Epic 3 Days in Chicago Itinerary for Architecture Lovers

We recently visited Chicago for an architectural nourishment trip. Because we are architecture lovers, we wanted to deeply explore the design side of the city. We discovered so much history and so many hidden gems, some of which are mistakenly underrated, like the Frank Lloyd Wright home and studio.

If you are planning a trip to the Windy City for the first time and want to explore its structural marvels, this 3 days in Chicago itinerary is exactly what you need. This detailed guide ensures you plan ahead, giving you valuable information so you do not waste your trip on popular things that lack value, but instead focus on the things that absolutely need to be on your radar.

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Why Chicago is an Architectural Dream

Located along the massive Great Lakes of Michigan, and famously known as the Windy City due to the incredible wind experienced during our stay, layers are a must. Chicago is actually the birthplace of the skyscraper. The fire date was in 1871, which destroyed the city because most of the buildings were made out of wood. When they rebuilt the city, they started building tall.

During this reconstruction era, they also shifted the river to avoid contamination from flowing into Lake Michigan. This trip was completely tailored to explore and learn everything about this incredible architectural history. We spent three full days here, and we truly feel we could stay another day.

The Ultimate 3 Days in Chicago Itinerary

Day 1: Downtown Marvels and Fine Art

1. Millennium Park

This park is the lung of Chicago, boasting around 25 acres of green space. There are several things to explore in this park.

• Cloud Gate: The park is home to the famous bean, which is a metal legume sculpture designed by Anish Kapoor. It was inspired by liquid mercury and is one of the most photographed spots in the city. A visit to the Cloud Gate is a must, and be prepared to take photos and walk around and underneath the bean. Right next door is the McCormick Tribune Plaza, which hosts an ice skating rink during winter right in front of the bean.
• Jay Pritzker Pavilion: The park is also home to this pavilion designed by Frank Gehry, the architect who also designed the famous Guggenheim Museum Bilbao. This pavilion was designed to provide live performances. Check the calendar for live concerts on the great lawn.
• Crown Fountain: An interesting fountain designed by Jaume Plensa with two glass towers and a reflecting pool in the middle. It features a screen with water flowing out, giving the illusion of water coming from the outside of their mouths. During our visit, it was super cold, and the fountain water was not working, but the screen reflecting the faces of different individuals was visible. In the warm season, the fountain is operated, and children use it to get a splash of water.

2. The Art Institute of Chicago

• Hours: Open Wednesday to Monday from 11 AM to 5 PM (closed on Tuesday).
• Tickets: Starting from $32, access included with Chicago CityPASS.

This is the second largest museum in the USA, where you will find incredible art from Picasso, Monet, and Van Gogh. The museum is huge, and if you visit, expect to spend at least two hours. If you want to explore it in more detail, you can join the free tours offered at 1 PM and 3 PM. Click here to check the free tour dates.

During our visit, we wanted to make sure we hit the highlight art like American Gothic, Art of the Americas, Salvador Dali, Picasso, Van Gogh, and Le Corbusier. To plan your visit better, take a sneak peek at the museum map here.

3. The Chicago Theatre

• Hours: Guided tours typically run Friday to Sunday (check tour availability here).
• Tickets: Tour tickets typically start at $32.

This is an iconic destination. Interestingly, this building was the first large, lavish movie palace and initially was built as a movie theater and later became a performance theater. You can find several live performances and stand-up comedy in the theater.

You can see the calendar options here. Even if you decide not to visit for a tour or performance, it is really worth it to see the beautiful facade with the neo-baroque style from the outside with the colorful Chicago theater sign.

Day 2: Historic Homes, Science, and Sky High Views

4. Frank Lloyd Wright Home and Studio

• Hours: Open daily from 9:30 AM to 5 PM.
• Tickets: Admission starts at $24. You need to book in advance here, it is a must.

To get to the Frank Lloyd Wright Home and Studio, we decided to use a rideshare. While you can take the CTA Green Line train, we don’t recommend it because it takes quite a bit of time and still requires about a 15-minute walk from the station. However, if you prefer to take the train, you can check the train lines here.

A visit to the house offers two tours:

• Interior tour combined with an outdoor historic neighborhood audio tour,
• Interior tour alone.

We opted for the interior tour, which is a one hour guided tour discovering the Frank Lloyd Wright first home and studio, in which some of his famous architectural visions were created and inspired.

In the house, you will learn about his life and his professional growth. The house and studio are furnished with several original pieces of furniture, some of which were designed by Frank Lloyd Wright himself.

5. Griffin Museum of Science and Industry

• Hours: Open daily from 9:30 AM to 4 PM. Tickets:
• Tickets start at $25, get your tickets in advance here. Access included with Chicago CityPASS.

The museum is located in a building built for the 1893 World’s Columbian Exposition. This museum brings to life an interaction of science with the public, so be ready to learn and play with the different science projects inside. This is one of the museums that is not necessarily targeting young people, it is a place for adults to enjoy.

One of the coolest parts is seeing a scale model of the city of Chicago with moving trains and lighting, which gives you a total vibe of the city. Note that there is a hidden wall where you find how the streets of Chicago looked in the past around 1900.

It covers science, space exploration, and engineering, and it also has a big submarine from Germany from World War 2 you can get inside. But you need to book your ticket for this experience in advance because they sell out super fast.

6. Willis Tower

• Hours: Open daily from 9 AM to 10 PM.
• Tickets: Tickets start at $47. Also included with Chicago CityPASS. Booking in advance is a must.

The Willis Tower is the former Sears Tower since it was the headquarters of Sears, Roebuck and Co. The experience starts with a visit to an interactive museum that goes over the culture, history, and architecture.

This is a popular attraction, and tickets in advance are a must, not an option, as your visit is organized based on your ticket slot time. You can get your skip-the-line tickets to the Willis Tower here.

Once you are done with the interactive musem, you will get into the elevator to the 103rd floor, where you can also spot the spot in which the Ferris Bueller’s Day Off movie was filmed. It ends with incredible access to a glass ledge 1.5 inches thick which extends outside the building, giving you an incredible city view. You will be literally stepping on top of a cantilever glass box.

Interestingly, this transparent addition was actually created because visitors kept leaving forehead prints on the windows while trying to look straight down at the street below, often while mimicking that famous movie scene. The best time to visit is at sunset to have a view of the city when the buildings and streets illuminate the city.

Note: There is another popular city sky view in the Hancock building where the glass tilts 30 degrees outside the building, and you lay down looking at the city from the 94th floor. We could not visit this one, but several friends who have visited said that it is a unique thrill experience in a positive way. You can get your skip-the-line tickets here.

Day 3: Fossils, Bus Tours, and River Views

7. Field Museum

• Hours: Open daily from 9 AM to 5 PM. Tickets:
• Tickets starting at $29, book tickets in advance here. If you are an Illinois resident, you can get free tickets here on Wednesdays.

The Field Museum focuses on natural history and biodiversity. You will find exhibits on some of the most famous ancient civilizations, large dinosaur fossils, and natural history.

If prehistory is something you like, this is a must. The field museum is where you can find Sue, the Tyrannosaurus rex fossil, which is the most complete fossil ever discovered in 1990 in South Dakota.

8. Chicago Architecture Center

• Hours: Open Sunday to Thursday from 10 AM to 5 PM and Friday to Saturday from 10 AM to 7 PM.
• Tickets: Tickets starting at $15.

The Chicago Architecture Center started as an architecture foundation to save the historic Glessner House in Chicago, designed by Henry Hobson Richardson. The massive scale model of the city of Chicago is on the first floor behind the museum store. On the second floor, you will find images of different size scale models of individual iconic buildings in Chicago like the Hancock and Marina City buildings.

The museum is small but very educational. We decided to book a bus tour where we visited several landmarks of Chicago like Crown Hall, The Rookery building, Al Capone’s historic Chicago home, and others. You can book your tickets for the bus tour here. If you decide to do a bus tour or a walking tour, you will get free access to the museum.

9. Robie House

• Hours: Open Thursday to Monday from 9:30 AM to 4 PM.
• Tickets: Tickets starting at $24, book in advance here.

This is another Frank Lloyd Wright masterpiece. We visited it as part of the bus tour of the Chicago Architecture Center. Unfortunately, during our visit it was closed due to renovations, but we were able to get a sneak peek of the interior through the windows and a better view of the remarkable facade of this house with the bricks placed with different mortar colors, which gives this extensive horizontal elongation and gives the illusion of being an elongated horizontal piece.

The visit has three options. The interior tour combined with the audio outdoor tour, the interior tour with a modern architecture focus, and the interior in-depth tour, which covers in depth the Frank Lloyd Wright architecture style and details about the house design and furnishing. If you are interested in the in-depth tour, you must book in advance because this tour is limited to 10 guests.

10. Chicago Riverwalk

The Riverwalk is packed with shops, stores, restaurants, bars, and cafes. A walk gives you a perfect view of the skyscrapers along the river.

We decided to walk it, but if you want to, there is a boat that sails the river and gives an Architecture boat tour. It is an open-roof river boat that takes you through the history of Chicago architecture.

How to Move Around

We decided not to rent a car, and it was the best decision ever. We don’t recommend renting a car because parking is expensive and in certain areas limited. We walked late at night, and the city is very pedestrian, and we never felt unsafe.

We took a rideshare to our hotel and spent most of our trip either walking or using rideshare apps. However, the ‘L’ elevated rail system is another excellent option to get around. Conveniently, the Blue Line train will take you directly to and from O’Hare Airport. If you plan to use the train, you can purchase a Ventra card at any rail station. Click here to check the different fares and view the train map.

Best Time to Visit

We visited in March, and it was cold and rainy, still we enjoyed our time visiting it. If you visit, we highly encourage bringing layers. Temperatures are super cold from October to March, we recommend coats, and for April to May, layers, and June to September, light clothing. The wind feels more intense due to proximity to Lake Michigan.

Where to Stay in Chicago

There are several nice neighborhoods to stay in Chicago, but for a first-time visitor, the most convenient area is downtown, which is close to the must-visit destinations. Another option is River North. We decided to stay at Langham Chicago, which is two blocks from downtown and by the river.

This is a Michelin Key hotel with incredible luxury amenities. If you want to know about our experience staying in this hotel, check out our full Langham Chicago Review here. If you are doing quick research on where to stay, check out these other alternatives for luxury, mid range, and on budget hotels here.