City Guide – Chicago

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With over 75 distinct neighborhoods in Chicago, The Windy City is one of the U.S.’s most diverse and exciting places in terms of history, sports, arts and culture. Whether it’s the ivy walls of Wrigley Field or the iconic spears of Willis (Sears) Tower, the city is home to an unending list of historic landmarks and legends that attracted a record-breaking 55.2 million visitors in 2017. Named Bon Appetit’s 2017 Restaurant City of the Year, Chicago now finds itself repositioned as a culinary capital, attracting chefs, restaurateurs, and foodies from around the world.

Home to the largest exhibition space in North America, McCormick Place, Chicago plays host to some of the world’s biggest conferences, including Oracle’s Modern Customer Experience, Techspo, and Digital Summit Chicago. With an overwhelming and ever-growing list of world-class hotels, restaurants, and attractions, the city can be tough to navigate due to the volume of options alone. We put together this list of recommendations for future visitors, planners, and professionals to help make the most of their visit.

Where to Stay in Chicago


  • Named for the restored Georgia Gray marble that adorns the building, the Kimpton Gray Hotel exemplifies a classic yet cool, modern elegance. The hotel offers all the amenities, plus an in-house hair salon and yoga classes. Additional features include an Argentinean-inspired rooftop lounge and restaurant, a vintage encyclopedia set for guests to enjoy in the library-themed lobby bar, and complementary bikes for guests. The hotel is pet-friendly as well, for those of you travelling with four-legged friends!
  • Located just across from Millennium Park, the Chicago Athletic Association Hotel takes its name from the historic, members-only athletic club that once occupied the building. Housed in a stunning 122-year-old Venetian Gothic building, the hotel boasts a game room, multiple restaurants, and various meeting and event spaces. The hotel is worth a visit just for the architecture and design alone!

River North

  • The Dana Hotel and Spa is a boutique hotel in the River North Gallery District, steps away from the Magnificent Mile and the Loop. The rooms here are modern and sleek with floor-to-ceiling windows and balconies offering incredible city views. Amenities include a widely acclaimed restaurant and a rooftop lounge, luxury spa, gym, and event space.
  • Among the historic mansions of Chicago’s Gold Coast, The Langham is a five-star hotel offering luxuries such as an onsite spa, indoor swimming pool, variety of restaurants and cafes with spectacular views, and a complementary luxury car service. Rooms each come with floor-to-ceiling windows and rainfall shower heads; lake views and private terraces are also available by request.

South Loop / McCormick Place

With both the Hyatt Regency and Marriott Marquis in immediate proximity to McCormick Place, conference goers have two great options for convenience and quality. Here are some alternative options, just in case:

  • Just a short cab ride away from McCormick Place is the stunning Blackstone Hotel, a 1910 beaux arts building across the street from Grant Park with incredible views of Lake Michigan. The Blackstone is a historic architectural icon, updated and fitted with all modern amenities including a gym, business center, and a number of private meeting rooms, plus an acclaimed Spanish restaurant, luxurious lounge, and Market Cafe.
  • The historic Hotel Blake is another example of Chicago’s exceptional ability to marry its past and present. The hotel, housed in the former 19th-century headquarters of the Morton Salt Company, offers a chic and modern interior to compliment its storied facade. The hotel is only a ten minute cab ride from McCormick Place, and offers a classic American restaurant, business and fitness centers, and meeting spaces for small to mid-sized groups.

West Loop

  • Housed in a former belt-manufacturing warehouse, the Soho House is in close proximity to some of the city’s best bars and restaurants. That said, you might never want to leave after experiencing its unbelievable rooftop pool, in-house film screening room and adjacent bar (perfect for an unforgettable private event), in-house spa, and variety of restaurants and lounges. A visit to the Soho House is a holiday in its own right, and will no doubt make you forget that you’re even in a hotel.

Wicker Park

  • The Robey’s Art Deco architecture is just one of the hotel’s unique features, including a rooftop pool and adjacent Cabana Club, French-American cafe, and 180-degree views of the city skyline. It’s chic, modern design is just one of the carefully crafted elements that make the Roby a must for anyone interested in checking out one of Chicago’s coolest neighborhoods.

chicago at night

Where to Eat, Drink, or Host an Event in Chicago

Once synonymous with hot dogs and deep-dish pizzas, Chicago has redefined itself as a world-class culinary capital, with a growing list of Michelin-starred restaurants help add to the spotlight. In a city of over 5,000 restaurants, it’s impossible to put together a list of recommendations without leaving out a number of incredible options. Alas, we gave it a go!

Private Group Events & Dining

  • Offering 21st century meals in a historic 19th century building, Sepia is a favorite of celebrities and locals thanks to the palpable attention to detail in both the food and the environment. The menu is seasonal and rooted in traditional practices, turning classic Chicago dishes into a beautifully inventive menu. West Loop – $$$
  • Two-Michelin-starred Acadia‘s modern, sleek interior design is the perfect setting for the thoughtful seven-course “tasting experience” and pairing on offer. Inspired by coastal Maine, the menu exemplifies the role of modern global influences in New American dishes. Ideal for those looking to enjoy one of Chicago’s unique fine-dining experiences close to McCormick place. South Loop – $$$
  • The Chicago Firehouse got its namesake from its history as a former home to Engine Company 104 of the Chicago Fire Department. With a floor to ceiling windowed solarium and adjacent patio, the atmosphere is relaxed and inviting. Offering classic American dishes with an impressive wine and cocktail list, this is an excellent venue for both small party dining and private group events. Just a short cab ride away from McCormick Place, the Chicago Firehouse offers incredible service to add to the already impressive experience. South Loop – $$$
  • With influences from Portugal, Spain, Lebanon, and the Mediterranean, Eden’s Creative New American fare has received well-deserved praise since its 2016 opening. Using local, seasonal ingredients – many grown onsite in their urban greenhouse garden – this charming space is light, rustic and inviting. Their menus include exciting options such as umami donuts, and herb and porcini spätzle; they also offer a beautiful Chef’s Counter tasting menu with pairings. West Loop – $$
  • Located on the 20th floor of the Conrad Hotel, Baptiste & Bottle brings together New American cuisine and bourbon-focused craft cocktails. The incredible private dining room with floor-to-ceiling windows offering stunning views of Chicago skyline to the south. River North – $$$
  • For a casual, quintessential Chicago experience, look no further than Revolution Brewing. Their brunch, lunch, and dinner menus are full of crowd-pleasers and their beer list has something for everyone, including seasonal flavors that you’re unlikely to find anywhere else (hibiscus ale, yes please!). They have event spaces for groups of all sizes, and even offer discounts to registered non-profits. Logan Square – $$

Small Party Dining

  • We have to start this list off with Alinea, Chicago’s first and only restaurant to be awarded three Michelin Stars. This is not the place to go for a traditional dinner, but instead serves as an epicurean paradise. Featuring a single, seasonally driven tasting menu of between 18 and 22 courses, Alinea is an experience, more so than a restaurant. Having featured in an episode of Chef’s Table, on top of its numerous awards, this is not an easy table to get – so we advise you to book well in advance! Lincoln Park – $$$$
  • Since its opening in 2010, The Girl and the Goat has maintained its reputation as one of the hottest and best known restaurants in town. It’s open kitchen and rustic feel offer guests a warm but bustling environment, and former Top Chef winner Stephanie Izard’s eclectic menu is big on flavor and global influences. West Loop – $$$
  • Name Best New Restaurant by Chicago Magazine, Owner and Executive Chef Noah Sandoval’s Oriole has taken the stuffiness out of fine-dining and replaced it with a modern, open-design experience that has gained two Michelin stars since its opening in 2016. With a remarkable sixteen-course menu and carefully crafted beverage pairing, Oriole offers a unique dining experience that lives up to the hype. West Loop – $$$$
  • If you’re looking for a hip, casual experience paired with incredible food and cocktails, look no further than Michelin-starred Longman & Eagle. Don’t let the laid back, saloon-like vibe fool you – the menu is chock-full of unique and creative dishes, and they boast an impressive whiskey collection that includes rare and vintage bourbons. They also have spaces for private events, perfect for a happy hour or group tasting, and offer a small number of chic hotel rooms above the restaurant for those who need a power nap between rounds. Logan Square – $$

chicago mural what to see

What to See/Do in Chicago

Art Institute of Chicago– Housing more than 300,000 artworks from around the world, the Art Institute of Chicago is a collection of mediums and epochs for art lovers and neophytes alike. Their permanent collection includes well-known works such as Edward Hopper’s Nighthawks, Georges Seurat’s A Sunday on La Grande Jatte, and Grant Wood’s American Gothic, while rotating exhibits range from Japanese Print Artists to Scandinavian Designers. With a variety of cafes and events, the Institute offers something for everyone.

Chicago Architectural Foundation River Cruise – There’s no better way to see the city then by this ninety-minute tour of Chicago’s history and architecture. Tours are available during both daytime and evening hours, and even offers an option on weekends specifically for those with an interest in photography.

The Field Museum – One of the largest natural history museums in the world, the Field combines science and education for visitors of all ages. Exhibits on mummies, pirates, dinosaurs, plants from around the world, and precious gems, plus a planetarium (!) offer visitors a variety of options.

The Green Mill – You can’t talk Chicago without talking jazz. A former hangout of Al Capone, this Uptown lounge survived prohibition to become one of the city’s most historic jazz clubs, playing host to the likes of Billie Holiday and Benny Goodman. Following a late-eighties revival by its current owner, the Mill has become an icon of Chicago jazz, and has featured in a number of films including “Oceans 12” and “High Fidelity”.

Lakefront Trail – This 18-mile path along the western shore of Lake Michigan connects neighborhoods throughout the city, crossing through beaches, trails, and parkland. The various panoramic views of the city and lake are not only free to the public, but also available by car, bike, or on foot. Serious Instagram-worthy opportunities on the Lakefront Trail!

The Second City – Bill Murray, Gilda Radner, John Belushi, Stephen Colbert, Steve Carrell, Tina Fey, Amy Poehler… the list goes on – all got their start at The Second City. If you’re looking for laughs, or the bragging rights to say that you saw (insert future SNL star’s name here) before they were famous, look no further than this Lincoln Park theatre.

Willis Tower Skydeck – We try to avoid the major tourist destinations, but this is a must. Located on the 103rd floor of Willis Tower, you will find no better view of Chicago and its neighborhoods than the one from the Willis Tower observatory. Avoid the crowds and experience the skyline during the Skydeck’s evening hours; from October through February it’s open until 8pm, and until 10pm from March through September.

Chicago is well-known but full of secret gems, which is why visitors who travel for business often extend their stay to enjoy some of the city’s many offerings. The city is a veritable playground for event planners, visitors, and locals alike. Steeped in history yet perfectly balanced with modernity, there is a reason Chicagoans are so proud of their home city. With no shortage of transportation options, including one of the country’s largest airports and public transportation lines, navigating the Chicago is easy enough with the right guide.

chicago city guide lakeMarcela Ricci, Certain

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