Chicago’s Highlights Day Trip

There are so many things to see and experience in Chicago, but if you are in the city only for a short time and would like to focus on things that are unique to Chicago, this is the itinerary for you.

Among one of the things Chicago is well known for is its magnificent, unusual architecture, with the different skyscrapers’ designs and unique features, due to the constraints from lying on the river, Lake Michigan, and the strong winds from its direction.

This eclectic collection that creates a fascinating urban landscape can be seen from the ground when walking around the downtown area, while on a boat on the Chicago River, or from above, either through the glass box on the 104th floor of Willis Tower (which was, till 1998, the tallest building in the world), or from 360 Chicago Observatory deck (used to be called the Hancock tower).

Download a pdf format map.

This Itinerary will focus on several of the Must-See places in the Chicago downtown area. Starting at the Millennium Park and heading north till 360 Chicago.

Recommended time: This tour is mostly outdoors, so comfortable weather to wander outside is required to enjoy it. It can be fun during the winter, or while it’s drizzling, just add more indoor stops. There are several options along the route, like cafes, restaurants, and shops, as an escape if the weather gets too extreme, or just for a break.

Duration: 4-6 hours.

Arriving at the starting point: The closest train station to Millennium Park is Washington/Wabash. There are also several bus options.

Guided Tour options: We suggest to add a guided tour to this day trip in order to learn more about the city’s history, how it got developed, its relationship with its rivers and Michigan Lake. Click here to view options of walking guided tours as well as a boat guided tour on the Chicago River.

1. The Cloud Gate at Millennium Park
201 E Randolph St, Chicago, IL 60602.

We will start this day trip in one of Chicago’s top touristic attractions and the city’s iconic symbols, which is an outdoor statue called The Cloud Gate. Its nickname “the bean” was assigned to it due to its shape. The statue is made of polished stainless steel creating a reflection of the skyscraper and the people nearby.

Walk around the Millennium Park to check out more exterior art exhibitions.
During the spring and summer seasons, the park hosts music festivals, public dance and yoga classes, and many more different activities.

Connected to the Millennium Park is Maggie Daley Park, named after the former First Lady of Chicago.
The park has “Skating Ribbon”, magical “Play Garden”, rock climbing and bouldering walls, 18-hole miniature golf course, and picnic areas.

2. McCormick Bridgehouse & Chicago River Museum and DuSable Bridge
333 Michigan Avenue, Chicago, IL 60601.

Walking along the Chicago River is a great angle to admire it from, as well as the skyscraper on its shores.

Before crossing to the next bank, you can enjoy walking east/ west along the Chicago River-walk.
Another option is to pay a visit to the McCormick Bridgehouse & Chicago River Museum where you can learn about the bridge’s history and structure, as well as getting a glimpse of the view from one of the bridge’s top windows.

* Chicago’s First Lady Cruises
112 E Wacker Dr, Chicago, IL 60601.

If you wish to take a cruise tour on the Chicago River, this woman-owned company departure location is close to the DuSable Bridge. The cruise is a wonderful way to see the city, learn about it while sitting (and get a nice break from walking).

3. Magnificent Mile
435 N Michigan Ave, Chicago, IL 60611.

Cross the DuSable Bridge, and you are entering North Michigan Avenue, which is famously known as the Magnificent Mile, a beautiful street with great window watching and shopping options.

Notice the height and the design of the skyscrapers; most were built in the first quarter of the 20th century. Close to the bridge is the Wrigley Building with its Clock Tower and the Tribune Tower (435 N Michigan Ave.), a neo-Gothic skyscraper that used to be the home of the famous Chicago Tribune till 2018 (Chicago Tribune’s first female editor was Ann Marie Lipinski, in 2001).

4. The Historic Water Tower and the City Gallery
806 Michigan Avenue, Chicago Tower.

Towards the last part of the Magnificent Mile do not miss the Historic Water Tower and the City Gallery on its lower level. It is the second-oldest water tower in the United States, one of the few buildings which survived the Great Chicago Fire of 1871, and is considered to be one of the city’s most famous landmarks. It was designed in the 19th century by one of the city’s most bountiful architects, William W. Boyington.

5. 360 Chicago Observatory in the John Hancock building
875 N Michigan Avenue, 94th Floor, Chicago, IL 60611.

This skyscraper was opened in 1968, and back then, it was the second-tallest building in the world and the tallest outside New York City. The 360 Chicago is an Observatory in the building’s 94th floor, and after a long day of walking you can enjoy a combined Cocktail & View ticket at Bar 94.
Another lookout option is the Signature Lounge on the 96th floor which offers cocktails and food while enjoying the views of the city.
During this day trip, you have admired the giant skyscrapers from the ground; these observatory points allow you the option to admire this beautiful city, but this time, from the top.

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