Things to do in Chicago, Illinois

Things to do in Chicago, Illinois

If a trip to Chicago to catch an NFL game is something you’ve been thinking about, read on. This guide will help you make the most on exploring the area. If you’re looking for things to do in the Windy City, look no further as Ninety-Nine Yards writer Bryan Dickie gives you some top tips on what to do on a trip to Chicago.

Exploring Chicago

The USA’s third most populated City has plenty for visitors to do; from its skyscrapers to its over 8000 acres of parks, its restaurants and bars to its legendary sports teams.

On a clear day head to Navy Pier, which has numerous bars and restaurants for all tastes and from the end of which you can see for miles up the coast of Lake Michigan and gives a great view of the Chicago skyline.

A one mile walk/taxi from Navy Pier is 875 North Michigan Avenue, formerly the John Hancock Center. The 100 story skyscraper is the most northern of Chicago’s skyscrapers and offers fantastic views of the city. There’s the 360 Chicago experience which gives great views across the city or go to the signature bar on the 96th floor – it’s free to enter as long as you buy a drink (cheaper than the 360 entry fee!). While you’re north of the river check out the Magnificent Mile, Chicago’s premier commercial street. Hundreds of shops  to browse and upscale restaurants to eat in.

If one Skyscraper isn’t enough check out Willis Tower, the tallest building in Chicago and the third tallest in the USA. There’s no sneaky “ticket-less” bar on this one but it’s worth a trip up to the sky-deck where there observation boxes allow you to stand over the city.

For those looking for things much closer to sea level Chicago has nearly 8000 acres of park space. This includes the beautiful Millennium Park which includes the infamous Bean sculpture or its neighbour Grant Park with its stunning gardens and views of both the City and Lake Michigan.

Food and drink

Chicago is known for its deep dish pizza, not the “loads of extra dough, very bready” deep dish we get in the UK; but the inch and a half deep, cheese on the bottom, topping and tomato on the top, iron skillet baked deep dish pizza. Head to Giordano’s (there’s a few of them-the original near the Magnificent Mile) for some truly deep-dish Chicago pizza.

Ale fans will have heard of Goose Island, head to Goose Island itself for a freshly brewed beer at their in-brewery bar where their beers are rotated and changed daily and you may even have a chat with a chief brewer.


As you probably know Chicago has some of the most famed sports teams in the world: the Bears, Bulls, Cubs, Blackhawks and Whitesocks to name a few.

If you’re visiting in the summer make sure you head up to the legendary Wrigley Field, nestled in the quaintly named Wrigleyville, to catch a Cubs (baseball) game.

If you’re visiting early in the year head West from downtown Chicago to the United Center to take in a Bulls or Blackhawks (Ice Hockey) game. The Arena is filled with tributes to past greats including the legend that is Michael Jordan. Top tip: Head to the Kaiser Tiger (1415 W Randolph St) before the game for a huge selection of beers and food and a free lift to/from the Arena.

Or later in the year if football is your thing, head to Soldier Field for a bears game. Soldier Field is the oldest current NFL stadium, a real treat for the eyes and hell of an atmosphere regardless of who DA BEARS’ are playing.

Thinking of taking a trip stateside? Check out the Travel section to discover more about your team, it’s stadium and the incredible city they call home.

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