Between Meetings: 10 Things to Do in Chicago

By: Claire Bullen

June 24, 2014

Travelling to Chicago for business? There are a few things you should know if you’ve got an hour or two between meetings to spend exploring this Midwestern locale. First of all: no, it’s not called “The Windy City” because of its weather (though you may enjoy some lakefront breezes). Another: Chicago pizza is real pizza, and it’s as delicious as they come. And finally: this is a destination with a huge range of offerings, from museums and parks to restaurants and famous landmarks. You only need an hour to discover some of the city’s best sights – don’t miss these 10 things to do in Chicago.


10 Things to Do in Chicago | Giordanos Pizza

Giordanos Pizza ©Flickr/Eric Chan

Chicago-style pizza may ignite debates between locals and East Coasters as to whether it counts as “real” pizza, but no matter your opinion, you can’t argue that the city’s two-inch-high “pies,” filled to bursting with sauce and molten cheese, are utterly delicious. Head to Giordano’s in The Loop for an authentic (and filling) slice of this local speciality.

Millennium Park

10 Things to Do in Chicago | Millennium Park

Millennium Park © Flickr/Vincent Desjardins

New York may be the Big Apple, but Chicago can claim ownership to The Bean. Otherwise known as “Cloud Gate,” the metallic sculpture by Anish Kapoor, located in Millennium Park, became an instant Chicago hit when it debuted to the public in 2006. The park, which has been lauded for its innovative urban planning, has other public sculptures and installations on display, as well as abundant green space made for lounging. No wonder it ranks high on our list of 10 things to do in Chicago.

The Art Institute of Chicago

10 Things to Do in Chicago | Art Institute of Chicago

The Art Institute of Chicago © Flickr/Phil Roeder

One of the world’s finest art museums, The Art Institute of Chicago has a staggering 300,000 works in its collection, including Edward Hopper’s “Nighthawks”, Grant Wood’s “American Gothic”, and Georges Seurat’s “A Sunday on La Grande Jatte”. Take inspiration from Ferris Bueller and devote some time to browsing the galleries.

Intelligentsia Coffee

10 Things to Do in Chicago | Intelligentsia Coffee

Intelligentsia Coffee © Flickr/Bobbi Bowers

If you’ve been through meeting after meeting, you’re probably going to need a coffee break. Luckily, you don’t have to trek too far to find good java. Intelligentsia Coffee, first opened in the city in 1995, roasts its own beans and approaches its coffee with a perfectionist’s eye. The result: perfectly balanced, frothed, and latte art-crowned works of coffee mastery.


10 Things to Do in Chicago | Blackbird

Blackbird, Chicago © Andrea Donadio

Since opening in 1997, Blackbird has been a stalwart of the Chicago fine dining scene, even winning two James Beard Awards in the process. That doesn’t mean it’s inaccessible, though: solo travellers looking for a nice lunch out can opt to sample its three-course prix fixe lunch menu, available for just $25. Come expecting avant-garde fare courtesy of Executive Chef Paul Kahan.

The Aviary

10 Things to Do in Chicago | The Aviary

Cocktails at The Aviary © Flickr/John Joh

Mention Grant Achatz’s name to any foodie and they’ll likely gasp and start muttering about the wonders of Alinea and Next, his showstopper Chicago restaurants. While reservations fall on the “near impossible” end of the difficulty spectrum, travellers can still taste some of his magic at The Aviary cocktail bar. The angle here is to approach drinks with a curious, culinary perspective, with the result being nothing short of molecular gastronomy. An insider tip: The Office, a bar-within-a-bar located downstairs, offers a cosy, speakeasy atmosphere.

The Willis Tower Skydeck

10 Things to Do in Chicago | Skydeck

Willis Tower Skydeck © Flickr/daveynin

Though most Chicagoans will still insist on calling it the Sears Tower, the Willis Tower (renamed in 2009) is a must-visit Chicago site. Ranking as the second tallest building in the western hemisphere, the landmark’s 103rd-floor Skydeck lets travellers appear to walk into midair, courtesy of its glassed-in viewing platforms. While those with a fear of heights may want to avoid, the stunning views of the city are well worth the momentary butterflies.

The Chicago Riverwalk

10 Things to Do in Chicago | Chicago Riverwalk

The Chicago Riverwalk © Songquan Deng/iStock/Thinkstock

Another favourite (and less vertigo-inducing) perspective on the city can be had from the Chicago River. While the waterway plays host to a number of architecture-themed boat tours, those with a bit less time to spare can take in the sights from the Chicago Riverwalk. Admire the city’s spires, and stop for a quick nibble at one of the Riverwalk’s many cafes.

The Magnificent Mile

10 Things to Do in Chicago | Magnificent Mile

The Magnificent Mile © dibrova/iStock/Thinkstock

Chicago’s Fifth Avenue (or perhaps its Champs-Élysées), The Magnificent Mile refers to the northern stretch of Michigan Avenue, one of the city’s central arteries. The architectural sites continue for those with an eye for design – you’ll stroll past icons like the Hancock Center and Wrigley Building – but The Magnificent Mile is a particular draw for those looking to do some shopping. Whether you want to blow off some steam or bring home some souvenirs, there are hundreds of upscale retailers to choose from.

North Avenue Beach

10 Things to Do in Chicago | North Shore Beach

North Shore Beach © Jesse Kunerth/iStock/Thinkstock

Chicago may be located right in the middle of the Midwest, but that doesn’t mean it doesn’t have some sandy stretches to relax on. Pretty Lake Michigan is ringed by pretty beaches that draw crowds during the summer months – or pretty much anytime post-thaw. The centrally located North Avenue Beach is arguably the most popular of the lot, with golden sand and unrestricted swimming.

Virgin Atlantic operates a seasonal direct service to Chicago from London Heathrow. Book your flight today.
What are your top 10 things to do in Chicago? Have you visited any of the landmarks mentioned here? Let us know in the comments section below.

Written by Claire Bullen


Claire Bullen

Claire is a born globetrotter: before relocating to London, she spent time in New York, Paris, Philadelphia, Chicago, and San Francisco. When she's not in pursuit of the next exciting meal, she can be found haunting indie bookstores and sketching outdoors. Follow Claire @ClaireMBullen

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