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15 amazing things to do in Chicago

Birthplace of the skyscraper and home to blues music, deep dish pizza and the Bulls, Chicago is a fantastic choice for a USA city break. The Windy city is a whirlwind of culture, with world class art galleries, iconic architecture and 77 distinct communities from Greektown to the Black Metropolis. If you're overwhelmed deciding what to do in Chicago, we've narrowed it down a handy list of 15 unmissable attractions in America's Second City.


1. Head up the Willis Tower

Formerly known as Sears Tower, you can take an elevator to the 103rd floor to visit the Skydeck observation floor. On a clear day you can see four different states! Even if it's cloudy, the views straight down to the cars below is jaw dropping, especially if you venture out onto the Ledge, a glass box jutting out 4 feet into nothingness, 1,353 feet above the ground. On your way to the lift you'll make your way through the Chicago Experience, a fun interactive multimedia exhibition celebrating Chicago's history, architecture and famous faces including the Obamas, Oprah and Michael Jordan.


2. Eat deep dish pizza

Ask someone to name an iconic Chicago dish, odds are they will say deep dish pizza. Tons of cheese and toppings with a crunchy crust, it's gooey, chewy heaven. Iconic pizza restaurant Pizzeria Uno claims to have invented the style in 1943, and other popular places to indulge include Pequod's, Gino's East, Bartoli's and local chain, Giordano's.


As it happens, Chicago is a great destination for foodies. Check out our blog to discover 5 essential Chicagoan dishes you need to try, from Al's Italian Beef sandwich to how to eat your hot dog Chicago style.


3. Visit the Shedd Aquarium

One of our favourite things to do in Chicago, the Shedd aquarium is focussed on conservation and reducing plastic, and have a huge range of habitats and creatures to see, including beluga whales, white sided dolphins and sea otters.

Opened in 1930, the salt water needed for the exhibits was brought by train from Key West!


Wander around massive tanks full of beautiful corals, a rescued green sea turtle and several species of shark, and enjoy the Abbott Oceanarium where you can watch Pacific white-sided dolphins and beluga whales, both from above and below water.


NB: If you're visiting the Shedd Aquarium, we'd recommend buying a Go City pass - it also covers the Field Museum next door as well as the Skydeck and 360 Chicago observation decks (all included on this list!). The Aquarium is only included on the All Inclusive Go City pass, not the Explorer pass, and you need to pre book a free arrival time slot on the Go City app. You could also check out our blog about getting the most out of a one day Go City pass.


4. Get your culture fix at the Art Institute

Up there with the Louvre, the Uffizi, London's National Gallery and the Met, the Chicago Art Institute is one of the world's great galleries and has a fabulous collection of famous masterpieces. Featuring work by Warhol, Picasso, Monet, Seurat, Pissarro, Manet, Matisse, Pollock, here is where you can see Nighthawks by Edward Hopper, American Gothic by Grant Wood and Seurat’s A Sunday Afternoon on the Island of La Grande Jatte.

5. Take a stroll down Navy Pier

Take a walk down Navy Pier for beautiful views of Chicago's skyline and out across Lake Michigan. In the summer there are fair ground rides and this is also where you'll find the Chicago Shakespeare Theatre.

An icy walk along the river

6. Scout out iconic Architecture with a river walk

Chicago is the birthplace of the skyscraper. Following the Great Chicago Fire in 1871, which destroyed more than 3 square miles of the city, and another major fire just 3 years later, a massive rebuild was put in place using more modern, fire resistant materials. Sturdy steel frames allowed buildings to grow taller and have larger windows, leading to the world's first skyscrapers.


Key architectural highlights on the Magnificent Mile and along the river include the Chicago Tribune Tower, the futuristic Marina City, (known locally as the Corn Cobs), the towering glass Trump Tower and the Wrigley Building. The riverside walk is a great way to see these buildings by foot, and in the summer you can take a boat tour.


7. Take a trip to Bronzeville

Leave the centre of Chicago and visit the south side. Bronzeville is African American neighbourhood, once known as the Black Metropolis, which formed following the Great Northern Migration of black Americans in the early 20th century as they escaped the segregation of the South. You'll find delicious soul food and beautiful street art, and see if you can find the former homes of Nat King Cole and Louis Armstrong!

Colourful street art in Bronzeville

8. Visit the dinosaurs at the Field Museum

Like a cross between London's British Museum and Natural History Museum, the Field Museum houses over 20 million specimens of zoology, anthropology, botany and geology. Head to the main hall to marvel at the dino skeleton nicknamed Maximo. He's a Titanosaur, the largest creature ever to walk the earth! Another famous resident is Sue, the world's largest and most complete T-Rex skeleton.


The museum has a huge collection of amazing dinosaur skeletons and fossils, and other highlights include exhibitions about meteorites, plants of the world, the history and culture of the Pacific Islands, Ancient Egypt (see 23 mummies and a three storey replica of a tomb), and a beautiful collection of gems - the original collection was displayed at the 1893 World’s Columbian Exposition by Tiffany & Co. before being bought and donated to the museum.


9. Take a photo at the Cloud Gate AKA the Bean

This shiny art installation was only placed in Millennium Park in 2006 but immediately became an iconic Chicago landmark. Known locally as the Bean, you can walk underneath the sculpture where the mirrored surface will reflect you multiple times in a mad kaleidoscope pattern, or sit back and enjoy the clouds and skyscrapers reflected in the shine sides.

Bean there, done that!

10. Cheer on the Chicago Bulls

This was an absolute must for us - David has been a huge fan since the Michael Jordan days of his 90s childhood and so watching a game at United Centre was like a pilgrimage for him. If Basketball isn't your thing, Chicago is home to several world class sports teams, from the Cubs (baseball) to the Bears (football) to the Blackhawks (ice hockey).


11. Head up the John Hancock Tower after dark

Ok, so it's technically called 875 North Michigan Avenue now - the building formerly known as the John Hancock Centre has another amazing observation deck. At just 100m lower than the Skydeck at the Willis Tower, Chicago 360 is located on the 94th floor and gives sweeping views across the whole city. Bonus, you can also see the Willis Tower from up here! We'd recommend going up after dark to see the illuminated skyline and city lights stretching for miles.


On the L looking back towards the river

12. Snap a picture of the Chicago Theatre

The bright lights of the Chicago Theatre will make you feel like you're on New York's Broadway! This popular landmark is on North State Street, right next to the State/Lake 'L' station and dates from 1921.


13. Ride the 'L' around the Loop.

The L (short for Elevated) is Chicago's rapid transit system which covers most of the city and suburbs. The Loop is a historic raised section covering the heart of Downtown Chicago. The one way loop route itself is only about 1.78 miles long and takes less than 10 minutes to ride.


NB: the Loop is not an enclosed circuit - it leaves the route and heads off into the city at top left and bottom right corners. This means you can't just sit on one train the whole way round, but riding the whole loop is really easy: board a Pink Line train at Randolph and take that to Quincy. At Quincy, change to an Orange Line train and ride the loop back round to where you started! Quincy station is particularly beautiful as it has been restored to its original 1897 appearance, including a tin roof and even vintage ad posters.


14. Walk the lakefront

The promenade running along Lake Michigan is a popular place for cyclists and joggers, and you can stroll from the Shedd Aquarium back towards the city for beautiful views of the skyline and Navy Pier. In winter months the lake often has pack ice floating on the surface - wrap up warm, the winds off the lake can be freezing!

A chilly January day on Lake Michigan

15. Get the Blues

The Chicago blues are as iconic to the city as deep dish pizza. Famous for electric guitars and harmonicas, big names such as Muddy Waters, Bo Diddley, Buddy Guy and Howlin' Wolf spread the electric sound around the world, and there are several venues in Chicago where you can enjoy some music with a few drinks.

Where to hear Blues in Chicago - our top pick is Kingston Mines, slightly further out from the centre in Lincoln Park: this venue has two stages and has alternating sets of live music on the go all night from 7pm until the early hours. It has a terrific atmosphere and attracts really top notch musicians.


Other great options are House of Blues, Blue Chicago, Buddy Guy's (the legend himself plays here in January, book well in advance!), and every June there is a free Blues festival in Millennium Park!


Under current city mandates at time of writing, indoor dining, bars, museums and galleries mentioned in this blog no longer require masks and proof of vaccination for entry, but there are some exceptions (we believe the United Center still requires proof of vaccine or a negative test). Check local advice before your trip to stay up to date!


Related content: Wondering where to stay in Chicago? Check out our review of the St Clair Hotel








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