Chicago is a wonderful mix of world renowned sights, an instantly recognisable skyline, stunning architecture and incredible art works. It’s no wonder I lost my heart to the Windy City where there really is something for everyone.
1 | Cloud Gate aka ‘the Bean’
Top of the list has to be Cloud Gate, also known as the Bean. Chicago is synonymous with the Bean and there’s something strangely compelling about the smooth silver sculpture inspired by liquid mercury and which perfectly reflects the stunning Chicago skyline and the clouds above.
So simple yet so amazing, the Bean is a definite Chicago must see. Be sure to check out the arch which serves as a gate underneath the bean and warps and multiplies reflections.
Cloud Gate, located at AT&T Plaza, Millennium Park (Michigan Avenue between Washington and Madison)
2| The Chicago Skyline
The Chicago skyline is easily one of the world’s most recognisable skylines and includes two of the three tallest buildings in the US, the Willis Tower and the Trump International Hotel and Tower. Other big names include the John Hancock Tower and the Aon Centre. The skyline is best appreciated from a distance and the views are incredible from both a Lake Michigan cruise and the Signature Lounge in the John Hancock Tower.
From Lake Michigan:
From the Signature Lounge, John Hancock Centre (see number 8!): 
3| Art Institute of Chicago
I should confess that I’m not the biggest art enthusiast in the world but I was drawn to the Chicago Art Institute by the lure of some of my favourite paintings hanging in the halls. And then I ended up spending half a day taking in the Monets, Van Goghs and Warhols to name a few. The Art institute is home to a treasure trove of amazing art work and was an unexpected treat in my Chicago sightseeing trail. Serious art lovers should budget a serious amount of time for a visit!
The Bedroom, Van Gogh:
Sunday Afternoon on the Island of La Grande Jatte, Georges Seurat:
Art Institute of Chicago, located at 111 South Michigan Avenue (at Adams)
While visiting the Art Institute check out Crown Fountain, the rest of Grant Park and the Chess Party:
4| Crown Fountain
The 50 foot high glass towers project faces behind the water using LEDS and, as well as cascading down the towers, on occasion the water spouts out of the mouth of the subject. It’s a fun place to hang out and people watch!
Crown Fountain, Millennium Park, Michigan Avenue between Madison and Monroe
5| Other Grant Park attractions
If you want to tick some of Chicago’s most famous attractions of your sightseeing list then Grant Park is the place to go. It’s packed full to the brim with some of Chicago’s best loved landmarks including the Bean and the world renowned Art Institute of Chicago. Gehry’s intricate band shell, the BP Bridge and Buckingham Fountain are among the attractions housed in Chicago’s ‘front yard’.
Grant Park, Michigan Avenue between Roosevelt and Randolph
6| Touch And Go Chess Party
The Chess Party hangs out down by the Art Institute and, if chess is your thing, for $2 you can play until your heart is content. And even if chess isn’t your thing it’s still pretty cool to stand and admire the unique Chicago attraction.
Touch and Go Chess Party, Michigan Avenue just south of the Art Institute of Chicago
7| Lake Michigan
Lake Michigan is one of the five Great Lakes of North America and the Windy City is most definitely windy along its shores! The sheer size of the lake is mesmerising and the shades of blue are spectacular. The view is stunning from the Signature Lounge in the John Hancock Centre and a cruise on the lake is a lovely way to spend an afternoon.
8| Signature Lounge, John Hancock Centre
Located in one of the tallest buildings in Chicago the Signature Lounge has amazing views across the city. The lounge is situated an ear popping 1,000 feet in the sky on the 96th floor of the John Hancock Center and a restaurant is below on 95. The cocktails and mocktails we sampled were excellent. Go early to avoid the long queues, the Signature Lounge is a popular spot. Check out our Signature Lounge adventure here!
The John Hancock Centre is also home to the observation deck at 360 Chicago and its soon to open attraction, Tilt, an enclosed steel and glass platform that will tilt over the city and give downward facing views of Chicago. I’m game for that!
The Signature Lounge, Michigan Avenue between Delaware and Chestnut
9| Public Art
Don’t miss the public art installations dotted around the city. The streets of Chicago are like an open air museum of sculptures and murals by artists including Picasso and Miro and we had great fun wandering around discovering these gems. And the best bit? They’re totally free! Check out our favourite public art installations in Chicago here!
The 70 foot long Four Seasons mural by Marc Chagall (Dearborn between Monroe and Madison):
The Picasso (Dearborn between Washington and Randolph):
10| The Architecture
The skyscrapers in Chicago are phenomenal with an incredibly diverse mix of styles. A crick in the neck is inevitable from staring skywards! Chicago is the birthplace of the skyscraper and it is defined by its architecture. The city has had a huge influence on modern architecture across the US and it is home to the signature buildings of a host of prominent architects.
The corn cob towers of Marina City (300 North State Street):
11| The Chicago River
I live in Ireland. Of course I love a river which is turned green for St Patrick’s Day! Other than that, the Chicago River and its bridges are a great vantage point from which to observe the wall of skyscrapers lining the city. Check out Michigan Avenue Bridge for some stunning views of the city. Grab a ticket for the Chicago Architecture Foundation River Cruise, it’s a great way to check out the architecture and get up close and personal with the Chicago River!
12| Cupcake ATM
I know it’s not exactly a world renowned tourist sight but there aren’t many places where you can purchase a cupcake in an ATM Machine at any time of the day or night. It takes 10 seconds and the swipe of a credit card and, voila, a beautifully boxed cupcake arrives. Pure genius by Sparkles. the original cupcake bakery. Don’t underestimate the novelty of a Cupcake ATM!
There’s even one for the dog, swoon!
Sprinkles, 50 East Walton Street
13| The Puppet Bike
If you want to find your inner child in Chicago then keep a look out for The Puppet Bike. It’s a mobile stage with a cast of animal themed puppets who perform to music and playfully interact with the audience giving lots of laughs along the way. Think they’re worth a dollar? Watch as they scurry down to collect it and reward you with a pat on the head or a selfie telling you you’re beautiful! The Puppet Bike makes me happy!
14| Shopping
There are a lot of things I love to do and shopping is one of them. In fact it features highly on my list of favourite things and Chicago doesn’t disappoint on the retail therapy front. From the world famous Magnificent Mile on Michigan Avenue to downtown State Street Chicago is a shopping mecca. If Macy’s is on your list of shopping destinations be sure to check out the Tiffany ceiling made up of over 1.6 million pieces of favrile glass.
Magnificent Mile:
Tiffany dome at Macy’s:
15| Navy Pier
Situated on the shores of Lake Michigan, Navy Pier is a board walk playground with attractions including the Navy Pier Ferris Wheel and the Museum of Stained Glass Windows. The views of the city and Lake Michigan are a nice bonus!
There you have it, Chicago in 15 fantastic sights. It’s an amazing city to visit and a place to feel instantly at home despite just stepping off the plane. Do remember: Chicago has harsh winters so, unless you are very brave, plan your visits for the more pleasant seasons!
I am going to Chicago in June so this has given me an idea of where to start for my sightseeing.
Xoxo
It’s such a fab city, hope you have a ball x
What a city! Definitely worth a visit,