Working in travel, I’m fortunate to know people in other parts of the world, and a lot of my colleagues reside in Chicago.
For thanksgiving last year, I travelled to Chicago and spent a week with my friends from across the pond, exploring during the day and hanging out together in the evenings.
As a tourist, with also a lot of local knowledge thanks to my friends, my experience of Chicago was very well rounded.
I thought I’d compile my favourite activities into this blog, and all the information I found out for you all. (In no particular order)
Getting around
Chicago is a very well connected city, with busses and train systems connecting all parts of the city. Chicago is massive, so this is very useful when trying to get from point A to point B.
When I arrived, one of my friends told me about the app Ventra. Here I was able to purchase a transport card that was valid on all trains and busses for an unlimited amount of journeys for one week. This cost £15.99, and was in my Apple wallet for easy access. It definitely saved me a lot of money during my trip. The link to download is here.
Chicago City Pass
The Chicago City Pass costs £110, and includes entrance to 5 attractions. Entrance to the Shedd Aquarium and the SkyDeck are included as standard, and then you can choose the other three from the options below:
• Architecture River Tour
• Field Museum
• 360 Chicago
• Griffin Museum of Science and Industry
• Art Institute of Chicago
• Alder Planetarium
Once you purchase your card and pick your attractions, you will need to select the dates and times of your visits. These don’t all have to be done at once, and can also be rearranged. It is very flexible.
The Chicago City Pass is great value for money if you plan on visiting any of the above. Most entrance fees are between £30-£40pp, so you save about 49% if you use all five spaces. The link to purchase is here.
Now onto my top 10 things to do:
1. The Bean (obviously)
“The Bean” is the popular nickname for the Cloud Gate sculpture by Anish Kapoor, located in Chicago’s Millennium Park. The 110-ton, mirror-polished stainless steel sculpture was completed in 2006 and reflects the city’s skyline and sky, with a 12-foot-high arch inviting visitors to explore its concave interior. It’s a major icon of Chicago and one of the largest of its kind in the world.

It is free to visit, and you can walk underneath it and take photos.


2. A Sports Event
I’m big on Ice Hockey, so a Blackhawks game was my first choice, but Chicago also has the Bears if you like football, the Cubs if you like baseball, and the Bulls if you like Basketball. it also depends what season your visit falls in.
The venues in the States are much larger than what I’m used to, so it was pretty surreal seeing the volume of people watching the game.



I also of course had to visit the Hockey Barn for drinks.




3. Shedd Aquarium
The Shedd Aquarium, with its impressive entrance facing Lake Michigan, attracts millions of visitors each year. It is a popular destination for both locals and tourists. Its commitment to education, conservation, and research contributes to its reputation as a leader in the field of aquatic sciences.




The aquarium houses over 32,000 animals, from belugas, stingrays, sea otters, sea stars and many more. They also have dolphin shows, where you can watch Pacific white-sided dolphins performing acrobatics, and this is included with your ticket.
Entrance to the Shedd Aquarium is included in the Chicago Pass, but if you don’t opt for this, it’s £36 per person.
4. Walking tour
While my friends were working, I booked a walking tour of the city with a local guide. His name was Dave, and he gave me an amazing tour of the city. We started at the Chicago Theatre, and visited Macey’s, the library, the athletics association, and the board of trade building. We also stopped at a few famous food joints. This took up most of the day, and it gave me a great insight into the history of Chicago.





If you’d also like to do a food/walking tour with Dave, here is the link to book.
5. A River Architecture Cruise
Despite the November cold, one of my favorite activities was the architecture cruise along the Chicago River. The boat I used to was the Star of Chicago, and was equipped with a bar and a bathroom, and the tour takes ninety minutes.

Our guide gave us a commentary of all the notable buildings along the Riverwalk, including their historic significance and the inspiration behind them. It was very informative, and I’d love to do it again in slightly better weather.




6. Local Food
Chicago is famous for many different food items, and I made it my mission to try them all.
First off, there is the iconic Chicago pizza. Deep dish, with cheese underneath the sauce. It is more like a pie than a traditional pizza, but is a must try in Chicago. It wasn’t my personal favourite, but I’m glad I gave it a go.

The Chicago hot dog is another great option. This dish was born during the Great Depression, when venders offered a cheap all-in-one meal. This is a beef frankfurter in a seeded bun, topped with yellow mustard, pickle relish, white onions, tomatoes, a dill pickle, sport peppers and celery salt.

The Chicago italian beef sandwich from Luke’s is also very iconic. This is thinly sliced beef served in a soft roll, with gravy, cheese and peppers.

Garrets Popcorn is well rebound for its ‘Garret mix’ which is a combination of toffee and cheese popcorn flavours. It sounds gross, but it is my favourite popcorn to this day!

Chicago is also home to McDonald’s headquarters, so they have a branch there that is dubbed as “Worldwide McDonald’s”, where they have a rotation of menu items from around the world. Unluckily for me, most of the items when I visited were European and I had tried them, but I did manage to get some spicy pepper and garlic chicken nuggets from Japan, and some shaker fries from Canada. The other items were also delicious, but I had tried them on previous travels.


7. SkyDeck
The SkyDeck is located at the top of the Willis Tower, the tallest building in the city.
Before heading to the SkyDeck itself, there is a small exhibit of different parts of Chicago, including a giant pizza and hot dog, and a
You have to take a lift up to the top, which takes just under one minute, and then you are free to admire the views and step out onto the glass platforms overlooking the street. There is a photo opportunity here that you can buy from the gift shop.
I visited just as the sun was setting, so got an incredible view of the Chicago skyline at golden hour.
As well as the SkyDeck in the Willis Tower, this is also the 360 Chicago. This one has the platforms that you stand on and they tilt forward, and also has a bar. This one was further away than where I needed to be next, so I didn’t try it, but if you have more time, it’s another option.
8. Starbucks Reserve
The Starbucks Reserve in Chicago isn’t just a coffee shop, it’s an experience, perfect for coffee lovers and tourists alike. Spanning over four floors and taking up 35,000 square feet, it is the largest Starbucks in the world.

The menu here includes a wide range of exclusive beverages, including cocktails, small-lot coffees and gourmet food, but it isn’t just a normal Starbucks, it is a multi-sensory experience with so much going on.
If you have a spare hour and enjoy your coffee, I would recommend booking a coffee lab or mixology workshop. They offer lots of experiences to educate people on the science of coffee.
And who doesn’t love a coffee flight?

9. Museums
Chicago has no shortage of museums, with themes to suit all ages. Some of the most popular include
• The Art Institute
• The Field Museum
• Griffin Museum of Science and Industry
• Museum of Illusions
• Chicago History Museum
• Chicago Sports Museum
On my trip, I visited Sue the dinosaur at the Field Museum, and spent a morning at the Chicago History Museum. Both were excellent, and very educational. The Field Museum is very reminiscent of the Museum of Natural History in London.






10. A Comedy Show
The comedy scene in Chicago is huge. Chicago is the comedy capital of the USA, and people travel from all over the world to train at their theatres.
I watched a show called Something Unexpected at the Laugh Factory, and as I’d never been to a comedy show before, I was unsure what to expect. I did however thoroughly enjoy myself, and attend them at home when I can. (I do know the comedian in the photo, so this was allowed).


Chicago is a great city, brimming with things to do and see, and tasty food to try. If you ever find yourself in the States, Chicago is definitely somewhere to consider visiting.
If you are planning a trip, I hope you find this blog helpful!
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