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Grayland is a Metra commuter railroad station in the Old Irving Park neighborhood in Chicago, Illinois, along the Milwaukee District North Line. It is located at 3729 North Kilbourn Avenue, is 8.2 miles (13.2 km) away from Chicago Union Station, the southern terminus of the line, and serves commuters between Union Station and Fox Lake, Illinois. In Metra's zone-based fare system, Grayland is in zone B. As of 2018, Grayland is the 132nd busiest of Metra's 236 non-downtown stations, with an average of 357 weekday boardings.As of December 12, 2022, Grayland is served by 40 trains (19 inbound, 21 outbound) on weekdays, by all 20 trains (10 in each direction) on Saturdays, and by all 18 trains (nine in each direction) on Sundays and holidays. The station is an open platform shelter near the Union Pacific Railroad crossing/remote-Tower A-5. Parking is available on Kilbourn Avenue along the west side of the tracks south of Milwaukee Avenue, and on-street parking is also available on Kilbourn Avenue along the east side of the tracks north of Milwaukee Avenue. The station was opened in 1873 to service Grayland, at the time a suburb of Chicago (annexed in 1889) created by subdividing John Gray's farm. Gray deeded the land the already built depot was on to the Chicago, Milwaukee & St. Paul Railroad in return for a promise to maintain and service the depot, thus insuring that the inhabitants of Gray's subdivision would have easy transport to Chicago and back.

The Charles N. Loucks House is a historic house at 3926 N. Keeler Avenue in the Irving Park neighborhood of Chicago, Illinois. The house was built in 1889 for Charles N. Loucks, a real estate planner who developed much of Irving Park, and his family. Clarence H. Tabor, an architect who worked for Loucks' real estate company, designed the Queen Anne house. The house's design features a front porch with carved wooden trim and a pediment, a front-facing gable with a floral design at its peak, and a tower with a conical roof. The interior includes distinctive floral-patterned art glass windows, which include both clear and stained glass and were inspired by English and Japanese design.The house was added to the National Register of Historic Places on February 9, 1984.

The Race House is an Italianate style house located at 3945 North Tripp Avenue in the Irving Park neighborhood of Chicago, Illinois, United States. The house was built in 1874 by an unknown architect for Stephen A. Race. It was designated a Chicago Landmark on September 22, 1988.

Irving Park is one of 77 officially designated Chicago community areas located on the Northwest Side. It is bounded by the Chicago River on the east, the Milwaukee Road railroad tracks on the west, Addison Street on the south and Montrose Avenue on the north, west of Pulaski Road stretching to encompass the region between Belmont Avenue on the south and, roughly, Leland Avenue on the north. It is named after the American author Washington Irving. Old Irving Park, bounded by Montrose Avenue, Pulaski Road, Addison Street, and Cicero Avenue, has a variety of housing stock with Queen Anne, Victorian, and Italianate homes, a few farmhouses, and numerous bungalows. The CTA Blue Line runs through this neighborhood with stops at Addison, Irving Park, and Montrose.

The Whistle Stop Inn is a two-story building in Chicago, Illinois, which has been the home of a variety of businesses. Built in 1889 in the Irving Park neighborhood, this place represents a type of intimate neighborhood storefront that was common but is now rare. The Whistle Stop Inn was designated a Chicago Landmark in 1990. It is at 4200 W. Irving Park Road, just off the Kennedy Expressway.

Irving Park is a railroad station on Metra's Union Pacific Northwest Line located in the Irving Park neighborhood of Chicago, Illinois. The station is elevated on a solid-fill embankment which parallels the Kennedy Expressway. It is located adjacent to a station of the same name on the Blue Line. The station contains two side platforms; the southwest platform serves outbound trains, and the northeast platform serves inbound trains. A third express track runs through Irving Park but does not stop there. Irving Park is located in the B zone in Metra's zone-based fare system. As of 2018, Irving Park is the 110th busiest of Metra's 236 non-downtown stations, with an average of 439 weekday boardings.Irving Park is 6.9 miles (11.1 km) from Ogilvie Transportation Center and 56.2 miles (90.4 km) from Harvard. As of April 3, 2023, Irving Park is served by 50 trains (25 in each direction) on weekdays, by 31 trains (16 inbound, 15 outbound) on Saturdays, and by 19 trains (nine inbound, 10 outbound) on Sundays. Weekend inbound train No. 706 stops at Irving Park on days with home Cubs games only. Otherwise, this train bypasses Irving Park.

The Elmer C. Jensen House was built in 1905. It was designed by, and built for, architect Elmer C. Jensen. It is located in the Old Irving Park neighborhood of Chicago, Illinois, United States.

Irving Park is an 'L' station on the CTA's Blue Line. The station is located in the median of the Kennedy Expressway in the Irving Park neighborhood, though it draws its name from its cross street. Irving Park is one of two stations on the Blue Line that stops in an expressway median where the entrance is below the platform; Rosemont is the other, specifically beneath the westbound lane of the Kennedy Expressway. The station opened in 1970 as a part of the Kennedy extension of the Milwaukee Elevated from Logan Square to Jefferson Park.

The Villa District, also known as Villa Historic District, (Polish: Polskie Wille) is a historic district in Chicago, Illinois, United States. It is located on Chicago's Northwest Side within the community area of Irving Park. Its borders are along Pulaski Road to the west, the Union Pacific/Northwest rail line to the north, Hamlin Avenue to the east, and Addison Street to the south. Located directly north of the Wacławowo area of Avondale, the Villa District is serviced by the Blue Line's Addison street station. The district was built in 1902 by a number of architects, many of them visibly influenced by Frank Lloyd Wright's Prairie Style of architecture. Most notable among these were bungalows designed by the architectural firm of Hatzfeld and Knox, whose partner Clarence Hatzfeld would later design the fieldhouse and natatorium at Portage Park. The area was originally developed as the "Villa addition to Irving Park" and showcases many unique Craftsman and Prairie style homes fronting on picturesque boulevard style streets. Although St. Wenceslaus church, a majestic Romanesque-Art Deco hybrid draws many of the tourists visiting the area, this historic church is actually a few blocks south of the district's formal boundaries. The Villa district was the northwest "bookend" for Chicago's vaunted Polish Corridor along Milwaukee Avenue that extended from Division and Ashland Avenue at Polonia Triangle. Journalist Mike Royko famously dubbed the area as the Polish Kenilworth after the posh suburb of Chicago's North Shore. The Villa Historic District was added to the National Register of Historic Places on September 11, 1979. Its area was increased on March 10, 1983 by the addition of the Villa Apartments, 3948-3952 and 3949-3953 W. Waveland Ave.The Villa District was designated a Chicago Landmark on November 23, 1983.

The Ropp-Grabill House is a historic house in the Irving Park neighborhood of Chicago, Illinois. While the house's construction date and original owners are unclear, it was built sometime in the early 1870s, making it part of the first wave of development in Irving Park. At the time, the neighborhood was still meant to be a wealthy garden suburb of Chicago, and it was not until later in the century that it became a dense neighborhood of the city. The house was designed in the Italianate style, a popular choice at the time, and includes oriel windows on its south side, bracketed eaves, and a cupola. Its name comes from two of its longtime tenants; the Ropp family lived in the house from 1891 until 1943, while the Grabill family lived there from 1943 through 1977.The house was added to the National Register of Historic Places on April 15, 1985.

The Milford Theatre was a movie palace located at 3311 N. Pulaski Road (originally Crawford Avenue), in the Avondale neighborhood of Chicago. Constructed in 1917, like the Portage Theater, it was designed by Henry L. Newhouse and opened for the Ascher Brothers circuit.The theatre had 1,150 seats, no balcony and a single screen. Because of the area's large Polish population, a significant share of the screenings were Polish films, drawing even street photographer Vivian Maier. When not screening Polish films, the Milford showed Hollywood productions at extremely low ticket prices, charging only 60 cents for admission deep into the 1970s. On February 27, 1981, famed Polish singer and guitarist Krzysztof Klenczon was seriously injured by a drunk driver in Chicago, en route from the Milford Ballroom that was part of the complex. Klenczon died on April 7 at St. Joseph's Hospital in Chicago, and was buried July 25, 1981, in his family's plot in Szczytno, Poland.The theater remained open until 1990, and was demolished four years later after a fire.

The Florsheim Shoe Company Building is a former factory for the Florsheim Shoe Company and a Chicago Landmark in the Avondale neighborhood. The building was built between 1924 and 1926 when the Florsheim Shoe Company had "2,500 employees, 71 retail outlets, 9,000 dealers and a network of regional wholesale distributors". The architect of the building was Alfred S. Alschuler, who designed numerous Chicago Landmarks and buildings on the National Register of Historic Places. The building was a factory for Florsheim until 1986, when it became the warehouse for a records management. The building, located on the 3900 block of West Belmont Avenue, is now luxury lofts. The Commission on Chicago Landmarks designated the building a Chicago Landmark on March 29, 2006.