Grand station (CTA Red Line)

Grand Avenue is a major east-west street in the city of Chicago and nearby DuPage County, although it deviates somewhat from Chicago's grid system, as it is diagonal west of Western Avenue. The street runs from the Kingery Highway (also known as U.S. Route 20 and Illinois Route 83) in Addison, east through the western suburbs, and then east-southeast into Chicago, through the Magnificent Mile shopping area, and continuing out to Navy Pier, where it ends. This is a distance of about 19 miles (31 km).

Grand Plaza is a residential apartment building in Chicago, Illinois, United States. The 57 story building was completed in 2003 at a height of 641 feet (195 m) when measured from its decorative spires. Grand Plaza I is one of the tallest all-residential buildings in Chicago and contains 481 luxury apartment units. Until July 1st, 2008, it was the tallest building in the Chicago ZIP Code 60610, the ZIP Code with the most high-rises in the city. On July 1st, 2008, the building ended up being in a new ZIP Code: 60654. That ZIP Code encompasses a small area, so the building is still the tallest in its ZIP Code. Phase two of the Grand Plaza complex was The Residences at Grand Plaza, completed in the same year. At 39 floors, it is the shorter of the two twin towers and is now a condominium building. Both buildings were designed by Loewenberg + Associates and OWP&P Architects. They also share a common base full of retail such as a Jewel-Osco supermarket.

The Tokyo Hotel, located at 19 E. Ohio Street, was a hotel in the Near North Side of Chicago. Designed by architect Ralph C. Harris, it is 15 stories tall, and has 150 rooms. It opened in 1927 as the Devonshire Hotel. Before it closed in 2013, the Tokyo was not aimed at tourists, but rather longer-term residents, and earned a reputation for being home to "prostitution and criminal activity." In October 2013 the hotel was sold for $13.5 Million to a real estate development firm. Following extensive renovation, the building reopened in June 2015 as the Freehand Chicago Hostel.

The Tree Studio Building and Annexes was an artist colony established in Chicago, Illinois in 1894 by Judge Lambert Tree and his wife, Anne Tree.

The Medinah Temple is a large Moorish Revival building in Chicago built by Shriners architects Huehl and Schmidt in 1912. It is located on the Near North Side of Chicago, Illinois at 600 N. Wabash Avenue, extending from Ohio Street to Ontario Street. In 2022, it was announced that the site will temporarily house a casino while the $1.7B Bally's Casino is under construction nearby.

Hubbard Street is a street in Chicago, Illinois named for early settler Gurdon Saltonstall Hubbard. Hubbard Street has three distinct sections. The first, east of the Chicago River, runs from Kingsbury Street to Michigan Avenue. The second, longer section runs from Des Plaines Street west to Campbell Avenue (2500 W) The third and shortest section is a three-block stretch from Kilpatrick Avenue (4700 W) to Lavergne Avenue (5000 W) where it ends at the Hubbard Playlot Park. Notable buildings on this street include Courthouse Place at 54 W. Hubbard.

Millennium Centre is a postmodern skyscraper in Chicago, Illinois in the city's Near North Side neighborhood. The building rises 610 feet (186 m). It contains 59 floors, and was completed in 2003. The architectural firm who designed the building was Solomon Cordwell Buenz & Associates. Millennium Centre notably sold over 95% of its 350 residential units in September 2000, only two days after the developer had released information about the proposed structure; this occurred before the building had even been approved for construction by the City of Chicago. The building's design incorporates a high-rise park on the roof of the 14th floor, with six two-story townhomes circling the park. Millennium Centre is topped off by a 10-foot (3 m) illuminated spire, which is included in the building's structural height.

Andy's Jazz Club, located several blocks north of the Chicago Loop, was founded as "Andy's 11 E. Lounge" in 1951 by Andy Rizzuto. A group of investors bought the property in 1975, changing its name to "Andy's". The club is one of the city's most popular jazz venues.In 1977 jazz promoters Penny Tyler and John Defauw began producing midday jazz sessions at Andy's, which was later expanded to include performances later in the day with sets at 5pm and 9pm. The 5pm performance - known as "Jazz at Five" - has since become a Chicago tradition.Performers at the club have included Larry Coryell, Franz Jackson, Von Freeman, and Joey DeFrancesco.

Urban Prep Academies (also known as Urban Prep Charter Academy for Young Men or simply Urban Prep) is a nonprofit organization that operates a network of free open-enrollment public all-male college-preparatory high schools in Chicago. Founded in 2002, and receiving its first charter approval from Chicago Public Schools in 2005, it operates the first all-male public charter high school in the United States. The network opened a second campus in 2009 and a third in August 2010. From 2010–2019, 100% of the seniors in the school's graduating classes were admitted to four-year colleges or universities.

The Boyce Building is an historic building in Chicago, Illinois, associated with William D. Boyce and his publishing house, which catered to small towns. The building was also the headquarters of his Lone Scouts of America.

Plaza 440 is a 49-story residential condominium building located in downtown Chicago, Illinois. Originally built in 1992, it underwent a condominium conversion in 2005. The building contains 457 residential units and shares a 2,000,000-square-foot (190,000 m2) mixed-use development with a 336-room Marriott hotel and a 400-space parking garage. It rises from the northwest corner of Wabash and Hubbard streets in the River North district of Chicago's Near North Side. Plaza 440 was designed by Solomon, Cordwell, Buenz and Associates, built by the John Buck Company and originally managed by its subsidiary, the John Buck Management Group. The building opened to residents in October 1991, but construction was not fully completed until 1992. 90% of the building's units were leased by August 1992. Plaza 440 was the last residential high-rise built in Chicago for years to come.The building was sold to American Invsco in September 2004 at a price of US$107 million. The previous owners, Archstone-Smith, had purchased the building two years previously for US$24 million. This is the current equivalent of US$154 million and US$36 million, respectively.

Jazz Showcase is one of the oldest jazz clubs in Chicago, Illinois, founded in 1947 by NEA Jazz Master Joe Segal, whose son Wayne now owns and operates the venue. Segal's various showcases have served as a launch pad for a number of career jazz musicians.