Chicago city guide for business professionals

Discover Chicago’s rich culture, culinary delights, and architectural wonders and find out what to expect for your next business trip. Learn how to navigate the city easily.

Discover Chicago’s rich culture, culinary delights, and architectural wonders and find out what to expect for your next business trip. Learn how to navigate the city easily.

By Jessica Freedman

Chicago skyline by night with view of Lake Michigan

Welcome to your ultimate Chicago City Guide for business trips! Whether it’s your first time in the “Windy City” or you’re a seasoned visitor, this city guide will help you navigate this dynamic metropolis and make the most of your business trip.

Chicago, the third-largest city in the United States, is a major center for finance, technology, and commerce, ranking among the top eight business travel destinations in the USA. With its world-class conference centers, global corporate headquarters, and excellent infrastructure, the city attracts thousands of business travelers annually. From the impressive skyscrapers of the financial district to the innovative startups in River North, Chicago offers a diverse business landscape ideal for networking and professional opportunities.

This guide aims to help you explore Chicago efficiently and stress-free, allowing you to focus on your essential tasks and goals. With practical tips on transportation, accommodation, dining options, and the key business districts, you will be well-prepared for your next business trip.

Getting around Chicago

Transportation options

The Chicago Transit Authority (CTA) operates an extensive network of buses and trains that covers the entire city. Particularly convenient is the “L” train, which quickly and reliably takes you to major destinations. With over 140 stations and eight different lines, the “L” train is the backbone of public transportation. Daily and weekly passes are available and provide an affordable way to explore the city. Particularly useful is the direct access from O’Hare Airport to downtown, making long taxi rides unnecessary.

View of chicago elevated train by night

Services like Uber and Lyft are widespread and a convenient alternative, especially if you don’t want to deal with public transport schedules. Taxis are also easy to find and can be hailed at almost any street corner. Many hotels and office buildings have designated taxi stands, ensuring you always have a quick connection. For business travelers often under time pressure, these services offer flexibility and comfort.

For short distances or if the weather permits, you can also rent a bike or simply walk. Chicago is a bike-friendly city with many bike lanes and well-maintained sidewalks. The Divvy bike-share program offers a simple and affordable way to get around. With over 600 stations throughout the city, it’s a great option to quickly get from one meeting to the next or simply explore the city.

Navigating the city efficiently

To efficiently navigate the city, you should use a combination of public transport and ridesharing. Travel tech apps like Citymapper or Google Maps help you find the best routes and transport options. For business travelers frequently commuting between meetings, ridesharing services are often the fastest and most convenient choice. Many of these services also offer special business accounts, allowing you to bill rides directly through your company.

Chicago’s O’Hare International Airport is one of the busiest airports worldwide. To avoid long lines and delays, it is recommended to arrive early and use curbside check-in. For baggage drop-off, you should be at the airport at least one hour before departure, as this closes 45 minutes before the flight.

Access to lounges like the United Club in Terminal 2 or the American Admirals Lounge in Terminal 3 is worthwhile for business travelers. These provide a quiet work environment, complimentary refreshments, and comfortable facilities. Popular spots at the airport include the Billy Goat Tavern, the Bubbles Lounge, and the Garrett Popcorn Shop, whose products make great souvenirs. This can make the wait at the airport more pleasant.

Passengers waiting on line at Chicago O'hare airport

Chicago city guide – business districts

The Loop

The Loop is the heart of Chicago’s business world, home to numerous financial institutions, major companies, and conference centers. Here you’ll find the headquarters of many banks and financial service providers. A walk through the financial district offers an impressive view of the iconic skyscrapers that define Chicago’s skyline. The architectural diversity, ranging from historic buildings like the Rookery Building to modern skyscrapers like the Willis Tower, is impressive.

Many multinational companies have offices in the Loop, making it an ideal place for business meetings and networking. The Chicago Board of Trade, one of the largest and oldest trading venues in the world, is also located here.

McCormick Place, the largest convention center in North America, is nearby and a popular venue for trade shows and conferences. Numerous international events are held here annually, attracting business travelers from all over the world. The proximity to downtown hotels and restaurants makes it easy to network or relax after a long conference day.

River North

River North is known for its trendy restaurants, bars, and boutique hotels, making it a perfect place for networking and relaxed business dinners. Some of the most well-known restaurants include RPM Steak and Bavette’s Bar & Boeuf. They not only offer excellent cuisine but also an atmosphere ideal for business discussions. River North also hosts a variety of art galleries and design studios, giving the district a creative and inspiring character.

Many hotels in this area also offer well-equipped conference rooms and business centers, perfect for meetings and presentations. The proximity to major business districts and attractions makes these hotels particularly attractive for business travelers.

Man on Chicago river walk by night

Accommodations in Chicago

Business-friendly hotels

When choosing your hotel, you should consider the proximity to your business appointments and good public transport connections. A hotel in the city center provides you with the flexibility to quickly and easily reach your appointments and relax after a long workday, which is great for improving mental health when traveling for business.

Favor hotels that have amenities you need for a successful business trip, including conference rooms and fast internet connections. Choose hotels with a wellness center and several restaurants suitable for business meals to help make sure employees have a good work-life balance.


For a quick but impressive lunch with business partners, we recommend restaurants like The Gage or Lou Mitchell’s, which stand out for their excellent cuisine and central location. The Gage, a popular bistro on Michigan Avenue, offers a mix of classic and modern American cuisine in an elegant yet relaxed setting. Lou Mitchell’s, an iconic breakfast and lunch spot, is known for its traditional American dishes and warm atmosphere.

For evening business dinners, elegant restaurants like the Girl & The Goat are ideal, offering a top-notch menu and a stylish ambiance. Alinea, one of the few restaurants in the USA with three Michelin stars, provides a unique culinary experience that is sure to impress (if you’re lucky enough to get in, tables book up to 3 months in advance). Girl & The Goat, run by the renowned chef Stephanie Izard, is known for its creative and delicious cuisine, offering a casual yet upscale atmosphere.

If you want to impress clients or business partners, rooftop bars like those at LondonHouse or The J. Parker are ideal. They offer excellent drinks and a breathtaking view of the city. LondonHouse Chicago, with its spectacular view of the Chicago River and skyline, is a popular spot for informal business meetings. The J. Parker, located on the roof of the Lincoln Hotel, offers a stunning view of Lincoln Park and Lake Michigan – perfect for a relaxed evening after a long workday.

Chicago city guide: wrap-up

Chicago is a vibrant city that has much to offer business travelers. From top-notch hotels and restaurants to modern conference centers and premier business districts – the city is well-equipped to meet all the needs of business travelers. With a variety of transportation options, whether through public transport, ridesharing services, or on foot, it is easy to move around efficiently and stress-free.

Whether at a business meal in a top-tier restaurant, a relaxed moment in a luxurious hotel lounge, or exploring the architectural wonders of the city – Chicago will not disappoint. Explore and enjoy everything this lively city has to offer!

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