Chicago, USA
The Great Chicago Fire of 1871 burned for two days, destroyed nearly 18,000 buildings, and left roughly a third of the city’s population homeless. Within two decades, Chicago had rebuilt into one of the most architecturally ambitious cities in the world and invented the skyscraper. That energy - compulsive, slightly aggressive, deeply proud - is still the operating system of the place, and it makes Chicago a more interesting city to spend time in than its relative neglect on international tourist itineraries would suggest.
Getting from the Airport
O’Hare International Airport (ORD) is the main international gateway, 27 km northwest of downtown. The CTA Blue Line train is the right call: 5 USD flat fare, runs 24 hours a day, and takes 40 to 45 minutes to reach the Loop (Washington or Clark/Lake station). It runs directly from the O’Hare station inside the airport’s lower level. A taxi or rideshare (Uber, Lyft) costs 50 to 65 USD plus tip and takes 30 to 50 minutes, which can exceed the train time during peak hours; the Kennedy Expressway into downtown is one of the more reliably congested stretches of urban freeway in the US.
Midway Airport (MDW) is 16 km southwest of downtown and primarily serves domestic flights. The CTA Orange Line connects Midway to the Loop in about 30 minutes for 2.50 USD.
Getting Around
The CTA “L” train network covers all the areas visitors want to reach. The Red, Blue, Brown, Green, Orange, Pink, and Purple lines form a grid across the city that is less confusing than it looks; the Loop elevated tracks in the city centre serve as a hub for the Brown, Green, Orange, Pink, and Purple lines. A Ventra card (available at L stations) gives the standard 2.50 USD fare with free transfers within two hours. A 1-day unlimited pass is 5 USD; a 3-day pass is 15 USD.
Divvy bike-share has stations throughout the city and is genuinely practical for the flat terrain of the Lakefront Trail and the near north side; a 24-hour pass costs around 15 USD. Uber and Lyft work normally.
Chicago does not have a reputation as a walkable city, but the area from Millennium Park north to the Gold Coast along the lake is very walkable, as is Wicker Park and the West Loop.
The Lakefront and Loop
The lakefront is Chicago’s best feature and the one that visitors from cities without it tend to underestimate. Lake Michigan is not a lake in the way most lakes are - from any point on the shoreline, there is no visible far bank, and in the morning light it can convincingly resemble an ocean. The Lakefront Trail runs 26 km and is shared by cyclists and pedestrians; in summer it is heavily used on weekends and easier to enjoy on weekday mornings.
Millennium Park, off Michigan Avenue, holds Cloud Gate (the reflective bean-shaped sculpture by Anish Kapoor), the Jay Pritzker Pavilion (a Frank Gehry-designed outdoor concert hall where the Grant Park Orchestra plays free concerts on summer evenings), and the Crown Fountain. The park is free and busy; the most useful thing to know is that the Grant Park evening concerts are genuinely excellent and deeply underused by visitors who do not know they are happening.
The Loop is Chicago’s downtown core. The best way to understand the architecture is from street level rather than an observatory: walk along LaSalle Street (the financial canyon), stand under the elevated train tracks at Wabash and Lake, and look up at the Rookery Building (1888), the oldest surviving skyscraper in the city. The Willis Tower (formerly Sears) has an observation deck on the 103rd floor with retractable glass balconies (Skydeck, around 30 USD); on a clear day you can see four states.
Architecture
Chicago invented the steel-frame skyscraper and subsequently spent 130 years producing more significant buildings per square kilometer than almost anywhere in the world. The Chicago Architecture Center on Wacker Drive runs river boat cruises that are the best 90-minute investment a visitor can make: a volunteer docent (trained to CAC standards) narrates the city’s architectural history as the boat moves through the river system under buildings you cannot properly see from street level. Tickets run 46 to 60 USD for adults; book in advance in summer as tours fill up. The same organisation runs architectural walking tours for less money if boats are not your preference.
Art Institute of Chicago
One of the great art museums in North America, located directly on Michigan Avenue at the edge of Millennium Park. The permanent collection spans ancient artefacts to 20th-century American art; the Impressionist collection is particularly strong (Seurat’s “A Sunday on La Grande Jatte” and several major Monets). Admission is around 26 USD for adults; children under 14 are free. Illinois residents have free access on certain days. Book timed-entry tickets online to avoid queues on weekends.
Neighbourhoods
The Loop: Financial and theatre district; most hotels and major attractions are here or just north.
River North: Gallery district and mid-to-high-end restaurants; convenient but touristy.
Gold Coast: Wealthy residential neighbourhood north of the Loop with excellent independent restaurants on and around Rush Street.
Wicker Park and Bucktown: The best independent neighbourhood for bars, restaurants, vintage shops, and music venues. Accessible by Blue Line to Damen. Has been gentrifying for twenty years but still has character.
Logan Square: Further west, more local, cheaper, and increasingly the address of interesting new restaurants. Blue Line to Logan Square.
West Loop: The neighbourhood that has seen the most dramatic restaurant development in the last decade. Fulton Market Street has a dense concentration of serious restaurants in a former meat-packing district.
Hyde Park: South Side neighbourhood that is home to the University of Chicago and the Museum of Science and Industry; far from the tourist core but genuinely different in character.
Where to Eat
Deep-dish pizza: Chicago’s most famous food is also its most debated. Deep-dish is more of a casserole than a pizza - thick, buttery crust, cheese on the bottom, chunky tomato sauce on top - and locals themselves are divided on whether it is actually the city’s best offering. Lou Malnati’s on Wells Street is the most reliable address; a medium pizza costs around 20 USD. Pequod’s in Lincoln Park has a cult following for its caramelised cheese crust. Neither is everyday food for locals, who largely eat thin-crust Chicago-style pizza.
Italian beef sandwich: This is the more genuinely local daily food: thinly sliced beef, slow-cooked in seasoned jus, piled into Italian bread and served “wet” (dipped in the jus) or “dry,” with sweet peppers or hot giardiniera. Al’s Beef has been at the original Taylor Street location since 1938 and charges around 11 USD for the standard sandwich. Order it wet with hot giardiniera to eat it correctly.
Serious dining: The West Loop and Fulton Market are the address for Chicago’s most interesting restaurants in 2025. Monteverde (Chef Sarah Grueneberg, James Beard Award winner) on Randolph Street serves inventive Italian-American pasta at mid-range prices. Alinea remains one of a handful of three-Michelin-star restaurants in the US; the tasting menu runs 300 USD or more per person and requires advance reservations months out. Girl and the Goat on Randolph Street is Stephanie Izard’s flagship and reliably one of the best-value serious meals in the neighbourhood at around 60 to 80 USD per person.
Breakfast and coffee: Intelligentsia Coffee, founded in Chicago in 1995, helped define the third-wave coffee movement in the US; the Millennium Park and Wicker Park locations are good starting points.
Where to Stay
The Loop and Michigan Avenue: Most business hotels and several good independent options. The Langham Chicago, in a Mies van der Rohe-designed IBM building on Wacker Drive, is the best luxury hotel in the city. The Hotel Allegro in the Loop is a mid-range arts-themed option at lower prices.
River North: Dense with hotels at various price points. Convenient for the Magnificent Mile shopping district and walking distance from everything in the Loop.
Wicker Park: Limited hotel options but the neighbourhood itself rewards staying here if you prioritise bars, restaurants, and independent shops over proximity to the major museums. Airbnb availability is high.
Things to Know
Weather: Chicago’s climate is extreme by most visitors’ standards. Summers can reach 38C with high humidity; winters regularly drop below minus 15C with windchill that makes it feel far colder. Spring and autumn are short, genuinely pleasant, and the best time to visit. The city’s “windy city” nickname has nothing to do with literal wind (Chicago is not even in the top ten windiest US cities) and is variously attributed to 19th-century political boosterism.
Tipping: 18 to 20 percent is standard at restaurants, more at high-end places. One to two dollars per drink at bars. Taxi and rideshare tips of 15 to 20 percent are expected.
Safety: Chicago has a serious violent crime problem in specific neighbourhoods, overwhelmingly concentrated on the South and West Sides in areas that visitors are unlikely to encounter on a tourist itinerary. The Loop, North Michigan Avenue, River North, Lincoln Park, Wicker Park, and the lakefront are all low-crime areas with heavy foot traffic. The most practical advice is to be aware of your immediate surroundings at night and use Uber/Lyft rather than walking long distances in unfamiliar areas after midnight.
Free things worth doing: Lincoln Park Zoo (free, genuinely good), the Lakefront Trail, Grant Park Orchestra concerts (Thursday and Saturday evenings, summer), Chicago Cultural Center (free art exhibitions in a stunning Beaux-Arts building near Millennium Park).