Chicago for the 2026 Presidents Cup: A Host’s Guide to Golf’s Biggest Week in the Windy City
Curated By
Journeys with JB
Curator’s statement
I live in Chicago, and I can tell you this city knows how to show up for a big event. In September 2026, the Presidents Cup comes to Medinah Country Club for the first time ever, bringing the best American and International players to a course that has already hosted the Ryder Cup, three U.S. Opens, and two PGA Championships. For companies hosting clients, this is the rare event that pairs world-class golf with a truly world-class city just 45 minutes away, where Michelin-starred dinners, private river cruises, and five-star suites turn a tournament week into a relationship-building week. As a Chicago-based advisor, I plan these weeks end to end, from hotel blocks and ground transfers to the dinners and experiences that happen after the final putt drops.
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Things to do in Chicago
Cruise views | Photo captured by Jea B.
Watch the matches at Medinah Country Club
The tournament runs September 22–27, with practice rounds early in the week and match play Thursday through Sunday. Premium hospitality venues like the Captains' Club put your group above the action with elevated food and beverage, ideal for hosting clients who expect more than a grandstand seat.
Charter a private architecture cruise on the Chicago River
Chicago's architecture river cruise is the single best introduction to the city, and a private charter turns it into a floating cocktail reception for your group. It is my go-to recommendation for a welcome event the evening clients arrive.
Book an after-hours or docent-led private tour at the Art Institute of Chicago
One of the finest art museums in the world, home to American Gothic and an unmatched Impressionist collection. A private guided hour before dinner is a sophisticated touch for clients who are not golf-obsessed.
Take in the skyline from 360 CHICAGO or the Signature Room level of the former Hancock Center
The view stretches across Lake Michigan and four states on a clear day. Time it for sunset and pair it with a champagne toast for an easy, high-impact group moment.
Reserve a rooftop evening at a hotel bar like Cindy's or LH Rooftop
Late September in Chicago is genuinely beautiful, with often warm days and crisp evenings, and the rooftops overlooking Millennium Park are at their best. It is the perfect casual close to a tournament day.
Walk Millennium Park and the Lakefront Trail
Cloud Gate (the Bean), Crown Fountain, and the Lurie Garden are all free and walkable from the Loop hotels. Build in unstructured morning time here so clients can move at their own pace before heading to Medinah.
Play a round at a Chicago-area championship course
For groups arriving early, courses like Cog Hill's Dubsdread or The Glen Club let your guests test their own games before watching the pros. I can arrange tee times and transportation as part of the week's itinerary.
Tour Wrigley Field or catch the energy of Wrigleyville
Even in the offseason conversation, Wrigley Field is hallowed ground, and the behind-the-scenes tour is a hit with sports-minded clients. If the Cubs are in a playoff push that week, even better.
Places to eat & drink in Chicago
Alinea (Lincoln Park)
Chicago's three-Michelin-star icon and one of the most creative dining experiences in the world. Book the Kitchen Table or a private room months ahead for a client dinner nobody will forget.
Smyth (West Loop)
A three-Michelin-star tasting menu that feels warm and personal rather than formal. This is my pick for smaller groups of four to six who appreciate food at the highest level.
Gibsons Italia (River North)
Steakhouse power dining with floor-to-ceiling views of the river and a private dining program built for corporate hosting. The service team here understands client dinners better than almost anyone in the city.
Bavette's Bar & Boeuf (River North)
A moody, candlelit steakhouse that feels like a 1920s supper club. The back room is one of the best private dining spaces in Chicago for groups who want atmosphere with their ribeye.
Monteverde (West Loop)
Chef Sarah Grueneberg's handmade pastas draw lines for a reason. It is a great choice for a more relaxed group dinner that still delivers a memorable meal.
RPM Seafood (River North)
Polished, scene-y, and sitting right on the river with floor-to-ceiling glass. Strong private dining options and a raw bar that makes a great first impression.
The Aviary (West Loop)
Cocktails treated with the same precision as a tasting menu, from the Alinea Group team. Reserve the Kitchen Table experience for a small-group nightcap that doubles as theater.
Lou Malnati's or Pequod's for deep dish
Sometimes the most memorable client moment is the least formal one. A casual deep-dish lunch is a Chicago rite of passage and a fun counterweight to a week of fine dining.
Need to know
Book early, and I mean now. Tournament week will compress hotel inventory across downtown Chicago and the western suburbs, and the best hospitality packages and private dining rooms are claimed many months out.
Medinah is about 25 miles west of downtown, roughly 45 minutes by car, so plan dedicated ground transportation for your group rather than relying on rideshares on competition days. Most corporate groups do best staying downtown for the dining, energy, and walkability, then shuttling to Medinah each morning.
Late September weather in Chicago typically means highs in the 60s and 70s, with cool evenings, so advise guests to pack layers.
O'Hare is the closest major airport to both downtown and Medinah, with Midway as a solid alternative.
And if you are hosting international clients, note that the International Team's presence makes this a uniquely global event, which is a great hook for entertaining overseas partners.
I handle the full week for corporate hosts: room blocks, hospitality coordination, private experiences, and all the logistics in between.
Travel Advisor
Journeys with JB
Jea Breshears
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