Chicago: The City That Built Itself Twice

A City That Earned Its Confidence

Chicago burned to the ground in 1871 and responded by essentially inventing the modern skyscraper. The architects who flooded in after the fire, constrained by a flat lakeside site with poor soil, figured out how to build upward on steel frames rather than outward on stone walls. The result was the Chicago School of Architecture, which changed cities worldwide. That confidence in large-scale ambition is still visible everywhere: in the elevated train rattling between glass towers, in the museums that are genuinely among the best in the world, in a food scene that generates Michelin stars without apparent effort. Chicago is the kind of city that tends to exceed what visitors expected.

Getting In

Chicago has two airports. O’Hare International (ORD) handles most international and long-haul traffic and is served by the Blue Line CTA elevated train, which runs 24 hours and reaches the Loop in around 45 minutes for a flat fare of $5. Midway (MDW) is closer to downtown and served by the Orange Line for $2.50, with a journey of roughly 30 minutes. Both are significantly cheaper than a rideshare, which runs $50-70 from O’Hare and $25-30 from Midway. Car rental is not recommended for Chicago itself since downtown parking typically costs $50 or more per night.

Getting Around

The ‘L’ (elevated train) network is the correct way to navigate Chicago. Eight colour-coded lines cover most of the city and operate frequently from early morning to past midnight. A single ride costs $2.50, and a day pass is available for unlimited travel. The system is old and occasionally noisy but covers the neighbourhoods that matter for most visitors. For longer journeys or late-night returns, rideshare is straightforward.

What to See

The Architecture River Cruise

This is the single best way to understand Chicago in a short time. The Chicago Architecture Center runs 90-minute guided cruises aboard the First Lady, departing from the Michigan Avenue Bridge at Wacker Drive. Tickets cost around $54-62 in 2026 depending on date and departure time, and the tours are led by trained volunteer docents who cover more than 50 buildings. The cruise runs March through November, with multiple daily departures. Book online at least three to five days ahead for summer weekends; the sunset sailings fill faster. The combination of river-level perspectives on buildings that look ordinary from street level makes this worth doing even for visitors who do not consider themselves interested in architecture.

Skydeck Chicago at Willis Tower

The observation deck on the 103rd floor of what was, briefly, the world’s tallest building still offers the clearest aerial reading of Chicago’s grid and its extraordinary lakefront setting. Adult tickets in 2026 start at $32 for standard entry, with timed-entry slots in 30-minute windows. Expedited entry starts at $55. Booking online in advance is strongly recommended because slots can sell out, and the experience of arriving without a ticket is less enjoyable than the view deserves. The Ledge, a set of glass boxes extending over the exterior wall, is included and is the kind of thing that produces interesting reactions in people who think they are fine with heights until they are standing on it.

Millennium Park

The Jay Pritzker Pavilion by Frank Gehry and Cloud Gate (the bean-shaped sculpture officially titled “Cloud Gate” but called the Bean by everyone) are in Millennium Park, which is free to enter and sits on the lake’s edge at the eastern end of the Loop. The Bean is genuinely worth the tourist crowds around it because the reflective surface creates strange, wide-angle distortions of the city skyline and the people under it. Summer evenings at the Pritzker Pavilion, which hosts the Grant Park Music Festival with free outdoor concerts, are one of Chicago’s better free experiences.

The Art Institute of Chicago

One of the most significant art museums in the United States occupies a Beaux-Arts building on Michigan Avenue with a collection that runs from ancient to contemporary. The Impressionist collection is particularly strong, with well-known works by Seurat, Monet, and Toulouse-Lautrec. Georges Seurat’s “A Sunday on La Grande Jatte” is here and is larger than most visitors expect. Adult admission is around $26 for non-Chicago residents. The Modern Wing, added in 2009 and designed by Renzo Piano, is worth seeing for the building itself.

Navy Pier and the Neighbourhoods

Navy Pier is a large lakefront entertainment complex that functions well for families with young children. For most adult visitors, the neighbourhoods are more interesting. Wicker Park and Bucktown on the Blue Line have independent restaurants and bars with less tourist overlay. Logan Square, further west on the same line, has the kind of food and bar scene that local publications have been writing about since around 2015 without it losing its energy. Pilsen, on the Pink Line, is a predominantly Mexican American neighbourhood with excellent tacos and a strong street art presence, and it is one of the more significant under-visited areas of the city.

Where to Eat

Chicago’s food scene has earned 21 Michelin-starred restaurants as of the 2026 guide. Alinea, in Lincoln Park, has held three stars for years and represents the kind of progressive multi-course experience that still draws people to Chicago specifically for dinner. It requires advance reservation and planning for the tasting menu pricing, which is substantial.

At the more accessible end of Michelin recognition, Indienne in the West Loop earned a star in 2023 as the city’s first starred Indian restaurant and remains one of the more interesting dining experiences in the city. Kasama, a Filipino restaurant in Ukrainian Village, was promoted to two Michelin stars in 2025 and operates a daytime bakery and evening tasting menu that together represent a genuinely distinctive approach.

For deep-dish pizza, which Chicago invented and which divides opinions sharply, Lou Malnati’s is the most consistent across locations, and Pequod’s in Lincoln Park makes a version with a caramelised crust edge that is the better of the two in texture. The honest assessment of deep-dish is that it is closer to a cheese-and-tomato pie than to what most of the world calls pizza, and visitors who approach it expecting the latter will enjoy it more.

Girl and the Goat in the West Loop, from Stephanie Izard, remains popular and worth the booking effort for sharing-style plates. Station, the bar scene in Logan Square, produces the kind of low-key excellent cocktail bars that the neighbourhood has built a reputation on.

Where to Stay

The River North neighbourhood offers the densest concentration of mid-range and upscale hotels within walking distance of the main Loop attractions. The Langham Chicago, on the river, occupies the upper floor of a Mies van der Rohe building and delivers a genuinely high-end experience. The Wit in the Loop has a useful rooftop bar and is positioned centrally enough that the ‘L’ stop is immediate.

For a slightly different approach, staying in Lincoln Park or Wicker Park puts you closer to the neighbourhoods that Chicago residents actually use and reduces the sense of operating entirely within the tourist loop. The price differential is often meaningful and the access to the ‘L’ remains good.

Seasonal Considerations

Chicago’s reputation for cold winters is accurate. January temperatures regularly drop below -10 Celsius, and the wind off Lake Michigan makes it feel significantly colder. The city functions throughout winter and the indoor attractions, including the museums and the architecture of the Loop itself, are excellent in cold weather. Summer is the peak season, with outdoor concerts, the lakefront beaches, and the architecture cruise operating at full frequency. Spring and autumn are the most comfortable for walking, though April in particular can be very unpredictable.

The Chicago Marathon in October draws large crowds and affects hotel prices and availability for that weekend. If you are not running it, plan around it.

One Practical Note

The architecture cruise is the highest-value single activity in Chicago on a per-hour basis. Book it first, build the rest of the trip around it, and if possible take the sunset sailing rather than a mid-afternoon departure. The light on the river at dusk, with the towers lit from inside, is the image most visitors carry away.