phone’s wallet.  

Made up of 8 lines, navigating the L system can seem daunting, but with a simple colour coded key, it’s easy to get the hang of. The 8 lines are: Red line, Blue line, Brown line, Green line, Orange line, Pink Line, Purple Line, and Yellow Line, all of which connect inner Chicago with the suburbs, with useful links to both O’Hare and Midway airports. Planning a commute is simple with the CTA app which offers live service updates and allows users to track bus and train arrival times on a city map.  

Chicago’s grid layout makes walking an easy and popular way to get around. The Divvy bike share programme also offers convenient and eco-friendly travel, with over 500 docking stations across the city and a 30-minute rental at just $3. If you’re looking for a more scenic route around the city, consider hopping on the Chicago Water Taxi for views of the infamous skyline.  

Chicago Map

Now you’re up to speed on all the Chicago basics, have a look at our wide range of corporate serviced apartments in Chicago and contact our friendly team to book. It’s also worth checking out some more famous things to see in Chicago before you jet off!