Stopover Guide: 24 Hours In Chicago

11 March 2016
Read Time: 3.7 mins

Words by Tijana Jaksic

Chicago has long been a hub for all things industry and commerce. With a central US location, a number of swanky new high profile hotels and an extensive airline service – O’Hare International Airport is one of the busiest airports in the world – this global financial centre continues to grow from strength to strength.

But it doesn’t have to be all work and no play. Beyond the office buildings and financial hubs of the Loop, a business trip to Chicago is made all the more enjoyable with a spare day to investigate. Here’s a guide to the Windy City.

Where To Eat


For a satisfying and tasty kick-start to the day that won’t guzzle precious hours of time, swing by Eastman Egg Company. Specialising in delicious, hearty and rather extravagant sandwiches, it’s the perfect grab-and-go option.

Their claim to fame: that everything on the menu is made to order in under five minutes and the ingredients are all farm-fresh.

Word has it the “Scoundrel” is amazing – a meeting of egg, smoked turkey, white cheddar, wilted spinach and house spiced mustard on a fresh pretzel roll. The classic “Doc” is also a favourite – a warm fluffy ciabatta filled with cheese, bacon and egg. Lighter options include a fruit salad and granola, while the cookies are great for the road.

While you ‘wait’, try their single origin Irving Farm coffee blend. It’s roasted fresh weekly and is hailed one of the best local craft coffees around.


Sepia remains one of the West Loop’s most respected go-to business lunch spots still, nearly a decade on since opening its doors. Situated in the former site of a 19th-century print shop, the rustic decor is stylish yet warm and inviting – ideal for talking business.

With Michelin-star status and renowned chef Andrew Zimmerman at the helm, Sepia can seem pricey – but it is indeed an affordable option and one of the best-value Michelin-starred restaurants in Chicago.

Lunch is served Monday to Friday, consisting of exceptional starters and entrees, as well as a selection of gourmet sandwiches – think Thai chicken sausage, pickled carrot and daikon, cilantro and mint. A delectable range of sweets and an impressive wine list perfectly rounds out the menu.


For an iconic view that’s as entertaining for one as it is for a group, Sixteen is an old hand at the game of first impressions. Located on the 16th floor of Trump International Hotel and Tower, this Michelin two-star rated restaurant plates up modern American cuisine complemented by mesmerising Chicago panoramas.

Get the meeting started over a vintage wine, before moving on to the four-course tasting menu. Another hit for entertaining clients is the nine course blind tasting menu, which takes the fuss out of choosing.

Alternatively, enjoy a lower-key but still sophisticated outdoors option in the summer months at The Terrace at Trump, home to specially crafted food and cocktails – and breezy views that come completely unobstructed.

Looking for more US stopover guides? 

Stopover Guide: 24 Hours In Dallas

Stopover Guide: 24 Hours In Honolulu

Stopover Guide: 24 Hours In Los Angeles

Where To Stay

When contemplating where to stay in Chicago, the Renaissance Chicago Downtown Hotel is a top pick in the business-centric Loop neighbourhood, yet within reach of a number of chief sightseeing attractions including State Street and the Theater District.

Newly renovated, expect modern and contemporary rooms exuding chic, sophisticated design and modern conveniences. Many boast breathtaking skyline and river views.

When the laptop calls, retreat to the ground floor lobby bar and convivial stadium seating area to enjoy a more relaxed working environment. For matters requiring full concentration, opt for the swanky VIP lounge – it’s quiet and the lobby bar is right next door. An Artist Studio, Coffee Bar and Library offer an extra change of scenery.

Beyond business and bed, this premier hotel touts a spa, indoor pool, fitness centre and meeting rooms for a charge.

Where To Play

There’s no reason why you can’t squeeze in a few local attractions in your downtime. From cultural pursuits to natural escapes, there’s a plethora of possibilities at hand if you can sneak in an extra 24 hours.

An easy night-time attraction to squeeze in post-work is a trip to the theatre. Chicago’s thriving arts scene means there’s no shortage of ritzy shows and musicals lighting up the stage throughout the Theater District.

With a whole free day, consider delving into a different side of the local culture at a handful of the world-class museums. The Field Museum of Natural History and the Museum of Science and Industry are standouts – as is the impeccably stylish Modern Wing at the Art Institute of Chicago, dedicated to art of the 20th and 21st centuries including works by Pablo Picasso.

For a very different, much greener encounter with the local creative scene, spend an hour or two wandering the marvellous intertwining of gardens and public art displays at Millennium Park. Bordered by soaring skyscrapers, this is a thoroughly modern affair and a unique one, at that.

Those with a true eye for architecture may prefer a front row seat – complete with commentary – to a showing of Chicago’s most iconic buildings on a dedicated architecture tour by boat, cruising up and down the river.

For more city hustle and bustle, join the flock of shoppers descending on Michigan Avenue – more famously known as the ‘Magnificent Mile’ – for eight blocks worth of chic designer boutiques, towering shopping centres and iconic American department stores. A new suit is always a worthy buy.

Looking for one last iconic Chicago moment to relish before rushing back to the airport? Don’t miss Navy Pier. This atmospheric 50-acre playground beckons all ages with its restaurants, shops, museums and a giant Ferris wheel that juts out into the horizon – all colourfully sprawled along the sweeping shores of Lake Michigan.