🌍 Market

Chicago

10 stories · First covered Feb 18, 2026 · Latest Apr 26

Chicago is a major North American hotel market and a key focus area for hospitality industry analysis. As a primary commercial and leisure destination, the market serves as a barometer for broader trends affecting hotel operations, technology adoption, and capital investment decisions across the sector.

The market has been referenced in recent industry discussions spanning operational strategy, revenue management technology, and capital allocation patterns. Chicago's significance to the hotel industry extends to policy considerations, including visitor levies and taxation structures that impact operating margins and investment returns. The market's performance and strategic developments inform broader conversations about adaptive reuse projects, staffing challenges, and the practical implementation of technology solutions in hotel operations.

Chicago Coverage
Pebblebrook Beat on FFO and Still Lost Money. That's the Whole Story.

Pebblebrook Beat on FFO and Still Lost Money. That's the Whole Story.

Pebblebrook's Q3 2025 numbers show a company that outperformed estimates on FFO and RevPAR while posting a net loss north of $30 million. The "beat" headlines miss what the owner's actual return looks like after debt service, cap-ex, and a $0.01 quarterly dividend.

Pebblebrook Lost $62M Last Year and Calls It Confidence. Let's Check the Math.

Pebblebrook Lost $62M Last Year and Calls It Confidence. Let's Check the Math.

Pebblebrook's Q4 beat and San Francisco recovery make for a great earnings narrative, but when you peel back the full-year net loss, the impairment charges, and a 2026 outlook that still might land in the red, "confident" starts to look like a very specific word choice for a very specific audience.

Your Fly-In Guests Are Disappearing. Here's What to Do Before Q2 Hits.

Your Fly-In Guests Are Disappearing. Here's What to Do Before Q2 Hits.

A 33% collapse in global air traffic and nearly 6% domestic decline aren't just airline problems. They're hotel problems. And if you're running a gateway city property that built its rate strategy on international inbound and business travel, the phone calls from your owners are about to get uncomfortable.

Marriott's Google AI Booking Deal Isn't About AI. It's About Owning the Funnel.

Marriott's Google AI Booking Deal Isn't About AI. It's About Owning the Funnel.

Marriott and Google want you excited about AI-powered direct booking. The real story is who controls the guest relationship — and who just lost leverage.

Why UK Tourism Taxes Will Backfire Spectacularly

Why UK Tourism Taxes Will Backfire Spectacularly

Hospitality leaders are begging the Chancellor to scrap visitor levies. They're fighting the wrong battle — and about to lose the war.

AI Won't Replace Your Front Desk—It'll Just Make It Obvious You Hired the Wrong People

AI Won't Replace Your Front Desk—It'll Just Make It Obvious You Hired the Wrong People

Hotels are about to spend millions on AI that can chat in 47 languages and predict guest preferences. The uncomfortable truth? It's going to expose every mediocre employee you've been making excuses for.

Austin's Newest Boutique Hotel Just Hired a Chef Before They Perfected the Pillows

Austin's Newest Boutique Hotel Just Hired a Chef Before They Perfected the Pillows

Hotel Viata brought Gerard Kenny on as executive chef while most independents are still figuring out whether to do grab-and-go or partner with Uber Eats. That's either brilliant or reckless.

Allianz Buys 400K Shares of RLJ — Here's What Institutional Money Sees

Allianz Buys 400K Shares of RLJ — Here's What Institutional Money Sees

When a European institutional investor drops millions into a struggling U.S. hotel REIT, they're not being charitable. Allianz Asset Management just took a 401,189-share position in RLJ Lodging Trust, and the timing tells you everything.

Adaptive Reuse Looks Sexy Until You See the Pro Forma

Adaptive Reuse Looks Sexy Until You See the Pro Forma

Two historic prisons — one in Nara, one in Istanbul — are becoming luxury hotels. The headlines write themselves, but the operating economics tell a different story.

Tech Won't Save Your Hotel in 2026 — Operations Will

Tech Won't Save Your Hotel in 2026 — Operations Will

Another year, another wave of headlines promising that technology will transform hospitality. I've heard this story for two decades, and the properties that win still get the fundamentals right first.