7 More Chicago Experiences That Are Worth Every Penny (Even If You’re Watching the Budget)
Chicago doesn’t need another list of “things to do.” Everyone already knows about The Bean, the Mag Mile, and the coffee shops on every corner. Those are fine for tourists or a first trip here. But when you’re the one hosting? The basics won’t cut it. You need experiences that feel like secrets. The kind of moments that make people say, “I’ll never forget that.”
That’s what I love most about living here: Chicago always finds a way to surprise you. And when you choose the right experiences, an ordinary night turns into something elevated, curated, and truly unforgettable.
In my last LinkedIn post, I shared 3 of my favorite “worth it” Chicago splurges (and I’ll list them below). This time, I’m giving you 7 more — plus clever ways to make them work even if you’re watching the budget. Because sometimes you do go all-in on the Michelin star moment… and sometimes the smarter move is a creative twist that still wows.
Here’s a quick recap of the first 3 I shared:
Alinea Chef’s Table — A once in a lifetime Michelin star performance. The hospitality, the showmanship, the food.. it’s otherworldly.
After Hours at the Art Institute — Sip champagne with a private curator who walks you through the museum with zero crowds.
Vanille Patisserie Class — Interactive elegance with French pastry chefs thats harder to book than a parking spot on Michigan ave.
But that’s just the beginning. Chicago has so many more unforgettable experiences. Some are splurges. Others can be pulled off without overspending. All of them signal thoughtfulness, creativity, and you matter.
So without further ado, here are 7 more Chicago experiences that are worth every penny.
1. Private Architectural Boat Cruise
There’s a reason Chicago’s architecture cruises are famous — the city is basically an outdoor design museum. But instead of cramming into a crowded boat, imagine hosting your own group on a private yacht with an expert guide narrating the skyline’s stories. Cocktails in hand, sunset reflecting off the glass towers, clients leaning in to hear the history of Frank Lloyd Wright, Mies van der Rohe, and Jeanne Gang’s Aqua Tower. It takes a “must do” attraction and transforms it into a curated experience.
💡 Budget tip: Shoulder seasons (spring/fall) often come with lower charter rates. Or look for smaller semi private luxury charters that feel private without the full yacht price tag.
2. Big Delicious Planet Urban Farm Dinner
Tucked in the middle of the West Loop is a four acre organic farm most people don’t even know exists. Big Delicious Planet is both a certified green catering company and an urban oasis. Their long-table dinners are straight out of a magazine: twinkle lights strung overhead, fresh herbs perfuming the air, vegetables picked just feet from the table, and courses that shift with the season. Guests leave feeling like they stumbled into a secret garden party in the middle of the city. It’s unexpected, stylish, and incredibly memorable.
💡 Budget tip: Instead of hosting a private buyout (which runs into the thousands), purchase tickets to their public farm dinners. You’ll get the same magical vibe, chef led menu, and setting, but at a fraction of the cost.
3. Helicopter Ride Over Chicago
Some memories take only 20 minutes to make and people, this is one of them. Chicago’s skyline is already iconic, but seeing it from a helicopter is next level. You sweep over Millennium Park, Navy Pier, Soldier Field, and the blue curve of Lake Michigan, with the city glittering beneath you. At night, it feels cinematic. By day, it’s crisp and breathtaking. This is one of those “bucket-list” splurges that clients will still be talking about when they’re back home in the office.
💡 Budget tip: Evening charters are the most expensive. Daytime or early evening group flights (shared with a small number of other passengers) are significantly more affordable.
4. Esmé
My personal favorite next to Alinea. Dining at Esmé is not just about the food it’s about purpose. This Michelin starred Lincoln Park restaurant creates menus in collaboration with local artists and ties each season’s tasting menu to a philanthropic cause. That means your meal might support a community arts program, showcase the work of a local painter, or contribute to a social initiative. The food itself is exquisite: colorful, inventive plates that look like art pieces but deliver serious flavor. It’s dinner as storytelling— thoughtful, beautiful, and deeply Chicago.
💡 Budget tip: Can’t commit to the full tasting menu? Keep an eye on Esmé’s special prix fixe events or artist collabs. These still deliver the artistry and intention, often at a lower price point and usually 1-2 times per month.
5. Oriole Kitchen Table
Hidden in an unmarked West Loop building, Oriole is one of Chicago’s crown jewels: two Michelin stars, 12+ course tasting menus, and hospitality that’s famously warm. The Kitchen Table experience is the insider’s move as you’re seated inside the kitchen, just steps from the pass, watching the chefs meticulously plate every course. It feels secret and illegal in the best way possible! I love it so much that I’ve done this multiple times and they always outdo themselves!
💡 Budget tip: Can’t snag the Kitchen Table? A standard reservation in Oriole’s dining room is still amazing. The same chefs, the same tasting menu, at a slightly gentler price point. You can also sit at the bar on select nights for 60/person which is about 1/8 of how much it normally costs!
6. The Green Mill Jazz Lounge
Few places in Chicago drip with as much history as the Green Mill. This Uptown landmark was Al Capone’s favorite hangout and hasn’t lost its 1920s speakeasy swagger. Booths still hold whispers of mobsters and the jazz? Surprisingly great! Bringing clients here feels like stepping into another era.
💡 Budget tip: Cover charge is usually under $20. Arrive early to snag prime seating and you’ve just delivered a legendary Chicago night at an unbeatable cost.
7. Private Suite at the Lyric Opera or Symphony Center
For founders and top clients, sometimes the real wow factor isn’t about flash it’s about access. Imagine an evening in a private box at the Lyric Opera or Symphony Center, where velvet seats, crystal chandeliers, and world-class performances set the tone. Instead of waiting in lines or jostling with the crowd, your guests are ushered into an exclusive suite with in suite catering, white glove service, and wines hand selected by a sommelier.
💡 Budget tip: Full box buyouts can be pricey, but many performances offer smaller VIP packages or shared suite experiences that still deliver exclusivity at a gentler cost.
Final Thoughts
Chicago has a million things to do, but only a handful that make people stop and say, “That was worth it.” The right experience doesn’t just fill an evening, it shows your clients you thought of everything. Whether it’s a once in a lifetime Michelin-star tasting, a garden dinner tucked away in the city, or live jazz in Capone’s old haunt, these are the kinds of moments that turn trips into stories.
👉 Want the full list of 10 Chicago experiences that actually justify the price tag? Check out my LinkedIn post here.
