The forgotten gem of the Midwest. For those who have been to or are from Chicago, the Windy City holds a special place in their hearts. Chicagoans take great offense at “fly-over city” being applied to the Second City, which is smack-dab in the heart of America. If you are going there for business, do not fret: The heartland metropolis has a wealth to offer that will leave you wanting more, guaranteed.
Where do most executive getaway articles begin? You guessed it, where to lay your executive head. The Chicago Loop (coupled with the rest of downtown) is the second largest business district in the country. Only Midtown Manhattan tops it in terms of scale. Major corporations such as Chase Bank, Exelon, Aon Corp., United Airlines, Blue Cross and Blue Shield Association and Sidley Austin and Morton Salt are all headquartered in the Loop. So where will you likely be laying your head? The Loop.
By far one of the best business hotels in the Loop is the Wyndham Grand Chicago Riverfront. Located on the edge of Chicago’s Theatre District, the Wyndham features 357 rooms with all the amenities you could ask for at very reasonable rates despite its first-class status. Another solid choice in the Loop is the Fairmont Chicago, Millennium Park. Nearly double the size of the Wyndham in terms of rooms (687), this David Rockwell-designed hotel is a stunner aesthetically. If you want to splurge a bit, check out the Fairmont Gold Concierge Level, which includes a private lounge and reception area with sweeping views of Lake Michigan.
If a direct location in the Loop is not a priority and you want to make this business trip one to never forget, the Waldorf Astoria Chicago is your only destination. Located in the swanky Gold Coast neighborhood, and a short distance from the Loop and downtown, the hotel features a top-notch restaurant (Balsan), an indoor lap pool, a world-renowned spa and sleek rooms. There is a plethora of conference space and from an amenities perspective, there is not a single thing missing in this hotel. The Astoria has truly taken business travel to another level with this property.
Now that you’re settled in and presumably exhausted after a long day in meetings, workshops, etc., it’s time to experience that one-of-a-kind Chicago dining that everyone raves about. Narrowing down our suggestions to fit a tight piece such as this is challenging to say the least. With that said, no trip to Chicago is complete without a taste of their infamous deep-dish pizza. New York versus Chicago is in full swing here, and Pequod’s Pizza in Lincoln Park will give any New York pizzeria a serious run for their money. Deep doughy pizza, caramelized crust and an assortment of toppings at Pequod’s might leave you with some calories to burn that next day, but they are entirely worth it.
Taking you from pizza to one of the world’s finest dining establishments, Alinea is the place to take only your most highly regarded colleagues and clients. Oh, and make reservations months ahead of time as this three-Michelin-starred restaurant is always in hot demand. Dishes change based on the season, but the edible balloon and tabletop dessert are present year-round. Another excellent choice for special guests is Maple & Ash. This Gold Coast steakhouse has been churning out creative twists on old, steakhouse classics for years. The wine list is extensive, and you might even see some Chicago celebrities/sports stars as well.
If you’ve got a more casual night, a bit more upscale than pizza, perhaps with a colleague or someone you do not need to wine and dine, go to Frontera Grill and Topolobampo. A bit of a mouthful, but mouths are filled here with south of the border fare in a casual, festive setting. This is the type of place you are angry at when 11 p.m. rolls around and you’re in full swing but need to wake up for your flight at 6 a.m. Great food, fantastic atmosphere.
If you’re lucky, dining will not be the only thing occupying your free time. Perhaps a nightcap will be in order. Chicago is not only a foodie town but a boozy town. You’ll get a real taste of the speakeasy culture at The Violet Hour, a hip cocktail lounge without a sign, but with a line–always. Once inside, the wait is most definitely worth it. The Sportsman’s Club is another Chicago staple, more informal but interesting, especially in the summer when top chefs from around the city flock to the patio to host cookouts. The food is otherworldly, and $20 will fetch you a hefty plate and one drink.
Finally, what’s to see in this city? Most business trips will yield the equivalent of one full day (a couple half days) or two if you’re lucky. A must, must, must for sightseers is the Art Institute of Chicago. A world-class art museum—and literally one of the oldest in the U.S.—it boasts collections ranging from modern to quite ancient. Don’t be surprised when a Gauguin, Manet or Picasso await you. The iconic lion statue outside is also an obligatory spot for a selfie pic.
Our next recommendation is neighborhoods. As generic as it sounds, Chicago neighborhoods are impressive. You’ve got Chinatown, Greek Town, Little Italy and a range in between. Immigrants from everywhere, similar to New York and Los Angeles, came to Chicago in search of a better life. Their culture arrived with them and is on full display in the Windy City.
To wind it up, the aquarium! You can take in the Shedd Aquarium, located on Chicago’s Museum Campus, where a charming backdrop of the lake welcomes visitors to a dazzling display of penguins, whales, sharks, piranhas, stingrays, dolphins … the list is endless. One of the country’s premier aquariums, this is a great option for burning a morning or afternoon before a flight.
We hope this post has been fruitful, and most of all, entertaining for your next business trip to the wonderful, Windy City!