Having visited Chicago briefly once before for a Summer trip throughout America I knew that it was always somewhere I would like to go back and see. I didn’t actually get to do much in terms of tourist activities the first time around either so when I knew I was going back I was excited to get the opportunity to see a bit more!

Chicago Skyline
View From Our Apartment Rooftop at Sunset

The city is clean, impressive and very friendly. Huge sky scrapers tower throughout the city but with a completely different feel to somewhere like Manhattan. The whole pace of the city is much, much slower with a lot less people while still having that big city feeling to it. It’s funny because there is both a lot and a little to do in the city I feel. It’s somewhere you will never get bored of, but having been twice I can say that

Here are some of the things that I did while I was in Chicago, along with some of the activities that were recommended to me but unfortunately I didn’t get to do for myself!

Willis Tower Sky Deck

Willis Tower Sky Deck

The Sky Deck in Chicago is definitely a must do. This towering building is the tallest observation deck in North America and standing at a whopping 103 floors up, you will really feel it! The elevator takes your directly to the 103rd floor where you will be greeted with windows along each wall giving you a full panoramic view of Chicago. Then, you can join the line for your chance to stand on the glass 4.5 foot box hanging on the outside of the building. You only get 90 seconds on the ledge to take pictures and soak up the view, which honestly can feel a little rushed when you are in a group of people all wanted to get pictures in various poses. Our time was so rushed I felt like I didn’t properly get to take in the view at all, but in saying that I am still very happy that we did it. Tickets range from $25 per person all the way to $75 for a fast pass. You can find tickets and more details of the experience on their website here

John Hancock Building

The 360 CHICAGO observation deck is located 1000 feet above the famed Magnificent Mile in the iconic John Hancock Building. This deck offers breathtaking 360 degrees views of the city skyline and Lake Michigan. If you are looking for more of a thrill, 360 Chicago observation deck is also home of TILT, an enclosed moving platform that literally tilts you out over Michigan Avenue from the 94th Floor! You can plan your visit here! Neither of these tickle your fancy? Get the view without the price by visiting their bar on the 95th floor where you can have a drink and soak up the scenery from above!

Boat Tours from Navy Pier

Taking a boat tour from the bright blue waters of Navy Pier is a must do when you visit the city of Chicago. There is no way of saying that boat tours aren’t your thing, because there are just so many types to choose from!

Shoreline Sightseeing run a number of tours daily including their Architecture River Tour, Classic Lakes Tour, Lake Fireworks Tour and Architecture Fireworks Tour. I took the Archiecture River Tour which costs $40 and is honestly worth every penney. Not only does this tour give you amazing views of the entire city that you would not see anywhere else, but you also learn more about the city that you could have ever imagined. It’s a great way to spend 90 minutes of your time in the city, so definitely do it – or one of the tours if you get the opportunity.

Navy Pier

Navy Pier, Chiago

Speaking of boat tours from Navy pier, Navy Pier itself is somewhere that definitely has to be explored. On the waterfront with spectacular views of the cities skyline, you can get much more picturesque than here! Filled with amazing things to do throughout the summer months along with biweekly Aon Summer Fireworks shows occuring on Wednesdays and Saturdays throughout the summer. Find out the full list of events on their website here!

‘The Bean’

Cloud Gate

Cloud Gate is a sculpture located in Millenium Park, nicknamed and more commonly known as ‘The Bean’. Made up of 168 stainless steel plates welded together seemlesly, this sculpture is really something to behold. It measures 33 by 66 by 42 feet, and weighs 110 tons. There isn’t much to do there in all honesty apart from admire it, walk around it and take pictures in the reflection but it is one of the must do things to do in Chicago none the less.

Grant Park


Grant park is Chicagos beautiful answer to Central Park. Boasting blissful areas of greenery and walkways, it’s one of the best places to escape the city. This urban park spans across 319 acres of the city. Located within the central business district, the parks most notable features are areas such as Millenium Park, the Buckingham Fountain and the Art Institute of Chicago. It’s a must visit when you come to the city! During the year there are also festivals and events held inside this park such as Lollapalooza

Shedd Aquarium

Moving town towards the other side of the city you have the Shedd Aquarium, one of the worlds largest indoor aquariums. General admission for this attraction is quite steep at $39.95 for an adult and $29.95 for a child, but you are guaranteed to be immersed in the world below the sea on this visit. Find out more about the aquarium and what it has to offer here!

Adler Planetarium

The Adler Planetarium is a public museum dedicated to the study of astronomy and astrophysics. If this is the kind of thing that interests you then this attraction is mind blowing! It is one of the coolest things to do in Chicago in my opinion and with general admission starting at just $12 it is affordable as well. Plan your visit and find out more about the Planetarium and all of the experiences that they offer here!

These are just some of the things that I have gotten a chance to do while in Chicago between the two trips that I have taken. There are plenty more amazing things to do around the city. If sports is your thing (or even if it’s not!) you can go to an NBA game with the Chicago Bulls in the United Centre or visit the Chicago Cubs at Wrigley Field for some baseball. If you are looking to soak up the sun in the Summer then make sure to find a good spot to lie on North Avenue Beach where you have the beautiful water of Michigan lake in front of you, and a view of skyscrapers behind you! The list is really endless when it comes to this beautiful city!

Also a side note for anyone wanted to travel to Chicago during St.Patricks weekend. This is the weekend that my friends and I decided to travel for and it was really, really good fun. We stayed in this apartment that gave us a birds eye view of the boats dying the river at 9am that morning – something we saw hundreds of people queuing for downstairs while we got to look while still in our PJs! St.Patricks day itself we found to be very hectic. There were queueus for 100+ people out of the best Irish bars in the city and everywhere that didn’t have a queue was ticket-only. Part of this was our own fault for not planning accordingly, but we really did underestimate just how much they love Paddys Day over there! If you are planning a visit make sure to either be willing to queue at the bar you want at 7am that morning, or else sign yourself up to a ticketed event somewhere in the city. In saying that, going over for this day is still really good craic, so I’d definitely recommend it (just maybe be a little bit more organised than we were!). Two good Irish bars to go to are Fado and The Kerryman.

So tell me, have you ever been to Chicago? Or would you like to go? For me, I can honestly say that out of the 10+ states that I have visited so far, it is hands down my favourite!

*Most of these images were taken by my sister, who is a photographer. You can find her work here

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