Chicago, Illinois
Chicago: The City That Rebuilt Itself Into a Laboratory
The Great Chicago Fire of 1871 burned for two days and destroyed roughly a third of the city. The standard story is that this blank slate gave architects the freedom to invent the modern skyscraper. The actual story is more interesting: immediately after the fire, reconstruction looked almost identical to what had been there before. The architectural revolution that followed took a decade and came not from the fire itself but from the convergence of new steel technology, new elevator designs, and a generation of architects determined to stop copying European models. William Le Baron Jenney, Daniel Burnham, Louis Sullivan, and others produced what became known as the Chicago School, and the buildings they put up in the 1880s and 1890s are the reason the city looks the way it does today. One of those buildings, the Montauk of 1882, was the first in the world constructed at night, using a new technique involving electric lighting, because the client needed it finished in under a year.
Understanding that history makes Chicago’s architecture far more interesting than it appears on a standard itinerary. The city is not just skyline photography. It is a working argument about what buildings can be.
Getting There and Getting Around
O’Hare International Airport (ORD) and Midway Airport (MDW) both serve Chicago. O’Hare handles the larger volume of international and domestic flights. The Blue Line CTA train runs from O’Hare directly into the Loop in about 45 minutes and costs around 5 USD. Taxis and rideshares from O’Hare run 40-60 USD depending on traffic.
Chicago’s public transit network (CTA) covers the city well. The elevated train loop around the downtown district serves most major destinations. A Ventra card (reloadable transit card) is the most practical way to pay; single rides are around 2.50 USD. The city is also walkable within neighbourhoods, though the distances between neighbourhoods are larger than they appear on maps.
What to See
Cloud Gate (The Bean)
The reflective ellipse in Millennium Park is free to visit and accessible daily. Its surface distorts and multiplies the skyline around it in ways that are genuinely difficult to predict. It is one of the most-photographed objects in the country, and it is better seen early in the morning before it becomes fully surrounded. The wider Millennium Park grounds include the Crown Fountain (two facing video towers that periodically project water) and the Frank Gehry-designed Jay Pritzker Pavilion, which hosts free outdoor concerts through the summer.
Skydeck Chicago at Willis Tower
The 103rd floor observation deck of Willis Tower (what many still call the Sears Tower) sits 412 metres above street level. Standard adult tickets cost around 32 USD, with expedited entry at roughly 55 USD. The Ledge, glass-floored boxes that extend out from the building’s face, are included in all tickets. Open Sunday through Friday from 9am, Saturday from 8:30am, closing at 10pm. Book online; queues for walk-up purchases on summer weekends can be long.
Art Institute of Chicago
One of the ten largest art museums in the United States, with particularly strong holdings in Impressionism (Seurat’s A Sunday on La Grande Jatte, Grant Wood’s American Gothic, Nighthawks by Edward Hopper). Adult admission is around 32 USD. The Modern Wing, designed by Renzo Piano and opened in 2009, is architecturally worth the visit on its own terms regardless of what is on display.
Architecture River Cruise
The Chicago Architecture Center runs a 90-minute guided cruise along all three branches of the Chicago River, covering around 50 buildings across six river miles. Votes consistently place this among the best city tours in the United States. Adult fares run approximately 42-58 USD depending on time and season. Book at least three to five days ahead for summer weekends and two weeks ahead for sunset sailings, which sell out earliest. The cruise is the most efficient way to understand Chicago’s architectural periods in sequence; the docent guides are trained specifically for this route and the quality of commentary is generally high.
Wrigley Field
Built in 1914, the home of the Chicago Cubs is the second-oldest ballpark in Major League Baseball. Even if baseball is not the draw, the stadium itself and the Wrigleyville neighbourhood surrounding it are worth seeing. Game tickets vary widely by opponent; seats in the upper deck for a non-premium game can be found under 30 USD. The rooftop bars on Sheffield and Waveland Avenues, on buildings directly across from the stadium, are a Chicago-specific experience with views directly into the outfield.
Navy Pier
The 1,011-metre pier extending into Lake Michigan was a logistics hub during both World Wars before its conversion to a public attraction in the 1990s. The Chicago Shakespeare Theater operates on the pier and is the strongest cultural institution there. The Ferris wheel and seasonal outdoor concerts make it heavily trafficked in summer; it is better visited on weekday mornings. The free lakefront path running south from Navy Pier toward Grant Park offers some of the best unobstructed skyline views in the city.
Neighbourhoods
The Loop
Downtown Chicago, bounded by the elevated train tracks, is where most major institutions are concentrated: the Art Institute, Millennium Park, the Chicago Riverwalk, and the majority of the iconic early skyscrapers. The Rookery Building (1888), the Monadnock Building (1891-1893), and the Carson Pirie Scott building (now Sullivan Center, 1899) are the most significant surviving examples of early Chicago School work and can be seen on foot in an afternoon.
Wicker Park and Bucktown
North and northwest of downtown, these adjacent neighbourhoods shifted from Eastern European working-class communities to artist enclaves in the 1980s and 1990s and have continued gentrifying since. The intersection of Milwaukee, North, and Damen Avenues is the commercial centre. Good independent restaurants, record shops, and vintage clothing stores cluster here. More affordable than Lincoln Park or River North.
Logan Square
Further northwest along the Milwaukee Avenue corridor, Logan Square has the best combination of neighbourhood character and food quality in the city. The boulevards here were designed in the 1870s as part of the same city planning project that produced Lincoln Park. The restaurant and bar scene is dense and consistently good.
Lincoln Park
The largest of Chicago’s 77 community areas, Lincoln Park is bounded to the east by the lake and the park of the same name. The free Lincoln Park Zoo (open year-round) is one of only a handful of major free zoos in the United States. The conservatory and the lakefront running and cycling paths are the other main draws.
Where to Eat
Lou Malnati’s
The most reliable of the major deep-dish pizza chains, with multiple locations across the city. The chain started in 1971 and uses a butter crust recipe that has not significantly changed. Deep-dish pizza takes 30-45 minutes to bake; plan accordingly and do not order it on a schedule. Lunch service during weekdays is faster than dinner.
Milly’s Pizza in the Pan
A newer and smaller operation that many food writers now consider the best deep-dish in the city. Milly’s makes a limited number of pizzas each day, around 45, so ordering ahead is strongly recommended. The crust and sauce balance is particularly good.
Pequod’s Pizza
In Lincoln Park, known for a caramelised cheese crust where the cheese extends to the pan edges and browns against the metal. This produces a different texture from the standard deep-dish and has a significant local following.
The Goods Shed (equivalent: The Purple Pig)
The Purple Pig on Michigan Avenue serves a broad menu of Mediterranean-influenced small plates with a particularly good wine list. It operates on a no-reservations basis and the waits at peak times are real but not extreme. Better for lunch or early dinner than peak evening.
Bavette’s Bar and Boeuf
A steak-focused restaurant in River North with a deliberately old-fashioned bar atmosphere. Appeared on the World’s 101 Best Steak Restaurants list in 2025. The bone-in ribeye is the thing to order. Reservations are essential; book at least two weeks ahead.
Chicago Hot Dog
The Vienna Beef hot dog on a poppy seed bun with yellow mustard, neon relish, diced onion, tomato wedges, a sport pepper, and celery salt is one of the most opinionated regional food traditions in the United States. Ketchup is not offered and is not welcome. Gene & Jude’s in River Grove (northwest of the city) is considered the purest expression of the form. Portillo’s has multiple Chicago locations and is more convenient.
Where to Stay
The Peninsula Chicago
On Michigan Avenue at the north end of the Magnificent Mile, the Peninsula consistently ranks among the best hotels in the city. Rooms are large by Chicago standards and the service record is strong. Premium pricing; expect over 400 USD per night for a standard room in summer.
Thompson Hotel Chicago
In the Gold Coast neighbourhood a short walk from the Magnificent Mile, the Thompson offers a good balance of style and price for mid-range travellers. The rooftop bar operates seasonally.
The Freehand Chicago
A shared-space hotel in the River North neighbourhood with private rooms as well as hostel-style accommodation. Rates for private rooms start lower than most mid-range hotels in the area. The bar and common areas are well-designed and the location is useful.
HI Chicago Hostel
In the South Loop, one of the better-run hostels in the Midwest. Dormitory beds from around 40 USD per night. Lockers, a communal kitchen, and good transport links make it practical for budget travellers.
Practical Tips
Best Time to Visit
Late May and June, and September through October, give the most comfortable weather. July and August are hot and humid but peak for outdoor concerts and lakefront activity. January through March is genuinely cold (temperatures regularly below freezing, sometimes well below) and some outdoor attractions close or reduce hours. The St. Patrick’s Day river dyeing in March, when the Chicago River is dyed green, draws large crowds and is an event unique to the city.
The CityPASS
The Chicago CityPASS bundles admission to Skydeck Chicago (with expedited entry), the Art Institute, the Field Museum, and two additional attractions at roughly half the combined walk-up price. Adult passes run around 144 USD for the standard version. Worth it if you plan to visit at least three of the included sites in a single trip.
Architecture on Foot
The Chicago Architecture Center (at 111 East Wacker Drive, riverfront) sells self-guided tour maps and operates ticketed walking tours in addition to the river cruise. The free Riverwalk along the south bank of the Chicago River between Lake Shore Drive and Lake Street passes the most concentrated stretch of significant buildings and can be walked independently.
Day trips worth the time include Indiana Dunes National Park, about 90 minutes by South Shore Line commuter rail from Millennium Station. The dunes and lakefront beaches there are less crowded than Chicago’s own beaches in summer and the park is genuinely scenic.