Loop

public park, opened in 2014. There is an ice skating ribbon, which is used for rollerblading in summer, a climbing wall and a 3 acre play garden.

Built in 1897 as Chicago's first public library, the building now houses the city's Visitor Information Center, galleries, and exhibit halls. Worth a visit to see the beautiful interior — the ceiling of Preston Bradley Hall includes a 38-foot Tiffany glass dome, and the north wing includes the impressive Grand Army of the Republic Rotunda. Of late, amid various city-approved art and music events, some surprisingly good theater has been performed here.

The 4th Floor Visitor Gallery is temporarily closed.

Once the tallest building in the world, the Sears Tower (officially renamed the Willis Tower) now has to settle for second-highest in the Americas alone, behind New York City's One World Trade Center (and even those are after a semantic battle with Toronto and the CN Tower). The Hancock Observatory (see Near North) has a nicer view of the city, but the Sears Tower offers an incredible view of its own from "The Ledge", which lets visitors walk out in a transparent balcony suspended 1,353 feet above the street. To avoid the crowds, visit after 4PM.

Runs numerous river cruises and themed architecture walks covering the Loop and other parts of the city, with offerings suitable for general audiences and people with specific interests. There are some small, informative exhibits inside their 224 S Michigan headquarters and a gift shop. Walking tours are usually $15, $12 for students/seniors.

A beautiful Art Deco tower covered in dark green terra cotta and adorned with a gold terra cotta leaf at the pinnacle. It is rumored that the architects (the sons of city planner Daniel Burnham) intended the building to resemble a bottle of champagne. It's in great condition today, and can be visited through one of the bars in the lobby of the hotel inside.

This plaza includes Mies' Dirksen Federal Building and Kluczynski Federal Building (built eleven years apart), with a low-rise post office enveloped in their sleek black lines. But the buildings are not quite as famous as the gigantic red constructivist flamingo statue by Alexander Calder in the plaza in front of the post office. An adventurous raccoon may have set a raccoon world climbing record by reaching the scaffolding on the 36th floor in 2006.

A Michigan Avenue charmer built in 1884-85 whose worn stone walls looks even older. Even though few artists could afford to keep studios on Michigan Avenue these days, it still has a creative air, thanks to the fanciful carvings on the walls.

Louis Sullivan designed the northernmost (18) of the three buildings here, and the team of Holabird & Roche added the next two (24 & 30). The roots of Mies-style modernism are easily apparent in the immaculate proportions here, although Sullivan's piers overflow like water-pipes with ornament at the top, and Holabird & Roche's two make an interesting contrast with the master.

Designed by John Mills van Osdel, the city's first accredited architect after the Chicago Fire, this four-story building is one of the oldest in the Loop. The two bottom floors were remodeled by Louis Sullivan in 1896, adding some interesting cast-iron designs for its use as a department store.

Louis Sullivan was only a draftsman at the time this was built, but there are some interesting designs nestled into expressive façade and the classic, powerful masonry walls.

It's partially obscured by renovations, but this first-wave skyscraper still makes an immediate contrast with the modern Federal Center across the street. The lobby is decorated with Tiffany mosaics and bronze carvings of Pere Marquette, an early French explorer. There is plenty of first-floor retail to allow trips inside.

Named appropriately for a mountain in New Hampshire, the Monadnock was the last tall building to be supported by its own walls (not a metal frame, although the 1893 addition by Holabird & Roche does use one). It's a masterpiece of simplicity and power in form. The block-long hallway that serves as a lobby has incredible ambiance: it's always kept at a level of brightness that suggests gas lamps, and the small stores on the first floor (a coffee shop, a shoe-shine, a restaurant) are all turn-of-the-century tile-and-polish.

A then-unprecedented amount of glass was used in this early skyscraper, bewildering a public still used to masonry walls. Note the difference between the first two floors and the ones above: hold-outs among the previous building's tenants forced developers to build the foundation and the first two floors under the top three floors from the old building, and then knock off the top three when their leases had expired. It was restored when it became the Hotel Burnham (see below) in 1999, and can be explored with a stop at the Atwood Cafe (also below).

The Rookery is gorgeous to the point of absurdity, with delight to be found in details in the rustic lower walls and the triumphant upper walls. (Note the helpful street names carved in the corners.) Named for pigeons' habit of roosting in the then-new skyscrapers, this was the first Loop building to be granted preservation status in 1972. The lobby was remodeled in 1907 by enfant terrible Frank Lloyd Wright, adding his own touch to the interior.

961 ft. For a time this was the tallest building in the world without an official name, although locals know exactly what to call it: The White Castle Building. It is distinctive for its "crown," which is brightly illuminated at night. If you are nearby, head into its lobby to see its enormous indoor garden and fountain.

1136 ft. Built as the Standard Oil Building, the Aon Center is America's sixth tallest building from base to roof, after the Empire State Building in New York City, and fifteenth tallest in the world by architectural detail. It was built in 1972 by architect Edward Stone and initially was faced with marble, but the windy city began to blow the marble off the sides of the building. The entire building had to be refaced with granite — a costly job at one-half of the entire building costs! A walk around the base can be particularly gratifying to admire the uninterrupted views straight up the shear walls and the "musical sculptures.".

823 ft. The biggest American project ever to be headed by a woman, Jeanne Gang's skyscraper was named the world's best new building by Emporis when it opened in 2009 (four spots ahead of the Trump Tower across the river). Its most distinguishing feature is its series of undulating balconies, which extend as far as twelve feet from the building's walls, giving the building a surreal "rippling" effect. It uses an unforgettable curtain wall that compliments wavy balconies. Though impressive from any angle, it's best viewed relative to the water — either from a boat tour or the riverwalk over in the Near North.

1007 ft. Built by Adrian Smith in 1989, the granite-clad AT&T Corporate Center is one of the city's more distinctive skyscrapers for its massive size, spiked roof pinnacles, and a style evocative of both Gothic and Japanese architectural styles. It's not well-known, but it is the eighth tallest building in the U.S.

850 ft. Located at the exact center of CTA's Loop transit system, this building is distinctive for its vertical curve. It has been renamed for each of the successive banks that have bought out its previous tenants — for example, it was the BankOne Tower until 2005. The plaza outside is more interesting than the interior — it is home to an enormous mosaic by renowned Russian painter Marc Chagall.

648 ft. The 1965 Daley Center is Chicago's principal civic center and boasts a gigantic Picasso statue on the adjacent plaza. A true Chicago landmark, the Daley Center was featured in The Blues Brothers, who drive across Daley Plaza and crash through the glass walls of the building. The Mies-esque design was intended to age visibly: the color has faded in a rust-like direction from exposure to the elements.

287 ft. While not very tall, this 1975 brutalist structure is one of the most distinctive and curious in the Chicago skyline. As its name suggests, it is a vertical prison skyscraper and its sharp triangular shape is designed to minimize the amount of time that it takes to patrol its corridors. Its prisoners have some of the prison world's best views as their exercise yard is on top of the roof, although the narrow slits serving as windows do not allow such nice views from the cells. The prison houses male and female convicts of all security levels, waiting for transport to the courthouse nearby.

582 ft. Anyone who has seen Adventures in Babysitting should immediately recognize this 1984 building, as its slanted roof (lit up at night) played a very important role in the film's climax. It's a hard building to miss, as it is just across the street from Millennium Park.

Dankmar Adler and Louis Sullivan's masterpiece. Frank Lloyd Wright, who served as an apprentice on the project, called it "The greatest room for music and opera in the world — bar none." If the current production isn't worth seeing, take a tour of this gorgeous, acoustically-perfect theater instead. Tours are available at various times and days depending on the season.

A Broadway in Chicago outlet, this opulent theater was built in 1926 for the vaudeville circuit and is now glossed up for high-profile productions with 2,300 seats per show. The Producers and the mighty Oprah's The Color Purple both enjoyed long runs here.

Home of Chicago's renowned orchestra; they spend a lot of time on the road, though, so visiting orchestras and stately jazz concerts can also be found here, as can the occasional curveball like a silent film.

An old Balaban & Katz movie palace, refurbished as one of the city's premier performance venues. It hosts a wide range of events, from spoken word and stand-up comedy to jazz, gospel, and rock. Most people, however, know it for the iconic marquee out front.

The Oriental Theater was once Chicago's most ornate movie palace, but this is now another Broadway in Chicago theater outlet.

Non-profit theater company in an extremely expensive space; they pride themselves on new works, but are better known for revivals of plays from the American theater canon. Post-show discussions with the cast are held after Wednesday and Thursday night performances.

Another Broadway in Chicago theater. Founded in 1906 to attract a classier vaudeville crowd, it saw performances from Harry Houdini, and was run by New York theater impresario Sam Shubert for more than forty-five years. In modern times, Monty Python's Spamalot and High School Musical have played here.

Extraordinary productions of major operas, in the impressive Civic Opera House, overlooking the river; local legend has it that the back-story behind business magnate Samuel Insull's decision to build it was the inspiration for the opera scenes in Citizen Kane. Although highly acclaimed today, there was a minor controversy among purists when they began to project English titles above the stage for non-English operas.

The Civic Opera House is also home to the Joffrey Ballet, one of the premier ballet companies in the United States. They are best known for their annual performance of The Nutcracker for the Christmas season.

Chicago has a large Irish-American population, and it's one that punches above its weight — St Patrick's Day is a huge affair in the Windy City. The endless parade takes place on Columbus Drive along the Chicago River, which is dyed green for the occasion. The river dyeing is at 10:45AM, and the parade starts at noon. These festivities take place on the Saturday before the holiday.

The world's biggest free outdoor gospel festival is in Grant Park! Like the Blues Fest, the performers are a combination of national and local acts. Chicago has a thriving gospel scene and this is one of the best ways to experience it for the uninitiated.

Top national and local blues musicians perform all day long throughout the festival just a couple miles from where modern blues was born. This is the world's premiere blues festival, and the list of greats who have performed here (like Albert King, B.B. King, Buddy Guy, Chuck Berry, Etta James, John Lee Hooker, Memphis Slim, Stevie Ray Vaughan, Willie Dixon) gets more impressive each successive year. Admission is free and the performances are spread out across six stages throughout Grant Park.

An outdoor showcase of Chicago restaurants, vendors, and performers, plus big name concerts. The specifics of the scheme vary from year to year, but generally, you buy a roll of tickets and then trade in those tickets for beer, drinks, food, and desserts. It's a great chance to sample the range of Chicago cuisine (at steeper prices). Also a great opportunity to watch Independence Day fireworks from the park and lakefront, but beware: it gets crowded.

Chicago is spoiled for free music in the summer – the excellent Grant Park Symphony Orchestra plays in Millennium Park's Pritzker Pavilion about three times per week June–August, usually W,F Sa. The symphony is hardly the only free show at the Pritzker Pavilion, though, and it's worth walking by on any night around 6:30PM to see if any other classical, dance, etc. performances are running.

Formerly a traveling tour, Lollapalooza has now found a permanent location in Chicago and grown quite a bit. It's a massive three day collection of popular and lesser-known national and local rock and hip hop bands.

The great Chicago Jazz Festival was inaugurated in 1974 just weeks after Duke Ellington's death to commemorate his life's work, and has since become one of the world's largest annual jazz festivals, pulling some of the biggest names in the jazz world each year. And this one is free. If you have the means, you might want to come earlier in the week — there are usually a host of jazz-related events in the run up to the festival.