Chicago

Midwest

Chicago sits on the southwestern shore of Lake Michigan and is the third-largest city in the United States. Rebuilt after the Great Fire of 1871, the city became a laboratory for modern architecture — the world's first skyscraper was built here in 1885, and Chicago's skyline remains a textbook of 20th-century architectural innovation. The city's 77 officially recognized neighborhoods each have a distinct character, from the Polish heritage of Milwaukee Avenue to the jazz and blues clubs of Bronzeville to the glittering retail of Michigan Avenue. Chicago's museums — the Art Institute, the Field Museum, the Shedd Aquarium, the Adler Planetarium — are among the finest in North America. The Chicago River Architecture Boat Tour is considered one of the world's best urban tours.

Highlights

Magnificent MileMillennium Park & The BeanDeep Dish PizzaArchitecture Boat Tour

Must-Do Experiences

Take the Chicago Architecture Boat Tour

The Chicago Architecture Foundation's 90-minute river cruise through the downtown canyon of skyscrapers is consistently rated one of the world's best tours. Expert guides explain over 50 buildings from the water, providing context on Chicago's architectural legacy from Louis Sullivan and Frank Lloyd Wright to Mies van der Rohe and contemporary firms. Book in advance during summer. Tours depart from the Michigan Avenue bridge. From $45.

Experience Millennium Park

The 24.5-acre lakefront park is free and open year-round. Cloud Gate (universally known as 'the Bean') reflects the skyline in its polished steel surface for perfect selfies. The Jay Pritzker Pavilion hosts free summer concerts by the Grant Park Symphony Orchestra. In winter, the park's skating rink opens — free to skate (skate rental $13).

Visit the Art Institute of Chicago

One of the world's great art museums, housing pointillist masterpieces (Georges Seurat's A Sunday on La Grande Jatte), Grant Wood's American Gothic, Edward Hopper's Nighthawks, and extraordinary collections of Impressionist and Post-Impressionist works. The Modern Wing designed by Renzo Piano is particularly spectacular. Admission $25-35.

Eat Chicago Deep Dish Pizza

Chicago-style deep dish is not like any other pizza — a high-sided cast iron crust filled with layers of mozzarella, toppings, and chunky tomato sauce baked on top. Lou Malnati's, Giordano's, and Portillo's are the classic institutions. Deep dish takes 45 minutes to bake — order ahead. Most pies serve 2-4 people.

Best Time to Visit

June to August, September to October

spring

March-May: 35-65°F (2-18°C). Unpredictable — cold through March, improving in April and May. Chicago Marathon registration opens in spring.

summer

June-August: 75-90°F (24-32°C). Warm and sunny. Lake Michigan beaches are popular. Lollapalooza music festival in August.

autumn

September-October: 50-68°F (10-20°C). Beautiful fall colors, comfortable temperatures, excellent dining season.

winter

November-February: 20-38°F (-7 to 3°C). Very cold with wind chill. Indoor attractions are excellent. Christmas markets add charm. Lowest hotel rates.

Getting There

By Air

O'Hare International Airport (ORD) is a major international hub with direct flights to and from Europe, Asia, and throughout North America. The Blue Line CTA train connects O'Hare to downtown in 45 minutes for $5. Midway Airport (MDW) handles primarily domestic flights and connects to downtown via the Orange Line CTA in 30 minutes for $5. Taxi from O'Hare to downtown runs $40-55; rideshare $25-45.

By Train

Chicago is Amtrak's hub — more intercity trains originate and terminate here than any other city. Key routes: New York City (Lake Shore Limited, 19.5 hours), Washington DC (Capitol Limited, 17 hours), New Orleans (City of New Orleans, 19 hours), Los Angeles (Southwest Chief, 43 hours), and Seattle (Empire Builder, 46 hours). Chicago Union Station is a grand Beaux-Arts terminal worth visiting in its own right.

By Bus

Greyhound, FlixBus, and Megabus serve Chicago from Milwaukee (1.5 hours), Indianapolis (3 hours), Detroit (4.5 hours), and other Midwest cities at budget prices.

Budget Guide

Budget

$60-90/day

Mid-Range

$150-300/day

$$$

Luxury

$350-1200+/day

Neighborhoods

The Loop & Millennium Park

Chicago's downtown core, named for the elevated train (the 'L') that loops through it. The Millennium Park with its Cloud Gate sculpture (the 'Bean'), the Jay Pritzker Pavilion outdoor concert space, and the Crown Fountain anchor the park. Michigan Avenue, known as the Magnificent Mile, runs north from the Loop with flagship department stores, luxury boutiques, and the iconic Tribune Tower and Wrigley Building.

River North & Gold Coast

River North is Chicago's gallery district with hundreds of art galleries and some of the city's best restaurants. The Gold Coast along Lake Shore Drive is one of America's wealthiest neighborhoods, with magnificent 19th-century mansions, the Newberry Library, and Oak Street Beach at its northern end.

Wicker Park & Logan Square

Chicago's most vibrant bohemian neighborhoods west of downtown — Wicker Park's Division and Milwaukee Avenue corridors are packed with independent restaurants, vintage shops, live music venues, and bars. Logan Square has become Chicago's foodie destination with James Beard-nominated restaurants, craft breweries, and the Sunday farmers market.

Hyde Park & Museum Campus

The South Side neighborhood of Hyde Park is home to the University of Chicago and the outstanding Museum of Science and Industry. The Museum Campus along the lakefront south of downtown concentrates three world-class institutions: the Field Museum of Natural History, the Shedd Aquarium, and the Adler Planetarium.