Whether you’re visiting Chicago for the 2019 Global Business Travel Association (GBTA) Convention or for another business trip altogether, you’re in for a treat. Voted Best City in America by Condé Nast Traveler in 2017, the Windy City is a vibrant and friendly destination with iconic architecture and plenty of charm. Its location, wide range of amenities and excellent infrastructure make it the perfect host city for business meetings both large and small.

To learn more about how to get the most of your stay in this incredible metropolis, read this useful city guide American Express Global Business Travel has put together.

For those heading to the GBTA conference, be sure to stop by and visit us at Booth 2021, where we will be giving you the opportunity to take part in creating a live work of art, one photo at a time. Snap a picture, tag us on Instagram or Twitter using our #momentsthatmatter hashtag and pop by Booth 2021 to see your pictures flying into place on the mosaic.

Arriving in Chicago
The majority of international flights land at Terminal 5 of the busy O’Hare International Airport, where collecting luggage and clearing immigration and customs can take up to two hours.

Taxis are readily available upon exit and the city center is around 45 minutes away. If you intend to travel to the center using the ‘L’ train, Metra train or a hire car, be advised that the free Airport Transit System to these points is being upgraded and will be replaced by frequent shuttle buses until autumn 2019.

Getting around
Chicago is a great walking city with an easy-to-navigate downtown grid, centered at the junction of Madison Street and State Street. Taxis are plentiful, but it’s worth downloading the hail and pay app CHICABS.

The Chicago Transit Authority (CTA) operates more than 100 bus routes and eight ‘L’ lines. With 145 stations and two 24-hour lines, the ‘L’ connects the city both above and below ground and is perhaps the easiest way to travel. One- ($10) and three-day ($20) combined bus/rail CTA passes offer great value.

From some locations, water taxis offer a convenient mode of transport. If you have some free time, the bike-sharing program Divvy offers a fun way to explore the Lake Michigan shoreline.

Where to stay

  • Recently refurbished, the Fairmont Chicago is conveniently situated at the epicenter of the Loop, the city’s central business district.
  • For something more boutique, The Robey – located in a striking wedge-shaped Art Deco building – contains plenty of original 1920s touches.
  • The Hyatt Regency McCormick Place, with spectacular views of the city and Lake Michigan, is ideal if attending an event at McCormick Place convention center. (GBTA Convention 2019, anyone?)
  • LondonHouse Chicago, a part of the Hilton family, offers a sophisticated ambiance and some of the best views from its rooftop lounge.

Where to eat

When it comes to food, Chicago is perhaps most famous for its steaks and deep-dish pizzas. Gibsons Bar & Steakhouse is a meat-lovers’ institution, and is also famous for its mammoth desserts, while Pequod’s Pizza’s signature caramelized cheese crust is a must-try.

Vegetarians should head to Clever Rabbit, an inventive, “root to leaf” restaurant that also caters for those needing a protein fix. Try Fat Rice for tasty Asian fusion and Calumet Fisheries for legendary smoked seafood. Despite its two Michelin stars, Oriole remains devoid of pretension and is one of Chicago’s best-kept secrets, while the three Michelin-starred Alinea offers an unconventional experience, with mind-blowing food that keeps it high on “The World’s 50 Best Restaurants” list.

Where to meet friends or colleagues

  • The Green Mill, once frequented by Al Capone, mixes cocktails with old-world charm and great jazz.
  • The Press Room specializes in wine – by the glass or bottle – served with charcuterie and cheese.
  • At Hopleaf, with its relaxed vibe across multiple bars, it’s all about the beer… on draft, in bottles and cans.
  • Soho House is home to the cozy Fox Bar. It’s open to nonmembers and is renowned for seasonal drinks, such as rhubarb-infused Aperol.
  • If you are out to impress, head to The Aviary, where cocktails are presented in surprising ways, such as Manhattans served inside giant ice globes.

*The legal age to drink in Chicago is 21. Drink responsibly.

What to do

Time to kill before your return flight? Here are five great ways to spend it:

  • Experience the exhilarating panorama from a glass-floored viewing box on the Skydeck, 103 floors up the Willis Tower.
  • Catch a baseball game and appreciate the retro charm of Wrigley Field.
  • Enjoy a show at comedy club The Second City, a Chicago institution that launched the careers of Bill Murray and Tina Fey.
  • Tour the Pullman Historic District, built in the 1880s for railroad workers.
  • Visit the International Museum of Surgical Science and check out the 19th-century iron lung and collection of post-lobotomy skulls.