Business travel expert Mark Frary's travel guide to Chicago. Need a great value hotel? Want to know the city's movers and shakers on Twitter? Looking for ways to spend your down-time in Chicago? The answers are all here.

President Obama's adopted home town is one of the USA's business powerhouses – with the Head Quarters of Boeing and McDonald's situated in the city. But Chicago is also a cultured place with inspiring modern art installations and a skyline of architectural gems to admire.

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Chi-Town, as Chicago is often known, is a centre of innovation; the city had the second highest number of companies on the Inc. 5000 list of fast-growth companies in 2014. And Chicago mayor Rahm Emanuel has committed to doubling the size of the city’s tech economy to 80,000 jobs within the next decade.

Tech may be in, but transport and distribution have been a central plank in Chicago’s success over the past century and a half. The city is a busy container port, with links to the Atlantic – via the St Lawrence Seaway – and to the Gulf of Mexico – via the Mississippi. Chicago is also at the intersection of six of the seven major US freight rail networks.

With these excellent links, it’s no surprise that Chicago is a major manufacturing hub. Food giants McDonald’s and Mondelēz International (the conglomerae that owns Cadbury) are headquartered here, along with airplane manufacturer Boeing.

Express Essentials

Chicago O’Hare airport (ORD) is the seventh busiest in the world in terms of passenger traffic, handling almost 70 million people every year. It is linked from Heathrow by four airlines: American Airlines (3 x daily Boeing 767/777 services), British Airways (2 x daily on 747/777), United Airlines (3 x daily on 767) and Virgin Atlantic (daily on A330). Typical journey time is 8hours 30mins.

O’Hare is 17 miles north west of downtown Chicago – which will set you back approximately  $40 in a taxi, with the journey taking anywhere from 25 minutes to more than an hour. If cost-cutting and punctuality are more important than privacy, take the L train(elevated – though not all lines are raised above ground level); it approximately  $5 and takes 45 minutes. Shared shuttle buses also operate regular services and costs between  $25 and $35.


Chicago’s web-like public transport system, with lines radiating out from the centre, is one of America’s most comprehensive, and the L train system serves more than 140 stations around the city. A single ticket costs $2.25, and a day pass $10.

Taxis are widespread and charge $3.25 flagfall and $1.0 for subsequent miles. The city was also one of the early locations for Uber.

Culture Shot

Chicago has loomed large in many music genres: Kanye West, R Kelly, Smashing Pumpkins (not to mention the eponymous Chicago) all hail from the city. Meanwhile, as the birthplace of house music, Chicago is where Ron Hardy and Frankie Knuckles introduced clubgoers to the new sound in the 1980s. The Warehouse – which lent its name to the genre – has long gone, but you can still hear great house being played in the city at venues like basement lounge Spy Bar and The Shrine.

Chicago invests heavily in public art and has a number of fine sculptures around the city, including the Chicago Picasso on Daley Plaza; a 15m high monumental work by the Cubist artist installed in the late 1960s.

Daley Plazza

Meanwhile, the Art Institute of Chicago is one of the world’s greatest museums. Its stunning permanent collection includes Matisse's Bathers by a River and Magritte's Time Transfixed.

Keep your eyes open on a business trip, and you’ll enjoy highlights of the famous Chicago skyline as you move between meetings. Some of the most important architecture – including the Seagram Building and the SR Crown Hall at the Illinois Institute of Technology – is designed by the German-born modern architect Mies van der Rohe.


The Black Book

Downtown Chicago’s average hotel rate in the year to March 2015 was $150.40.

The Langham is a recent addition to the city’s hotel portfolio but has quickly become a business favourite. Housed in another Mies van der Rohe building – the AMA Plaza skyscraper – the Langham sits in a perfect location by the river in downtown Chicago. The style is understated and modern (think: neutral colours, touchable textiles and dark woods) and the service is hard to beat. From around $330 a night plus taxes).

Hipster restaurant Longman and Eagle, which serves up nose-to-tail American food – such as pork chop and belly with asparagus – branched out into hotel rooms a few years back. Spend the evening with a client in the whisky bar before heading upstairs into one of its six bargain rooms.


And on the corner of Milwaukee and Fullerton avenues, you will find Gaslight Coffee Roasters. This industrial shabby chic coffee shop is a popular haunt for java-lovers wanting a pastry and some Wi-Fi

Business Insiders

Want the inside track on Chi-Town? Check out these Chicagoan social media influencers to get the lowdown:

  • Mina Im, aka Chicago Food Girl, a lover of all things glitz, glam and sparkles, writes about places to eat in ChiTown as well as fashion, art and travel.
  • Business publisher Crain’s Chicago @CrainsChicago is a rich source of business info on the Windy City.
  • Delve inside the rich history of the city with the Chicago Tribune’s photo archives@vintagetribune 
  • The Tribune’s social media manager @ScottKleinberg is another must-follow for visitors to the city – he brings a mix of business, sport and lifestyle.
  • Visit Chicago Music Magazine for gig details, reviews and tips on Chicagoan bands to watch for the future.


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