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Exploring Chicago: A DMC's Guide for Incentive Travel

Updated: Oct 10, 2023

Chicago, an often-overlooked gem of an incentive destination, has claimed the title of the "Best Big City" by readers of Condé Nast Traveler for seven consecutive years. From its iconic skyline and renowned architecture to its spirited arts scene and diverse culinary offerings, Chicago offers a kaleidoscope of experiences that can transform a corporate event into an unforgettable adventure. With skyscrapers reaching for the clouds, the electric buzz of vibrant city streets, and a river that winds through a tapestry of history and culture, the Windy City boasts an unmatched combination of convenience, versatility, and excitement. Unlike the traditional notion of a relaxing resort, Chicago offers a different kind of allure that caters to go-getters and high performers. It's a city that pulses with energy, where every moment is a chance to explore, discover, and indulge. An astounding array of offsite venue options, from breezy rooftop venues to secretive speakeasies promising unforgettable evenings, gives guests more to look forward to than just meetings!

Accessibility, inclusivity, and diversity all intersect at Chicago's core. This thriving metropolis of diverse neighborhoods embodies the perfect blend of big-city vibrancy and small-town warmth, creating an inviting atmosphere that makes everyone feel at home. Incentive attendees of all demographics will find delight – some may gravitate toward architectural marvels or soulful blues, while others immerse themselves in the epicurean food scene or coruscating nightlife.

Chicago boasts not one but two international airports with daily direct flights to 178 domestic and 67 international destinations, making it one of the most convenient locations for corporate gatherings and business events. This accessibility enhances the event experience, allowing attendees to maximize their time in the city. Considering these highlights are just scratching the surface of this destination, this blog will explore deeper why Chicago is the perfect canvas for crafting a memorable incentive experience.

The city of Chicago
Chicago Stock Image


At the core of ETHOS, we believe in harnessing the power of business as a force for good to create positive change in the communities we serve, which is why it is an essential part of our business structure to live and work in these communities every day. We're embedded in the city's fabric, and our relationships within the community serve as your guiding compass. Our unique advantage lies in our deep-rooted connections and firsthand experience with every part of your planning process. By strategically partnering with local, woman-owned, veteran, minority, and LGBTQ-owned businesses whenever feasible, we strengthen the local economy and offer you and your guests an experience that echoes our commitment to community and inclusivity. Our fully vetted and hand-selected supplier partners embody passion and reliability, and our symbiotic relationships with like-minded entities encourage our collective growth while enriching the opportunities available to all involved.

Moreover, the impact of our choices ripples beyond business, as many of our suppliers contribute a portion of their proceeds to local charities, creating a cycle of giving integral to our ethos. From the first phone call through the final invoice, you'll see our creative process bring your event to life. Every detail is thoughtfully chosen to tell a compelling story about your company, the community you are in, and the people who contributed to making your event possible. Our dedication to remaining local resonates throughout our operations because business for us is not just about transactions; it's about partnerships. By embracing the community and celebrating its talents, you'll benefit from our brand promise of Purposeful Planning™, Meaningful Results, and leave a positive and lasting impact long after the events conclude.


Chicago sets the stage for phenomenal corporate incentive meetings with a range of show-stopping 5-star properties, each with its own unique charm and sophistication. These are a few of our favorites, and they aren't just places to stay; they're luxury experiences in and of themselves.

Four Seasons Hotel Chicago offers sleek meeting spaces with unbeatable Lake Michigan and city views. The luxurious rooms and suites blend modern comfort and classic charm, ensuring a restful stay. Attendees can relax at the spa, work out at the fitness center, or savor American cuisine with a modern twist at Allium Restaurant. This is where luxury meets the heartbeat of Chicago.

Rising majestically in the heart of downtown, St. Regis Chicago stands as a shimmering symbol of opulence and sophistication in the Windy City. The tallest building in the world designed by a female architect, guests are enveloped in a world of extravagance from the moment they step inside. The hotel's culinary offerings are equally exceptional, with gourmet dining options that tantalize the palate. St. Regis Chicago is where every moment is a vibrant celebration of luxury.

Nestled along the Chicago River, The Langham, Chicago, offers a panoramic view of the city that'll leave guests breathless. Impeccable rooms and suites with cityscape vistas provide both comfort and tranquility. Top-tier meeting facilities, an award-winning Chuan Spa, and world-class dining at Travelle Kitchen + Bar make The Langham, Chicago, a hot favorite.

Positioned along the Magnificent Mile, The Peninsula Chicago is a masterpiece of timeless elegance and sophistication. This iconic hotel boasts a rooftop terrace with awe-inspiring skyline views, a perfect venue for light welcome bites and libations. Immerse guests in state-of-the-art meeting spaces and savor authentic Chinese cuisine at the acclaimed Shanghai Terrace.


Chicago doesn't just dazzle with luxury; it's a city brimming with bucket-list experiences that'll have your team talking for years to come. Let's dive into the adventure!

Where Skyscrapers Tell the Stories

Take a private charter aboard one of our world-famous architectural tour boats and cruise along the Chicago River, where skyscrapers aren't just buildings but storytellers. As guests glide past iconic structures like the Willis Tower and the Wrigley Building, they'll discover the city's architectural history like never before. Add one of the city's 26 Michelin-starred chefs, a professional docent, and thoughtfully appointed décor, and it's sure to be an evening filled with education, entertainment, and celebration!

Culinary Explorations

Chicago's cultural scene is an enchanting tapestry of art, music, and history. Treat your guests to a night at the Chicago Symphony Orchestra or set a 200-seat Kings Table among the treasure trove of exhibitions at the Art Institute of Chicago. Chicago offers many offsite experiences that will entertain and ignite creativity and inspiration. Chicago's culinary scene is a gastronomic paradise, boasting a dynamic and diverse landscape that caters to a wide range of tastes and preferences, with more than 7,3000 restaurants and 40 James Beard award winners.

The city's culinary diversity is a standout feature, with many international cuisines in various neighborhoods. Chicago-style deep-dish pizza and hot dogs are iconic local favorites visitors must try, making foodie tours and dine-around an excellent way for groups to explore together or on their own.

Chicago's craft beer and distillery scene has seen remarkable growth, with numerous breweries and taprooms offering a wide selection of brews and styles that can't be found anywhere else in the world. Food markets like the Chicago French Market and Time Out Market provide a convenient way to sample gourmet foods and artisanal products while serving as super unique venues for corporate events.

Cultural Immersions

Chicago boasts a remarkable number of museums that serve as both repositories of knowledge and exceptional event venues – 74 and counting! From the breathtaking natural history displayed at the Field Museum to the enchanting stargazing adventures at the Adler Planetarium and the captivating sea life at Shedd Aquarium, the museum campus is a playground of historical, scientific, and artistic wonders. However, this is merely the tip of the iceberg regarding the city's cultural offerings.

Diving deeper, Chicago comprises 77 distinct neighborhoods, each offering a unique identity. Outside the Central Business District lies a world of hidden gems, allowing one to experience the authentic heart of the city's diverse communities. These smaller enclaves offer a chance to delve into various cultural experiences, whether it's savoring the flavors of Greektown, taking in the storied traditions of Chinatown, or feeling transported directly to Rome in Little Italy. In Chicago, one can travel the world without leaving the city limits, exploring the essence of different backgrounds contributing to the city's rich tapestry.

Unexpected Outdoor Adventures

Chicago offers a surprising array of outdoor adventures amidst its urban setting. Along Lake Michigan, the Lakefront Trail stretches for 18 miles, inviting walkers, joggers, bikers, and rollerbladers to enjoy stunning lakefront views. The city's sandy beaches, like North Avenue Beach, are perfect for sunbathing, swimming, and team building during summer.

Chicago's numerous parks, such as Grant Park and Millennium Park, provide green spaces for intimate picnics and large-scale outdoor events, while the expanding network of bike lanes and trails caters to those with a passion for cycling. The Chicago River and Lake Michigan offer kayaking and canoeing opportunities, and Montrose Point Bird Sanctuary attracts birdwatchers. Golf courses are plentiful, as are nearby state parks. During winter, attendees can ice skate in Millennium Park or enjoy cross-country skiing in forest preserves. Chicago's outdoor adventures, though unexpected in an urban setting, offer a refreshing connection with nature and a range of activities for every guest.

A Sports + Entertainment Scene Second to None

Chicago's entertainment scene is a melting pot of genres and cultures, deeply rooted in the city's musical heritage and encompassing a broad spectrum of styles.

Blues, often considered the city's heartbeat, has a storied history with legendary artists like Muddy Waters and Buddy Guy. The electric blues originated here, and venues like Buddy Guy's Legends keep the tradition alive.

Jazz, with luminaries such as Louis Armstrong, has a rich history in Chicago, epitomized by the iconic Green Mill Cocktail Lounge. Thanks to pioneers like Frankie Knuckles, the city also gave rise to house music, shaping electronic dance music worldwide.

Chicago's hip-hop scene gained international recognition with artists like Common and Chance the Rapper, known for their distinct styles and lyrical prowess. Both are available for keynotes and private concerts.

The city's diversity fosters a flourishing world music scene influenced by Latin, African, and Middle Eastern sounds. Moreover, Chicago hosts many music festivals, including Lollapalooza and Pitchfork, attracting global talent and passionate music enthusiasts while inspiring some whimsical event designs.

In essence, Chicago's music scene is a testament to its cultural richness, celebrating many genres and fostering innovation, making it a prominent hub in the global music landscape.

Laughter is the universal language of bonding. Chicago is renowned for its comedy clubs, with The Second City leading the pack. Plan a comedy night, and let your team roll with laughter as they connect over humor.

In addition to music and comedy, Chicago's iconic sports culture is integral to the Second City experience. It features professional teams in most major leagues, including MLB's Chicago Cubs and Chicago White Sox, the NFL's Chicago Bears, the NBA's iconic Chicago Bulls, the WNBA's Chicago Sky, and the NHL's successful Chicago Blackhawks. Each team has a dedicated fan base, with memorable championship victories contributing to their storied histories. We extend an exciting opportunity to dive headfirst into these experiences, whether it's the privilege of renting a suite at an NBA game or the thrill of stepping onto the hallowed grounds of Wrigley Field for a unique dinner set right in the ballpark. Sports play a crucial role in fostering community spirit and pride, making Chicago a haven for sports enthusiasts and a place where the love of the game is deeply ingrained in its identity.


Chicago exudes a spirit and energy that's truly electric. The city's residents, known for their Midwestern warmth and friendliness, create a welcoming atmosphere that envelops every visitor. Chicago's "can-do" attitude and rich history of innovation resonate with many businesses and can serve as an inspiration to your attendees.

The Windy City takes pride in its heritage, which often inspires visitors, creating a positive and motivational backdrop for your corporate incentive meeting. Chicago isn't just a destination; it's an experience waiting to happen. It's where luxury meets adventure, where business meets excitement. With 5-star hotels that redefine luxury and a bucket list of experiences that ignite inspiration, Chicago is the canvas upon which your corporate incentive meeting will be painted. Choose Chicago, and you're not just selecting a location; you're curating memories your attendees will surely cherish.


Get ready to meet the team that brings Chicago to life like no other! This certified woman-owned small business comprises a group of individuals who are not just event professionals but local insiders who love calling this city home. With decades of collective expertise under their belts, they're your seasoned guides who understand the city's pulse and have nurtured relationships that grant clients access to the best venues and hidden gems.

Committed to authenticity and genuine collaboration, this close-knit team thrives on synergy, ensuring they serve you well while always supporting one another. Their honest approach means you're partnering with a team that will be as transparent as they are enthusiastic. Instead of selling dreams, they're here to craft exceptional, authentic experiences that resonate with your vision. In a big city that still feels small due to our connections, you'll be embracing an authentic Chicago experience. Our diverse and inclusive team shatters stereotypes and introduces guests to a city with more than just deep dish and hot dogs.

Here is the DMC team working behind the scenes for you!


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