Chicago Debrief

Architecture, Deep-Dish, and a City That Keeps Proving Its Critics Wrong

Why Visit Now

Chicago is having a moment — and the numbers back it up. The city welcomed approximately 55.3 million visitors in 2024, generating nearly $21 billion in economic impact, and 2026 is tracking even stronger. Condé Nast Traveler readers voted Chicago the Best Big City in the U.S. for an unprecedented ninth consecutive year, and travel booking data confirms it: Chicago is surging as a domestic destination in 2026, drawing strong numbers from leisure travelers who are rediscovering one of America's most underrated urban experiences.

The city is firing on all cylinders right now. The culinary scene — always formidable — continues to evolve with a new wave of chef-driven restaurants joining the city's remarkable roster of Michelin-starred dining. The Riverwalk and lakefront are fully transformed into world-class public spaces. The architecture boat tours are as popular as ever, and summer in Chicago, with its outdoor festivals, rooftop bars, and the electric energy of the lakefront, is one of the great domestic travel experiences available to American travelers.

One thing first-time visitors often don't expect: Chicago is extraordinarily walkable and well-organized. The Loop, the Magnificent Mile, River North, the Gold Coast, and the Museum Campus are all tightly connected, and the L train handles everything else. It's a city that reveals itself quickly and rewards every hour you spend in it.

Where to Stay

Chicago's hotel scene has something for every traveler, with a concentration of excellent properties in the River North, Magnificent Mile, and Loop neighborhoods:

  • Ultra-Luxury: The St. Regis Chicago (formerly Vista Tower) is the city's newest and most architecturally striking skyscraper hotel, with sweeping Lake Michigan and city views, a world-class spa, and the signature St. Regis butler service. The Peninsula Chicago on the Magnificent Mile remains the gold standard for refined luxury, consistently ranking among the top hotels in the entire country. Four Seasons Chicago, steps from the Magnificent Mile and Water Tower Place, is the perennial choice for discerning travelers.
  • Boutique Luxury: The Langham Chicago, situated in the landmark Wrigley Building along the Chicago River, delivers intimate luxury with stunning river views and one of the city's best spas. Time Out calls it the ideal choice for a "luxe-yet-lowkey weekend" with easy access to Millennium Park and the Art Institute. The new L7 Chicago by Lotte brings a sophisticated South Korean hospitality sensibility to a restored 1912 Riverwalk high-rise, with a standout Korean American steakhouse, PERILLA, and a rooftop bar — one of the most interesting new hotel concepts in the city.
  • Mid-Range: Hotel Zachary, directly across from Wrigley Field in Wrigleyville, is the choice for travelers who want neighborhood character over downtown convenience — it's a genuinely fun Chicago experience. The Kimpton Gray Hotel in the Loop occupies a beautifully restored 1914 beaux-arts building and delivers boutique style at competitive prices.

Timing note: Chicago summers (June through August) are spectacular and very popular — book well in advance. September and October are arguably the sweet spot: weather is still excellent, crowds thin, and hotel rates soften. The city's winter has a charm of its own, but it's not for the faint of heart.

Getting There

Chicago is one of the best-connected cities in the United States, served by two major airports:

  • O'Hare International Airport (ORD): One of the world's busiest airports and the primary hub for American and United Airlines, with nonstop service from virtually every U.S. city and dozens of international destinations. From Florida, nonstop flights from Orlando, Tampa, Miami, and Fort Lauderdale are available on multiple carriers, typically running under three hours. The Blue Line CTA train connects O'Hare to downtown Chicago in about 45 minutes for a few dollars — fast, reliable, and no traffic.
  • Midway Airport (MDW): Chicago's secondary airport, closer to the city's south side and a major hub for Southwest Airlines. Midway is smaller, easier to navigate, and often offers more competitive fares for travelers flying Southwest. The Orange Line CTA train connects Midway to the Loop in about 30 minutes.

Once downtown, Chicago's grid system and the L train make getting around genuinely easy. Rideshare is widely available, and the city's flat, well-maintained sidewalks make it one of the most pleasant walking cities in the country during spring, summer, and fall. A rental car is not needed and would be more hindrance than help in the city center.

A Word From Your Travel Advisor

"Chicago is the city I recommend most often to travelers who think they want to go to New York but aren't sure they're ready for the pace and the price tag. It has everything — world-class food, incredible architecture, great museums, beautiful lakefront, fantastic hotels — at a meaningfully more accessible cost. And it tends to surprise people in the best possible way."

As your Jaunt Around advisor, I can help you pick the right neighborhood and hotel for your travel style, time your visit to take advantage of Chicago's best seasons, and build an itinerary that goes deeper than the Bean and Giordano's. Chicago has so much more to offer than the tourist checklist — and that's exactly the kind of trip I love helping people plan.

Ready to book your Chicago getaway? Let's talk.