Sitting 103 floors above the street at dawn, Don Welsh, president and CEO of Destinations International (DI), addressed a group of meetings industry media at Chicago’s Skydeck at Willis Tower ahead of the organization’s Annual Convention July 9-11.
“These are interesting, dynamic times,” he said, not stepping around the fact that the geopolitical atmosphere has the travel industry on edge. But, he hinted that Chicago might be one of the best places to tackle the challenging issues of the moment.
“Chicago works a little harder than most because the people of Chicago work a little harder than most,” Welsh said.
As president and CEO of Choose Chicago from 2011-2016, he knows from experience the energy Chicago can bring to meetings and conventions. The DMO’s new leader, Kristen Reynolds, who took the helm in May, echoed the sentiment, noting that major events like the National Restaurant Association Show and NASCAR Chicago Street Race had summer visitation numbers off to a great start.
In the travel industry, some of the brightest minds convened in Chicago during what is shaping up to be a tumultuous, uncertain time for inbound travel to the U.S. Following our fam with Choose Chicago, DI’s Annual Convention broke attendance records, bringing more than 2,000 attendees from 27 countries to McCormick Place. A few weeks prior, Chicago hosted IPW, U.S. Travel Association’s premier travel tradeshow for driving international visitation to the states. That event attracted more than 5,000 attendees from more than 60 countries.
Perhaps conventions continue to pick Chicago because it is an ideal setting for problem solving and innovating in times of change. The city is known for its grit, determination and defying expectations. In its 188-year history, Chicago has literally risen from the ashes (one-third of the city burned to the ground in the 1871 Great Chicago Fire) and rebuilt itself in time to host the 1893 World’s Fair. In an incredible feat of engineering, it reversed the flow of the Chicago River in 1900 to empty into the Mississippi River instead of Lake Michigan. The iconic Willis Tower (formerly Sears Tower) was the tallest building in the world for nearly 25 years—and that just scrapes the surface.
The work never stops. Chicago continues to prove itself as a master of innovation and determination, and therefore a meetings powerhouse. One only has to spend some time there to see it and feel it.
Unique Venues & Experiences in Chicago
Breakfast at the Skydeck was certainly an awe-inspiring way to kick off the day. Randy Stancik, general manager of Skydeck, gave our group an exclusive tour of the base of Willis Tower and the Chicago Skydeck Museum, bursting with 30,000 square feet of exhibit space that details the fascinating history of Chicago. Opened in 2021, it’s the most immersive way you’ll ever wait in line for an attraction.
We shot up to the 103rd floor and enjoyed the space before it was open to the public. I both stood where Ferris Bueller and his friends stood during 1986’s Ferris Bueller’s Day Off and nervously scooted back to take a picture on The Ledge, the glass viewing platform that opened in 2009 and extends more than four feet out and over Wacker Drive and the Chicago River. The Skydeck can be used for private events, as can the 99th floor event space, which offers the same 360-degree views of Chicago and is popular for corporate events. It can seat 175 or host up to 300 standing.
The Willis Tower itself is a marvel of engineering and architecture. Chicago is full of pioneering architectural feats, and one of the best ways to learn about the city’s prowess in the field is aboard an iconic First Lady architecture cruise. Departing from the Riverwalk, volunteer docents—who go through meticulous training with the Chicago Architecture Center—enthusiastically dictate Chicago’s past, present and future via the stories of its buildings during a 90-minute cruise. First Lady has a variety of vessels that can host private events, too, for groups as large as 250.
We stood atop its tallest building and cruised along the famed river. So, it was only fitting that next, we explored Chicago from the sky.
Meeting at the hangar at Vertiport Chicago, we embarked on a thrilling helicopter tour, cruising above Lake Michigan’s shoreline, passing landmarks such as Soldier Field and Chicago’s Museum Campus, and observing the city’s incredible design from a different vantage point.
The tour is certainly a breathtaking add-on to any event, but the hangar itself can host events, too. Clients as large as Lollapalooza and Live Nation have chosen the spot for their pre-parties. Vertiport Chicago has 9,000 square feet of indoor space and 14,000 square feet outdoors. Privately owned and located on a 10-acre site that includes a five-acre tarmac, additional space can be used for guest parking or to extend the event footprint.
Revenue from events also directly supports Vertiport Chicago’s emergency medical services operations in the Midwest, with a primary focus to facilitate organ and patient transfers at no cost. Launched in April 2015, it is one of North America’s largest and Chicago’s only vertical helicopter landing facility.
[Related: More meeting and event news in Illinois]
New and Renovated Hotels in Chicago
Chicago is home to the world headquarters of Hyatt Hotels, so it made sense that our home base was the Hyatt Regency Chicago. The AAA Four Diamond hotel is home to 2,032 guest rooms and suites and 240,000 square feet of meeting and event space. The hotel celebrated its 50th anniversary last year and marked the milestone with a $150 million renovation of all the guest rooms and Regency and Crystal Ballrooms. This December, the hotel plans to continue renovating other meeting spaces in the hotel, updating the Grand Ballroom, Grand Hall and East Tower Concourse meeting rooms, completed by January 2026.
The hotel is a master of meetings and conventions. According to the property’s sales and marketing teams, on average, 65% of the Hyatt Regency Chicago’s business comes from group/conventions.
Down the river from the Hyatt is The St. Regis Chicago, which opened in 2023 and is one of the most exciting luxury entrants to the Chicago hotel scene in recent years. The hotel resides in the third-tallest building in Chicago, taking up the first 11 floors, with an imaginative design by a local woman architect, Jeanne Gang.
Upon entering, our group was welcomed with the brand’s signature evening ritual, the champagne sabrage. Inspired by Napoleon Bonaparte, who famously opened champagne with his saber in both victory and defeat ("In victory, you deserve champagne; in defeat, you need it"), a hotel butler demonstrated the art of sabrage, an experience that can be brought into private events on the property.
Following, we toured the 11,000-plus square feet of meeting space at The St. Regis Chicago, which exudes elegance. The largest space is the 4,721-square-foot Astor Ballroom, right off the lobby, while the remaining space resides on the third floor. Other highlights include The St. Regis Terrace and two signature restaurants—Tuscan cuisine from Tre Dita and Japanese-inspired dishes from Miru—which can both be bought out for exclusive group use.
Smaller groups should take note of L7 Chicago by LOTTE, another stop on our Chicago hotel tour. Opened in June 2024 following a refresh and rebrand from the Kimpton Hotel Monaco Chicago, it’s the first L7 to open in the U.S. The South Korean lifestyle brand chose the Loop neighborhood—Chicago’s central business district—as its home, featuring 191 guest rooms and suites. The property has more than 4,000 square feet of meeting space and is best for groups of up to 80, offering exclusivity and privacy in the heart of downtown.
Rounding out our hotel visits, Thompson Chicago gave us a glimpse into Chicago’s posh Gold Coast neighborhood. Stevie Nicks, Billy Joel, Lady Gaga and Prince have all been said to have frequented the property. With 247 rooms, the hotel has a boutique feel and is steps from trendy shops and restaurants. We dined at adjoining Tavern on Rush, an upscale steakhouse that has been a staple of the Gold Coast neighborhood for 25 years. Its new home at Thompson Chicago adds a variety of private dining spaces for groups. Additionally, the hotel plans to embark on a refresh of its 6,000 square feet of meeting space this September.
[Related: The Latest New and Renovated Hotels and Venues]
On the Horizon: Obama Presidential Center
One of the final stops during our visit was a perimeter tour of the highly anticipated Obama Presidential Center. Set on 19 acres in Jackson Park in the Hyde Park neighborhood on Chicago’s South Side, the development is scheduled to wrap in spring 2026 and open as “a lively community hub, economic anchor and beacon of democracy.”
The centerpiece of the development is the museum, a 16-story structure with a design reflecting the idea of ascension and upward movement starting from a grassroots level, reflective of President Barack Obama’s 2008 campaign and presidential win. The museum will be the only ticketed area on campus and will house four floors of exhibits. Groups can arrange private tours of the galleries. Other spaces within the museum will be available for private events, including the Sky Room and Sky Room Vista on the eighth floor. Other spaces on campus that can be used for events will include the Forum Building, outdoor lawns and gardens, and the 45,000-square-foot athletic center Home Court.
Something for Everyone
I grew up in the suburbs outside of Chicago, visiting the city frequently throughout my life, and I still learned many new things about it on this trip. And the same can hold true for you, even if you’ve brought your event to the city before. Its ever-evolving nature is part of the allure. Mark Twain may have said it best:
“It is hopeless for the occasional visitor to try to keep up with Chicago—she outgrows his prophecies faster than he can make them. She is always a novelty; for she is never the Chicago you saw when you passed through the last time.”
Connection
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