While New York City attracts approximately 64 million visitors annually with its iconic skyline and cultural attractions, there's a compelling case for choosing Chicago as your next American city break. According to US Travel Editor Ted Thornhill, the Windy City offers all of New York's swagger with significantly less stress and expense.
Architectural Marvels and Sky-High Thrills
Chicago holds the distinguished title of skyscraper birthplace, with the 138-foot Home Insurance Building completed in 1885 marking the beginning of the high-rise era. The city's spectacular skyline features over 100 skyscrapers, including the magnificent 1,451-foot Willis Tower, where visitors can experience the nerve-testing Ledge - a glass box extending 4.3 feet over the street below from the 103rd floor.
Another architectural highlight includes 875 North Michigan Avenue (formerly John Hancock Center), where the Tilt experience leans visitors out over the sidewalk at a 30-degree angle. For comprehensive architectural appreciation, the Architecture River Cruise provides a narrated tour of Chicago's iconic buildings from the water, an experience New York simply cannot replicate.
Pristine Beaches and Urban Oases
Unlike New York where beaches require at least 45 minutes of subway travel from Manhattan, Chicago's 24 public beaches sit mere steps from downtown along 26 miles of Lake Michigan shoreline. The Chicago Park District maintains these sandy stretches with lifeguard patrols and activities including volleyball and DJ sets.
The 18-mile Lakefront Trail connects each beach, allowing seamless beach-hopping with breathtaking skyline views. The freshwater lake eliminates saltwater irritation and jellyfish concerns, making Chicago's urban beaches significantly more enjoyable than their New York counterparts.
Cultural Convenience and World-Class Museums
Chicago's cultural institutions cluster conveniently together, unlike New York's often miles-apart attractions. The Art Institute of Chicago, founded in 1879, houses over 300,000 works including Monet's Water Lilies and Van Gogh's The Bedroom alongside pieces by Warhol, Picasso and Dalí.
A mere 25-minute stroll south reveals the Museum Campus, where three world-renowned institutions sit side-by-side: the Field Museum featuring Sue, the most complete T-rex ever discovered; the Adler Planetarium with spectacular sky shows; and the Shedd Aquarium displaying over 30,000 creatures in five million gallons of water.
Culinary Excellence and Legendary Specialities
Chicago's deep-dish pizza represents an entirely different culinary experience from New York's thin-crust offerings. These pie-like creations feature buttery crusts encasing layers of gooey cheese and chunky tomato sauce, with establishments like Lou Malnati's, Giordano's and Pequod's Pizza serving gold-standard examples.
The Chicago hot dog follows strict assembly rules: an all-beef frankfurter in a steamed poppy seed bun with yellow mustard, bright green relish, chopped onions, tomato wedges, dill pickle spear, sport peppers and celery salt - notably excluding ketchup. Top spots include Portillo's, The Wieners Circle and Superdawg Drive-In.
For fine dining enthusiasts, Chicago matches New York's culinary heights with two three-Michelin-starred restaurants - Alinea and Smyth - plus several one and two-star establishments including Oriole, Ever and Kasama.
Transport as Attraction and Urban Exploration
Chicago's elevated L train system serves dual purposes as both transportation and architectural tour, passing remarkably close to buildings at stations like Harold Washington Library–State/Van Buren and Merchandise Mart. Key attractions accessible via L train include Chinatown from Cermak-Chinatown station, Clark Street's shopping from Berwyn station, and Millennium Park from Washington/Wabash station.
Relaxed Atmosphere and Welcoming Locals
Chicago offers a noticeably more relaxed pace than frantic New York, with wider sidewalks and friendlier locals possessing a Midwestern warmth. The city maintains world-class attractions without the overwhelming crowds and shoulder-barging intensity of New York streets.
Significant Cost Advantages
Chicago delivers substantial savings across all travel aspects. Luxury hotel rooms in central Chicago typically cost $200-300 per night compared to New York's $400-600 range. Dining proves considerably more affordable, with deep-dish pizza feasts costing $25-40 per person versus New York's $50-70 equivalent.
Transportation savings include L train fares at $2.50 compared to New York's $2.90 subway, and airport transfers costing $5 from O'Hare versus $8.25 from JFK. These financial advantages make Chicago an increasingly attractive alternative for budget-conscious travellers seeking world-class urban experiences.
