Top Things to Do in Chicago (2 day itinerary)

Chicago, a bustling city full of culture, beautiful architecture and tasty deep pan pizza! Located on the shores of lake Michigan, Chicago is the third most populous city in the USA. If you are planning a trip to the windy city then keep reading to find out the top things to do in Chicago, including where to find the best deep pan pizza!

Where I stayed: Acme Hotel

1) Go up the Skydeck

If you’re coming to Chicago then you need to go up either the Willis or Hancock Tower for amazing views of the city skyline!

The skydeck is situated on the 103rd floor of the Willis Tower (formally Sears Tower) and offers panoramic views of the city as well as the unique opportunity to stand in a glass box 1353 feet above the city!

Tickets cost €25 or it’s included in the city pass!

Best time to go : I went 40 minutes before sunset to enjoy the city during golden hour, as well as at night. Usually I would go early to take pictures with no one around but at the sky deck you have to queue to go in a glass box which means you have it all to yourself for 60 seconds (and you can queue as many times as you like)! If you’re going during a busier season like in the summer holidays I would recommend going for opening so you don’t have to queue too long.

skydeck Chicago

2) Chicago Architecture Boat Tour

Chicago has some super interesting buildings of completely different architectural styles.  It is home to the second highest building in the Western Hemisphere as well as the tallest building in the world designed by a woman!

Learn more about the architecture and history of Chicago whilst cruising along the river with Shoreline Sightseeing. The tour lasts 75 minutes and they have boats leaving throughout the day from both Michigan pier and Navy Pier.


3) Cloud Gate (the Bean) and Millennium Park

Have you even BEAN to Chicago if you don’t check out your reflection in the Cloud Gate at Millennium park?! Make sure you walk underneath it! Go at sunrise to catch the sun directly below the bean.

Make sure you walk around and explore the rest of Millennium Park including the Crown Fountain.


4) Try a Deep Dish Chicago Pizza

You can’t come to Chicago and not try a deep dish pizza! It would be like going to France and not having a croissant!

There are quite a few places offering the Deep Dish with my favourite being Gino’s East. Small deep dish pizzas start from $17 (perfect for 2 people as they are super heavy) and the interior is super rustic and cool (PLUS Leonardo DiCaprios been there!).

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5) Art institute of Chicago

Whether it’s to escape a rainy day or just to educate yourself on American art, the Art Institute of Chicago is a great place to spend a couple of hours. Especially if you’re interested in impressionist paintings.

Tickets cost €25 or it’s included in the city pass!

Best time to go : Go for opening at 10:30am.


6) 360 observation deck

The 360 observation deck, located up the Hancock Tower offers 360 views over Chicago. The building is located closer to the lake so it has (in my opinion) better views than the Sky Deck. However isn’t doesn’t have the fun photo opportunity of the glass deck. You can however pay an extra $8 to be ’tilted’ over the city.

Tickets cost €22 or it’s included in the city pass!

7) Watch a Chicago Cubs Baseball Game at the Wrigley Field

During the summer months you can catch a Chicago Cubs Baseball Game at the Wrigley Field. Baseball is a huge part of American culture and the atmosphere as a game is just insane!


8) Go to the beach

Chicago has a number of beaches which not only offer you the chance to swim in the beautiful Lake Michigan (the second largest of the Great Lakes) but also gives you a beautiful view of the Chicago city skyline!

Best time to go : Go to North Avenue Beach at sunset to watch the buildings light up!

Chicago beach lake michigan

9) Chicago Riverside walk

Don’t miss out on the riverside walk, it’s a great way to explore the city and also a good spot if you want to enjoy a cheap lunch outside!


10) Enjoy some jazz at the Green Hill

In the 1920s, Chicago gangsters like Al Capone were known to frequent the Green Mill, but ever since Prohibition, the club has garnered a reputation for hosting live jazz. They have a variety of performers including B-3 organ players, jazz vocalists and classic big bands.


11) Walk along the Magnificent Mile

The Magnificent Mile is Chicago’s premier commercial district located along one road that runs through the centre of Chicago. The street is home to shops, luxe fashion outlets, cool restaurants and posh hotels. Walk down the street and admire a wide range of architectural styles such as Parisian, Gothic, Neoclassical, Art Deco, Mid-20th Century Modern, and 21st-Century Contemporary.

12) Buckingham Fountain

Once you’ve visited the Millennium Park make sure you also check out Buckingham Fountain, one of the biggest fountains in the US!


13) Navy pier

I have included the Navy Pier in my list of things to do however it definitely wasn’t my favourite thing! It gives you a nice view of the lake and the city but personally I prefer the views at North Avenue Beach.

If you looking to have a drink or ice cream with a view then it’s a good place to come but be prepared to pay tourist prices.


If you only have 2 days in Chicago then I would suggest the following itinerary:

Day 1:

  • Start your day on the Shoreline Sightseeing Architecture Boat Tour (75 minutes)
  • Grab lunch and find a spot somewhere along the riverside walk.
  • Walk to Millennium park to see the bean and crown fountain before walking down to the Buckingham Fountain and along the Michigan River to the Navy Pier for an ice cream.
  • Watch the sunset from one of the tallest buildings in the western hemisphere, the sky deck
  • Tuck in to a deep dish pizza at Gino’s East.

Day 2:

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