One week in Chicago is the perfect amount of time to explore and enjoy everything that this city has to offer while not having to rush from one place to another. This itinerary for a week in Chicago (6 full days and 2 half days) is the perfect way to explore the wind city at your own pace.
The first time I visited Chicago, I was 13 years old and I was spending 4 weeks with an exchange family in Michigan so that I could learn and improve my English. One of the activities that this exchange program included was a two-day trip to visit. The only thing I remember from that trip was visiting the Navy Pier and going up to the Willis Tower (the Sears Tower at that time). So let’s just say Chicago didn’t make an impression on teenager me.
I returned to Chicago in September 2022 to visit with my parents and visited it for one week. This time around, I loved this city and if I might even be so bold as to say it, I liked it even better than New York! Don’t get me wrong, New York is an amazing city but there was something about Chicago that completely won me over.
INTERESTING FACTS ABOUT Chicago
Before we start with my one week in Chicago itinerary, here are some interesting facts about the city of Chicago.
- Chicago’s most popular nickname is The Windy City but it is actually not the windiest city in America.
- It is the third largest city in the US and it has a total of 77 neighborhoods.
- The Great Chicago Fire of 1871 burnt down a third of the city. However, a few buildings survived the fire like the Chicago Water Tower and Pumping Station.
- Following the Great Fire, an architectural boom happened in the city which led to the origin of Modern Architecture.
- Chicago has a total of 600 parks and it is filled with green spaces. Actually, Chicago’s motto is “urbs in horto” which translate into English as a city in the garden.
- Chicago’s Downtown neighborhood is known as “The Loop” due to the encircled area of the “L” elevated train.
- The city of Chicago has two big bodies of water, Lake Michigan and the Chicago River. Speaking of the Chicago River, did you know that it flows backwards? Instead of ending in Lake Michigan, it empties in the Mississippi river.
- There are over 60 museums in Chicago!
ITINERARY FOR ONE WEEK IN CHICAGO
When looking at this itinerary, there are two factors to consider:
- Our itinerary in Chicago got a bit influenced by the weather. The first 2 days were quite rainy and cold so we had to adapt our visits accordingly.
- In addition, on this trip, I was traveling with my parents who despite being quite active for their age, they like to travel at a slower pace. We often returned to our apartment for lunch and rest and then continued our visits afterwards.
Map with Chicago Itineary
Here you can find the map with all the spots we visited in Chicago. Each day is marked with a different color to help group the activities by days.
DAY 1: Fly to Chicago and survive Jet Lag
The first day of our trip was mainly spent traveling to Chicago. I got a direct flight between Brussels to Chicago which was very convenient. The flight was approximately nine hours that I spent eating, looking out the window, and watching some movies.
I landed in Chicago and after going through immigration and meeting my parents (they flew directly from Madrid to Chicago), we got a Lyft to the apartment we had rented for the week. The apartment was near Hyde Park in South Chicago and I could not recommend it more!
Apartment recommendation: Historic HP 2 BR with Fast Transit to UChicago & Downtown.
After settling into the apartment, we were all really tired so and jet-lagged. We basically spent the rest of the day doing some grocery shopping in a nearby supermarket and finding a place where we could buy the Ventra Cards to have unlimited public transport for a week.
DAY 2: Art Institute of Chicago
Stop 1: Art Institute of Chicago
Our first morning in Chicago was really rainy! Because of this, we decided to visit the Art Institute of Chicago.
The Art Institute of Chicago has over 300,000 art pieces from all over the world and different time periods. In addition, there are always temporary exhibitions available. This makes it the perfect place to visit no matter what sort of art you like.
Among the most famous pieces in this museum are Vincent Van Gogh’s The Bedroom, Katsushika Hokusai’s The Great Wave, American Gothic by Grant Wood, Renoir’s Two Sisters (on a terrace), etc. I could keep on going for a long time.
We spent more or less 4 hours admiring its many masterpieces! And we could have spent more, but it was getting late and we were quite hungry.
Good to know: If you are planning to visit the museum, it is interesting to know the following things:
- The Art Institute of Chicago only opens its doors to the public at 11 am. From 10 am – 11 am, it is only open to people with a membership.
- You can buy the tickets at the museum. However, if you want to ensure ticket availability, it is better to buy them online in advance.
- The ticket is valid for the whole day. This means you can visit for a while, exit to get some food and come back later.
- For more information about opening days, ticket prices, and temporary exhibitions, visit the official site: https://www.artic.edu/
Stop 2: Lunch at Shake Shack
After the museum, it was still pouring down with rain so we searched for the nearest Shake Shack to have lunch. Shake Shack is a restaurant chain that can be found all over the US. However, in my own opinion, they have really good burgers and fries. I tried it for the first time during my trip to Washington DC and I really liked them. I knew that as soon as I was back in the US I was going to find one again.
In addition, you can’t visit the US and not have fast food at least once!
Stop 3: Walking along Lake Michigan
Once we were done with lunch, it was still raining so much that it was impossible to do anything else. We decided to return to the apartment to wait for the rain to pass.
At 5 pm, it finally started to clear out. I did some research on Google and discovered that Promontory Point was only a 10-minute walk from the apartment. From here, you could get really nice views of the Chicago Skyline and the Museum of Science and Industry. From here, we had a nice walk along Lake Michigan until it got dark.
DAY 3: Millenium Park and The Magnificent Mile
Stop 1: Cloud Gate (Millennium Park)
We began the day visiting Cloud Gate in Millennium Park, also known as The Bean for its shape. Cloud Gate is a public sculpture by the artist Anish Kapoor. It is made out of 168 stainless steel plates welded together and polished. It is supposed to be inspired by liquid mercury.
The sculpture reflects people and the city skyline, so it is a very photogenic place. We arrived at approximately 10 am and quite a few people were there. However, if you have patience and wait, getting a few decent photos is always possible.
Stop 2: Crown Fountain (Millenium Park)
After taking lots of photos at The Bean, we visited another famous landmark within Millennium Park, the Crown Fountain. This is not just a regular fountain but a piece of art by the Spanish artist Jaume Plensa.
The fountain consists of two glass block towers, on each side of a shallow reflecting pool, that project images of the faces of people from Chicago from a wide social spectrum. It is an analogy to the gargoyles that were carved in fountains in the past to have water come out of their mouths.
The face images are visible all year round. However, the water features only work between mid-spring to mid-autumn.
In contrast to Cloud Gate, there were hardly any people here so we were able to spend all the time we wanted admiring the fountain. We also got to take many photos and videos while playing with the reflections in the water.
Stop 3: Chicago Cultural Center
Our next stop of the day was the Chicago Cultural Center which is famous for having a beautiful dome made of Tiffany Glass. The dome is designed to resemble fish scales and in the center of the dome, we can find the symbols of the different zodiac signs.
However, this is not the only remarkable thing about this center. Its halls and stairways are covered in beautiful marble, polished brass, and excellent woodwork that make it an architectural showplace.
The Chicago Cultural Center is open daily between 10:00 to 15:00 (except on bank holidays) and can be visited for free. In addition, there are also free tours every Thursday and Friday at 13:15. The tours are first come, first serve and are limited to 25 people.
Stop 4: Giordano's Deep Dish Pizza
At this point, it was already lunch time so we decided to try the famous Chicago Deep Dish Pizza. This Chicago-style pizza is called this way due to its cooking style. It is baked in a deep pan which gives the pizza its characteristically high edge. This allows for insane amounts of cheese and chunky tomato sauce.
We decided to try it at Giordano’s restaurant, which was the nearby restaurant with the best reviews on Google. The pizza was really good and tasty.
Good to know: If you want to try Chicago Deep Dish Pizza, knowing the following two things will become handy.
- Chicago Deep Dish Pizza takes some time to be cooked. So be prepared to wait a little bit for pizza to be served.
- This kind of pizza is quite heavy, so don’t go crazy ordering too much food. We ordered a medium pizza for 3 people and we could not even finish it. We had to take part of it to go.
Stop 5: DuSable Bridge
After lunch, we continued following Michigan Avenue towards the north until we reached DuSable Bridge. This bridge is a double-deck bridge that bascules. It allows Michigan Avenue to extend further north of the Chicago River. The bridge was first named Michigan Avenue Bridge but it was renamed DuSable Bridge in 2010 after Jean Baptiste Point du Sable, Chicago’s first permanent resident.
From the bridge, you can get magnificent views of the Chicago River and the many skyscrapers surrounding it. Among the most famous are the Wrigley Building, the Trump Tower, the Tribune Tower, etc.
We spent a really long time admiring the scenery and all the different buildings.
Stop 6: The Magnificent Mile
We finished our day by walking along North Michigan Avenue, also known as The Magnificent Mile. This avenue is full of shops so it’s the place to go if you want to do some shopping.
At the end of the street, you will find as well a few additional landmarks such as the John Hancock Center and the Chicago Water Tower, one of the few buildings that survived the Great Chicago Fire.
DAY 4: Navy Pier, Architecture River Tour and The Loop
Stop 1: Navy Pier
We began our 4th day in Chicago by visiting the Navy Pier. We were there quite early in the morning, so nothing was really open yet. However, it was perfect to have a walk along the pier and enjoy the views of Chicago.
Chicago’s Navy Pier is a pier that is full of attractions, places to eat, exhibitions, and public events. It is the perfect place to go with friends and have some fun while trying some delicious food in a cool and relaxed atmosphere.
Good to know: If you want to experience the Navy Pier with a more lively atmosphere, then it’s better to visit in the afternoon.
Stop 2: Museum of Contemporary Art
Our second stop of the day was visiting the Museum of Contemporary Art. The MCA is an innovative center of contemporary art where visitors can experience the work and ideas of living artists. It is also a way of understanding the historical, social, and cultural context of the art of our time.
If you want to visit this museum, check out their official site for ticket prices and opening hours: https://visit.mcachicago.org/
Stop 3: Chicago Architecture River Tour & Chicago Riverwalk
After lunch, the weather was fantastic so we decided to do the Chicago Architecture River Tour. This is a 1.5h cruise that takes you along the Chicago river while the guide explains to you very interesting information about the different Chicago buildings, how the city was reconstructed after the Great Chicago Fire, and much more.
This boat cruise was one of the highlights of the trip and a must-do during your visit to Chicago. During the activity, you will learn about the different architectonic styles of the buildings as well as how skyscrapers are built in order to resist the strong winds in the city. All the information given was very interesting and there is no better way to admire Chicago architecture than from the river.
If you want to do the Tour at a particular time of the day, make sure to book your tickets in advance. It is also a guaranteed way of skipping the line: Chicago Architecture Cruise
Stop 4: Chicago Theater
Once our river cruise was finished, it was time to explore a bit more Downtown Chicago or The Loop.
We began with the Chicago Theater. This theater was the first large movie palace in America and it was the flagship of the Balaban and Katz movie theater chain.
The building was built in the French Baroque style and its exterior facade is a mini replica of the Arc de Triomphe in Paris.
Today it is possible to attend music concerts in The Chicago Theater. If you want to do so, you can buy your tickets at their website.
Stop 5: Downtown Chicago
Right next to the Chicago Theater, there was a stop of the “L” train. Since we had a card with unlimited rides, we decided to get it a do a ride around the loop. Although this is just a regular train that goes above the street, it is also an experience to try in Chicago.
We got off the “L” train at La Salle/Van Buren stop and explored this area. Around here, there are several beautiful buildings that are also impressive if you are an architecture enthusiast.
- The Chicago Board of Trade Building. A 44-story art-deco skyscraper with a statue of Ceres on its top, the goddess of agriculture.
- The Rockery Building, a historic office building. At 55 meters high, it is considered to be the oldest high-rise in Chicago.
- Federal Plaza Square with the famous Red Flamingo by Alexander Calder. It is a 16m high steel statue painted in bright read to contrast with the darkness of the buildings in the square.
DAY 5: Lincoln Park, Gold Coast and The University of Chicago
Stop 1: Lincoln Park
Day 5 began by visiting Lincoln Park. Lincoln Park, is a huge park in the northern neighborhood of Chicago with the same name. This park is full of little gems like the Alfred Caldwell lily pond, the Lincoln Park Conservatory, Peggy Notebaert Nature Museum, and much more!
We spent the morning walking around and discovering the beautiful sites this park had to offer.
Stop 2: People's Gas Pavilion (The Honeycomb)
Within Lincoln Park, you can find the People’s Gas Pavilion also known as The Honeycomb Pavilion. Like its name suggests it is a small pavilion with its roof imitating a honeycomb, located near the Ulysses S Grant memorial statue.
This pavilion was designed by the renowned Chicago Architectural Firm Studio Gang led by Jeanne Gang. It is frequently rented for weddings and different events.
From here, you will be able to take really pretty photos with the Chicago skyline in the background.
Stop 3: North Avenue Beach
Right next to Lincoln Park, you can find North Avenue Beach. This beach is one of Chicago’s most popular beaches and it is the perfect place to go for a swim if you’re in Chicago on a warm summer day.
At the North Avenue Beach Pier, you will also get a really good view of the Chicago Skyline.
Stop 4: The University of Chicago
We spent the afternoon visiting the beautiful University of Chicago.
The first thing we visited was the Frederic C. Robie House which is a single-family house designed by the architect Frank Lloyd Wright. The house was built in 1910 and is a perfect example of the Prairie School, the first architectural style defined as purely American.
It is possible to visit the House and its garden by joining a guided tour. More information about opening times and tour possibilities and prices is on this website: https://www.flwright.org/tours/robie.
Unfortunately, we visited the campus on a Wednesday so we could not join one of the tours. Nevertheless, we did admire the house from the outside.
Afterwards, we spent some time wandering around the university campus. The campus looked exactly what universities look like in movies or tv series.
The University of Chicago is a private research university established in 1890. Its main campus is in the Hyde Park neighborhood of Chicago between 57th and 59th street and S Ellis Ave and S University Ave.
DAY 6: Grant Park, Museum Campus and Chicago 360
Stop 1: Cloud Gate (Millenium Park)
Day 6 was very sunny so we decided to go back to the most famous park in Chicago, Grant Park. Inside it, you can find Millenium Park and The Bean. We wanted to see it again on a sunny day. On our first visit, the weather was very gloomy. We also had a few highlights to see in this park that we had skipped due to the bad weather so we had to go nearby anyway.
It is a completely different experience seeing it on a grey day than on a sunny day, you get to play more with the reflection of the buildings in the sculpture. We spent a lot of time just looking at it and taking many photos of us and the reflection of the buildings. In addition, we got really lucky because there were also fewer people around the sculpture than the previous day.
Stop 2: Jay Pritzker Pavilion (Millenium Park)
Once we had had enough of The Bean we continued to the Jay Pritzker Pavilion designed by the architect Frank Gehry. This is an open-air concert hall where people can listen to music in the summer months.
The construction of this pavilion had a lot of controversies as there are historical height limitations on the buildings within Grant Park. To avoid these, the concert pavilion is considered as an art piece rather than a building.
Stop 3: BP Bridge
Right next to the Pritzker Pavilion, there is the BP Bridge also designed by Gehry. It is a snakelike bridge that connects Millenium Park with Maggie Daley Park. The bridge is named after the energy company after it donated 5 million dollars for its construction.
Stop 4: Buckingham Fountain (Grant Park)
Our next stop was the Clarence F. Buckingham Memorial Fountain, right in the center of Grant Park. It is one of the largest fountains in the world and it was designed to imitate one of the fountains of Versailles Palace. The fountain only operates between mid-May and October and offers water shows every hour. In the evenings these are with colored lights.
Stop 5: Agora Sculpture (Grant Park)
Our last stop within Grant Park was Agora sculpture. This is an art piece that consists of 106 headless and armless iron sculptures. It is designed by the Polish artist Magdalena Abakanowicz.
When installed, this sculpture produced mixed feelings among the citizens of Chicago. Many of them loved it and many hated it. I have to say, I was between the ones that loved it. It was a lot of fun to walk around the different sets of legs.
Stop 6: Museum Campus
From Grant Park, we got on a bus to the Museum Campus, Chicago’s main cultural, nature, and sports area. The campus includes the following sites:
- Shedd Aquarium: One of the first inland aquariums in the world with more than 100 different animal species.
- Field Museum: The Natural History Museum of Chicago with Sue, the most complete T. Rex skeleton ever found.
- Soldier Field: The Chicago Bears soccer stadium.
- Adler Planetarium: The first planetarium that ever opened in the US.
Stop 7: 360 Chicago
In the early evening, we went to the John Hancock Center, a 100-story building on the Magnificent Mile. On the top of the skyscraper, you can find 360 Chicago observation deck. As its name says, this observation deck offers 360-degree amazing views of Chicago.
There are different tickets that allow you access:
- Regular admission
- Sip & View: On top of the regular admission, it includes a choice of a drink.
- Tilt & View: Regular admission + Tilt Experience (not recommended for people scared of heights).
- Sip, Tilt & View: A combination of all of the above.
- 360 Sky Yoga Saturdays: General admission and a yoga class with an amazing view (only on Saturdays).
We stayed there for around an hour and half to watch the sunset and it was amazing. It was definitely another must-do in Chicago.
DAY 7: Skydeck Chicago and Chinatown
Stop 1: Skydeck Chicago
On our last full day in Chicago, we decided to visit the other observation deck in the city, Skydeck Chicago on top of the Willis Tower (originally the Sears Tower). The Willis Tower is a 110-story skyscraper designed by architect Bruce Graham. It opened in 1973 and it held for 25 years the title of the highest building in the world.
On top of the Willis Tower, you can find Skydeck Chicago, which also offers amazing views of the city. The ticket to Skydeck Chicago includes access to The Ledge. These are 4 cubicles completely made of glass that will make you feel you are floating. The first step to enter these cubicles was a little bit scary but I have to admit that once we were in them you forget about the height.
Visiting Skydeck during the morning gave us a completely different experience than the one we had the day before at 360 Chicago. The views were amazing and we got to see Chicago from a different perspective.
Tips for visiting Skydeck Chicago:
- Tip 1: Go as soon as it opens to ensure there are not many people there. Access to The Ledge is limited to 1 minute and one cubicle per person. However, since there were no people waiting in line, we got to spend almost 30 minutes in there and switched to all the cubicles.
- Tip 2: Book your tickets in advance to avoid having to wait in line for them. You can book your tickets on this link.
Stop 2: Union Station
After Skydeck Chicago, we walked to Union Station. This train station is really pretty (both on the outside and the inside). Union Station is also famous (or at least its stairs are) for appearing in the movie “Untouchables”. On these stairs, Eliot Ness, played by Kevin Costner, had a shoot with Al Capone’s men.
I am not a particular fan of this movie but my dad was, so we included it in our itinerary and I was glad about it. The station really surprised me and was a nice place to see. Same as everybody who visits New York goes to see Central Station, if you come to Chicago, you should include Union Station in your itinerary.
Stop 3: Michael Jordan's Statue
Our third stop of the day was to visit the statue of Michael Jordan in the United Center, the stadium of the Chicago Bulls and Blackhawks.
This statue is also known as The Spirit and it’s a bronze by Amrani. The sculpture was created after Jordan’s retirement following three consecutive NBA championships.
It was originally located in the east parking lot but in 2015, it was moved to the Atrium inside the stadium. It can be visited daily between 10am and 6pm.
Stop 4: Chinatown
We completed our day with a visit to Chinatown.
First, we visited the Nine Dragon Wall which was constructed in 2003. There is a total of three ancient Nine Dragon Walls in China. They are located in Datong, Shanxi Province, and Beijing and they are replicas of screen walls in ancient Chinese architecture. The one located in Chicago is a replica of the one in Beijing and its the only replica outside of China.
Ancient Chinese believed the number 9 to be the most prestigious number and that the dragon is the soul of all things of creation. Chinese emperors were self-acclaimed as reincarnations of dragons. For this reason, the emperors of the Ming and Qing dynasty built the Nine Dragon Walls to show off the supremacy of the imperial power.
Chinatown neighborhood in Chicago is one of the most significant concentrations of Chinese-American in the United States. This makes this area quite interesting to visit. The streets are full of authentic Chinese restaurants and buildings have Asian-style features.
We also spent some time wandering around the main streets of Chinatown, exploring the different shops and buildings.
DAY 8: Hyde Park Area & Fly Back
Stop 1: Hyde Park
We spent our last morning in Chicago visiting Hyde Park which was near our apartment. Our flight back was in the early afternoon so we still had some time to explore in the morning.
In Jackson Park, you can find the Museum of Science and Industry. This museum was formerly the Palace of Fine Arts and even if you are not planning on visiting it, the building and the area are quite beautiful.
Not far from this museum, you can also find the Garden of the Phoenix, a small but beautiful Japanese garden.
And that’s it for our one-week in Chicago itinerary. I hope you liked it and found it useful. Let me know what you thought in the comments.
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