Top 10 things to do in Chicago

The Windy City in the American Mid-west has long been a massive draw for anyone interested in visiting the Great Lakes, which lie along the border with Canada.

‘Can’t miss’ highlights include: taking in a ball game, visiting the zoo and discovering a live music scene that manages to switch effortlessly from classical to hip-hop in the twinkling of an eye.

With an incredible array of boutique shops and fine-dining restaurants, featured along the Magnificent Mile and State Street, it’s easy to see how Chicago has been built to impress and with a whole host of museums and galleries offering more high-brow alternatives, this is where people come to see and be seen.

If you’ve got plans to find out what all the fuss is about then below are 10 awesome options for things to do in Chicago and from cubs to stuffed crusts, get ready for an experience that will quite literally blow your socks off.

chicago downtown chicago


Take in ball game

Trips to Chicago are totally unfulfilled without a visit to the world-famous Wrigley Field baseball stadium, the home of the Chicago Cubs. With an enviable history that stretches back to the 1870’s it’s quite evident that baseball means much more to the locals than simply a mere game and a tour of the stadium will no doubt enforce this point of view. So, get yourself a couple of tickets to a game, head to West Addison Street and grab yourself a foot-long because right here is where you get to learn about a part of American culture that’s as essential as mom’s apple pie.


Delve a little deeper

Stuffed crusts and deep-pan are both words associated with one of Chicago’s most delicious exports and if you really want to get under the cheesy skin of what makes the Windy City tick then chomping into a pizza has to be top of your list of things to do. The home of the world’s very first deep-dish pizza is reputed to be Pizzeria Uno which is still operating today under the new name of Uno Chicago Grill. All things considered, enjoying a deep-pan pizza anywhere in Chicago is worthwhile however, check out the Loop community south of Lincoln Park for some of the best pizzerias.


Go Bears!

In the 80’s the likes of William ‘The Fridge’ Perry were pretty much world-famous and American Football was known the world over for its half-time razzmatazz and larger than life characters. The Chicago Bears last won the Super Bowl in 1985 but this hasn’t stopped the allure of the game with rivals such as the Green Bay Packers and the Detroit Lions making up the numbers on many memorable occasions. If you’re in town then catching a game is simply going to be a unique experience that you’ll never forget. Just remember to wrap up warm because Soldier Field (the oldest field in continuous operation) can get pretty chilly during the winter season.

chicago bears soldier field chicago


Enjoy a 360 degree view of the city

The only way is up - especially if you're hoping for jaw-dropping views of the city. Located 1000 feet above the Magnificent Mile, the 360 CHICAGO observation deck offers the most incredible views from as far as the eye can see, overlooking the soaring city skyline and across sparkling Lake Michigan. Fancy a bit more adrenaline? This observation deck is also home to TILT - Chicago's most heart-stopping thrill ride where an enclosed moving platform tilts you out over Michigan Avenue. The Sky Deck at Willis Tower offers sensational views too, with its glass balcony 'The Ledge' extending out four feet from the 103rd floor of Willis Tower.


The Magnificent Mile

With some of the country’s tallest buildings (the Hancock Centre and the Trump Hotel & Tower) it’s easy to understand how the Mag Mile got its name. This is where the rich and the famous come to shop, lunch and generally wonder amongst myriad designer names and fine-dining bolt-holes. Five-star hotels, gigantic malls and imposing architecture is the order of the day and if you’ve got the time, the money and the inclination then right here is where your dreams become reality.


Millennium Park

Located in the downtown Loop district, close to the shores of Lake Michigan, this urban patch of greenery was actually opened in 2004, just 4 years behind schedule. Don’t let such tardiness put you off visiting though as there’s loads to see and do amongst almost 25 acres of parkland, including: pavilions, ice rinks, outdoor theatres and fountains. There’s no better way to relax and unwind after a good day’s sightseeing and if you get to catch a live performance at the Jay Pritzker Pavilion then you’re in for a real treat and, quite possibly, the best picnic spot – ever. Cloud Gate (nicknamed 'The Bean') is one of the most popular attractions in the park - a giant sculpture giving the appearance of liquid mercury, this wonderful work of art has earned its place as one of the top selfie spots in the USA.


Lake Michigan

As the only one of the Great Lakes to be situated solely in US borders, Lake Michigan is unique and, with a length pushing further than 300 miles, it’s also huge. If you have the time to explore further afield from the sights of Chicago then the Great Lakes are a splendid choice and Michigan alone has plenty of beaches and scenic strolling ground from where to rest and relax within walking distance of the city. With such a vast coastline, it’s easy to see why Michigan is often referred to as America’s third coast and, as you’d expect, local beaches, such as: North Avenue and Montrose Avenue, can get pretty crowded during the summer months.


Navy Pier

Stretching over 1,000 metres into the gentle ripples of Lake Michigan, Navy Pier has long been Chicago’s undisputed attraction for tourists and locals alike. Ferris wheels, firework displays and even its own street car, all add up to a whole heap of riverside fun and with an Imax cinema and a stained-glass-window museum, thrown in for good measure, there’s literally something for everyone to enjoy. With rides, including: musical carousels, thrilling swingers and the Light Tower, the Navy Pier is a great option for visitors with families and you’ll also find loads of cruise ships and water taxis offering sightseeing tours and evening entertainment away from the board-walk.

chicago navy pier


Take in a live gig

As mentioned, Chicago’s got it going on when it comes to live sounds and from classical operettas in the park to dark and dingy jazz joints, there’s always something happening no matter what the time of day. Well known as being the birthplace of House music, you’ll still find plenty of clubs and venues offering exactly what Frankie Knuckles was pioneering back in the day and if you’re looking to hit the floor after dark then there’s no more authentic setting than Chicago. With hip-hop, soul, rap and, of course, jazz and the blues, all represented across the city, catching a live performance is a great way to end a day and, perhaps, start a morning.


The Chicago Art Institute

Located in Grant Park and housing more than 260,000 different pieces of artwork, no trip to Chicago is complete without a visit to this remarkable gallery. The collection spans some 5,000 years of work and includes classics, like: Edward Hopper’s Nighthawks and Van Gogh’s, post-impressionist masterpiece, Bedroom in Arles. From African American to Ancient Greek, American Gothic to Water Lilies, the Chicago Art Institute presents much more than a day’s worth of enjoyment for anyone who’s ever held a paintbrush.

modern wing art institute of chicago


Emma Bolton
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Emma Bolton
Call our travel experts now
01342 331798 Call us 9am-7pm Mon-Fri / 9am-5pm Sat-Sun