Skip to main content.

Top 10 historic things to do in Chicago

Hotel search

Book your Chicago hotel for hot dogs in one of baseball’s oldest parks, a river tour through a century of architecture, and authentic Chicago blues in a legendary club. Time travel to the past with this guide to the best of historic Chicago.

The birth of baseball at Wrigley Field

Baseball was practically invented in Chicago’s Wrigley Field. Since 1913, the Chicago Cubs have made this ivy-clad ballpark their home. Grab a steaming hot dog, a cold beer and a bleacher seat. Come early for a tour of more than 90 years of baseball history.

1060 W. Addison St.

Touring Chicago’s gangster past

While the city has moved on since the gangster days of Al Capone and John Dillinger, you can revisit those times with a trip to the Chicago’s Roaring ‘20s museum. Take one of the Untouchable Tours and see where John Dillinger made his last stand and step on the site of the infamous St. Valentine’s Day Massacre.

Singing the Chicago blues at Buddy Guy’s Legends

The cool, electric urban blues scene that formed here with Muddy Waters, Howlin’ Wolf and Koko Taylor is alive and well at Buddy Guy’s Legends blues bar. Come for some saucy Louisiana barbecue and some stinging Chicago blues, maybe even from the namesake guitarist himself.

754 S. Wabash Avenue


Cheeseburgers at the Billy Goat

Since 1964, newspaper reporters have come to trade gossip at this hole-in-the-wall spot, immortalized on Saturday Night Live by late comedian John Belushi. Griddle-fried burgers are the specialty, while people-watching is the favorite pastime.

430 N. Michigan Avenue, lower level


A river tour of Chicago’s skyscrapers

A myriad of architectural styles, from Gothic temples to soaring modern skyscrapers, form downtown Chicago’s impressive skyline. To get a close-up view of the best examples, take a daytime architecture tour of the Chicago River, and watch the sun flicker off the buildings.

224 S. Michigan Avenue


Shopping history at Macy’s

For more than 100 years, Marshall Fields was the first stop for everything from furs to couture accessories. Macy’s, the building’s new tenant, upholds that tradition, down to Field’s famous Fango mints. You can still even get a birds-eye view of the Tiffany Dome from the fifth floor.

111 N. State Street, Loop

Deep dish pizza where it all began

Rich, gooey and crammed full of sauce and cheese, the deep dish pizza is a Chicago staple. Dig in at the place where it started, Pizzeria Uno. Bring your appetite and patience as a wait is common.

29 E. Ohio Street

Old Chicago at the Museum of Science and Industry

Chicago circa 1910 is lovingly recreated at the Museum of Science and Industry. Old fashioned storefronts, displaying period fashions and technology, line the cobblestone streets and are illuminated by iron lamps. The museum itself, with its opulent Fairy Castle and a working Boeing 727, deserves an entire day to explore.

5700 S. Lake Shore Drive, Hyde Park

An afternoon in Grant Park

Between Lake Michigan’s sparkling blue waters and the towering spires of downtown sits Grant Park. This pristine park, filled with monuments, gardens and walking paths shaded by 100-year-old elm trees, has been the city’s most popular playground for over 150 years.

Tour Chicago’s ethnic heritage

Chicago’s heritage stands out in its distinct ethnic neighborhoods. Start with Little Italy or Pilsen, the former with its Italian restaurants and ice cream counters, the latter with its Mexican murals and art museum.