Chinatown, Little Italy and Greektown Bike Ride: Three Districts, One Day

Three immigrant districts sit within a short ride of one another on the South and Near West Sides: Chinatown, Little Italy and Greektown. Each has a main street and a food tradition. Link them from south to north. The ride is part of Routes & Trails and pairs with the Chicago Riverwalk.

The 2013 map

In 2013 the Chicago Bike Station at Millennium Park offered free maps of self-guided rides, among them one for Greektown, Chinatown and Little Italy¹. The station no longer runs rides.

Chinatown

Chinatown lies in the Armour Square community area on the South Side². It formed around 1912, after settlers moved south from near the Loop². The On Leong Merchants Association had a building constructed along Cermak Road that year². Over a third of Chicago’s Chinese population lives in the district². The Chinatown Gate followed in 1975². Peter Fung designed it, and it spans Wentworth Avenue³. It is modeled after a gate in Beijing³.

Chinatown’s main stretch runs along Cermak Road and Wentworth Avenue⁵. Chinatown Square is a two-level mall, and the middle of the mall holds 12 Chinese zodiac statues^2,5.

Ping Tom Memorial Park and the Wells-Wentworth Connector

Ping Tom Memorial Park is a 17.24-acre park on the south bank of the Chicago River⁴. A rail track and 18th Street divide it into sections⁴. It features a pagoda-style pavilion and bamboo gardens⁴. It opened on October 2, 1999, and the boathouse opened on June 9, 2013⁴. In 1962 preparations for the Dan Ryan Expressway demolished Hardin Square and Stanford Parks⁴. The annual Dragon Boat Race event is held at the park⁵. A seasonal boat ferries visitors between the Loop and the park⁵.

In 2019 the city was finishing a realignment of the skewed Cermak and Wentworth intersection and had begun the Wells-Wentworth Connector, a new street linking Chinatown, downtown and The 78⁶. The 2019 design called for raised bike lanes on the sidewalks, separated from pedestrians by landscaping, and 140 trees planted between the lane and the street⁶. It also included speed tables⁶. A 2014 plan placed the roadway north under Roosevelt Road to meet Wells Street⁷. That year Streetsblog described Cermak as six lanes wide⁷. Cross it at the signal.

Little Italy and Taylor Street

The Italian population peaked in the 1950s and 1960s, and began to decline after the 1963 decision to build the University of Illinois there⁸. Chicago’s foreign-born Italian population peaked at 73,960 in 1930⁸. Several Italian restaurants and businesses remain on the Taylor Street corridor⁸.

By 1927 Italians owned 500 grocery stores and 257 restaurants in the city’s Italian neighborhoods⁸. Taylor Street is the heart of the neighborhood⁹. Conte di Savoia has been a staple since 1948⁹. For history, the free Jane Addams Hull House Museum is a memorial to the social reformer⁹. Hull House was co-founded in 1889¹². It became a National Historic Landmark on June 23, 1965¹². The National Public Housing Museum, also free, is nearby⁹. Maxwell Street Market is the city’s oldest open-air market⁹. Stroll Lexington Street for Italianate architecture, including the John Coughlan House, built in 1871⁹. Most Hull House buildings were demolished in the mid-1960s for the University of Illinois Chicago¹².

Greektown on Halsted

Greektown is a social and dining district on the Near West Side¹⁰. It runs along Halsted Street between Van Buren and Madison Streets¹⁰. The original Greektown on Halsted began with the Jane Addams Hull House, which was the Greek community’s meeting point¹⁰. Holy Trinity, the first Greek Orthodox church in the Midwest, was established in 1897¹⁰. The National Hellenic Museum stands at Halsted and Van Buren¹¹. It opened in its current building on December 10, 2011¹¹. An annual parade and festival remain¹⁰.

Putting it together

Begin at the Chinatown Gate and ride Wentworth to Ping Tom Park. Then head north to Taylor Street in Little Italy and finish on Halsted in Greektown. The Red Line stops around the clock at Cermak–Chinatown, so you can reach the start by train². The #24 bus serves Wentworth and the #44 serves Canal². Read the Chicago Riverwalk guide for a downtown link, then browse best bike rides in Chicago.