10 Famous Historical Places From Chicago's Past

Baseball was practically invented in Chicago’s Wrigley Field. Since 1913, the Chicago Cubs have made this ivy-clad ballpark their home. It’s the second oldest ballpark in MLB, so fans won’t want to miss it.

Over the years generations of fans have come to cheer on their team, and a host of famous players have filled the dugout. Get tickets to a game to experience the thrill for yourself. 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 including the infamous curse that was recently broken.

While the city has moved on since the gangster days of Al Capone and John Dillinger, you can revisit those days in multiple museums and historic sites in the city.

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. After that trip back in time, step through the green door of The Drifter speakeasy on North Orleans Street. While it’s been updated since, this bar occupies the same place as an authentic 1920s speakeasy and has a great rotating menu of cocktails.

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 famous guitarist himself.

Note that shows after 8 pm are over 21s only, but food is served until 11 pm so if you want a late night meal with a show, or just a slice of pie, Buddy Guy’s is the place to go.

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

The original tavern is located on the first floor of the Realtor Building on North Michigan Avenue and is still happy to provide mouthwatering burgers. There are also several other locations dotted throughout the city, including at Navy Pier, so wherever you are, there’s probably one nearby.

A myriad of architectural styles, from Gothic temples to soaring modern skyscrapers, form downtown Chicago’s impressive skyline. From the armchair-like Civic Opera House and the elaborate towers of the Wrigley Building, built in the 1920s, to the wavy organic lines of the modern Aqua tower, Chicago is a haven of soaring structures.

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. Be ready to take epic pictures of these architectural masterpieces as you pass them by.

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 5th floor.

Shopaholics won’t be able to resist a trip to this iconic American department store to shop to their hearts’ content. Take your time to explore the floors and browse the huge range of items on sale. You can even stop for a drink or something to eat while you’re there.

Rich, gooey and crammed full of sauce and cheese, the deep-dish pizza is a Chicago staple. It wouldn’t be a trip to the Windy City without a slice of this legendary local food. Dig in at the place where it started, Pizzeria Uno.

Originally created in 1943, the classic deep dish is still available to this day. Pick your choice of toppings or go for the original, whatever you choose, it’s pizza like you’ve never experienced it before. Bring your appetite and patience as a wait is common.

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.

This impressive building is found in the beautiful surroundings of Jackson Park, which was designed in 1871 and hosted the 1893 Worlds Fair, making it a place of historical interest itself.

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.

Stroll down the Lakeside Trail to take in the views of Lake Michigan, admire the spectacular rococo fountain and elegant rose garden, and take a look at the statues found around the park. It’s a lovely spot to find peace in the heart of the city.

Chicago’s heritage stands out in its distinct ethnic neighborhoods. The city has long been a hub for many different cultures and you can’t experience its history fully without exploring these too.

We’d recommend starting with Little Italy or Pilsen. Little Italy is home to some beautiful small parks, the historic Notre Dame de Chicago and Maxwell market, which dates back to 1900, as well as excellent restaurants and ice cream parlors. Over in Pilsen you’ll find colorful Mexican murals and the National Museum of Mexican Art.