We recently spent a weekend in Chicago as part of a three week trip across the US. It was our first stop after a 9 hour flight from Zurich and our first taste of the US. When I told some of my friends we were planning to visit Chicago we were met with inquisitive looks and questions like “what on earth is there to do in Chicago”? Well I have to say we absolutely loved it, and two days really was not enough. Chicago is a city full of incredible architecture, world class museums, and a pretty awesome take on pizza. It really is a city worth exploring. If you are short on time like us, follow our guide on how to spend two days in Chicago. 

Day 1

Do the Riverwalk

We recommend starting your adventures in Chicago by doing the Riverwalk. It is a 1.25 mile long promenade filled with outdoor bars and cafes, and as you’d expect it goes right along the river. The adventurous among you can rent bikes or kayaks, whilst the rest of us can just walk along taking in what has to be one of the most beautiful parts of the city.

Take an Architecture Cruise

One of the first things in Chicago that draws you in, has to be the buildings. I know New York or any other big city has tall skyscrapers, but there is something much more intriguing and beautiful about Chicago. You look up and you really want to know more. Luckily there is a cruise that can answer all your burning architecture questions. We went with First Lady cruises, located along the promenade.  It cost around $43 plus tax, which might sound steep but we felt it was worth it. The tour lasts around 1.5 hours, and you get an in depth guide into the buildings that make Chicago what it is today.

Explore Navy Pier

One of Chicago’s most popular attractions has to be Navy Pier. If you follow the signs across the Riverwalk you will start to lose sight of the looming skyscrapers and reach Lake Michigan. The real appeal of Navy Pier is that there is a little something for everyone. From rides, to restaurants, to the Shakespeare Theatre, there is an eclectic mix of activities for the whole family. There are also outdoor bars with some unreal views of the city.

Unfortunately for us, when we visited we got to see why they call it the windy city. The weather wasn’t really working in our favour, but we did not let that stop us. We sat near the water, Dave with a beer in hand, and me with a fruity cup of Sangria, as the rainclouds loomed in the distance. And despite the fact that we couldn’t put our drinks down for fear they would blow away, we had a great time gazing up at the Chicago skyline.

Visit The John Hancock Centre

One of two observation buildings in Chicago, we recommend you visit the John Hancock Centre about an hour before sunset. Be prepared for queues, unless like us you arrive on a day the ticket desk clerk called “the foggiest he had ever seen”.  So we found it pretty much deserted. We debated about whether or not to go up, but considering we were only in Chicago for a short time decided to go for it. It’s $25 to go up and that does include a cocktail from the bar (tickets are slightly cheaper if you want to skip the drink). There are quite a few places to sit and enjoy the view, or in our case fog, whilst sipping a drink and looking out from the 94th floor.

Day 2

Admire The Views From The Willis Tower

We visited the Willis Tower first thing in the morning and did not regret it. The tower opens at 10am so if you get there at least 30 mins before this, you have a chance of being one of the first groups up the tower for the day. For us it was fantastic because we got to spend a bit of time on the clear observation boxes before the crowds arrived.

Take Selfies In Millennium Park

There is nothing that says Chicago more than taking a reflection selfie with the Bean in Millenium Park (at least according to our Instagram feed anyway). Designed by Anish Kapoor this 110 ton silver sculpture perfectly reflects the Chicago skyline, and seems to be a real favourite amongst visitors to the city. Don’t forget about the rest of the park though. It is like a small garden oasis in the middle of the bustling city.

The park fountains are also worth a visit. There are two 50 ft towers  with video footage of different faces. Apparently these are all faces of native Chicagoans, and they pucker up and spit water every so often. We found a lot of families gathered around here, with kids splashing around in the water trying to keep cool.

Get Cultural At The Art Institute of Chicago

A short walk from Millennium Park and you will find yourself at the Art Institute of Chicago. Our Lonely Planet guide lists this as the top thing to do in Chicago so it really is worth a visit. It is the second largest art museum in the country and houses collections from around the world. The highlight for me was seeing artwork by Andy Warhol, but you will also see works by Picasso and van Gogh.

Visit A Speakeasy

Exploring a city can be thirsty work, so you should head over to the Green Door Tavern for a few drinks. Chicago has a fascinating history, particularly in the prohibition era so a visit to a speakeasy is a must. The reason for the name is because in the prohibition era if a tavern door was painted green this meant the presence of a speakeasy. There are a lot of historical speakeasies in the city and some are even famed for being the hangouts of mob bosses such as Al Capone, although these tend to be located away from downtown Chicago.

Munch On Some Deep Dish Pizza

You cannot, I repeat, CANNOT leave Chicago without trying the legendary deep dish pizza. There are a number of places throughout the city that serve the famous dish so take your pick.We ate at Pizano’s and we loved it.  As the name suggests the pizza crust is quite deep allowing for a lot of cheese and fillings. It was one of our favourite meals on our trip the US, so we do recommend it.


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