I just spent a weekend in Chicago with some friends. Known as the Windy City, it is one of the most populated cities in the United States. Located at the southwestern tip of massive Lake Michigan in the state of Illinois, Chicago is the financial capital of the Midwest. Famous for its groundbreaking architecture as well as its cultural and educational institutions, it is also home to President Obama. Learn more about what to do in Chicago in a weekend by following my detailed itinerary!

We spent a whole weekend in Chicago, so find our itinerary below, broken out by day.

Are you ready?

For your ease of reference, you can also find all the worth sightseeing places and restaurants mentioned throughout this post in the map at the end of this page.

What to do in Chicago

Day one (Friday)

Since we arrived to Chicago in the evening, we enjoyed a walk around downtown, bordering the Chicago River and admiring the impressive buildings of this city. Both by day and by night, Chicago amazed me with its imposing architecture!

Day two (Saturday)

On Saturday, Chicago welcomed us with sunshine and warm temperatures so we were ready to start exploring the city.

Michigan Ave

Going north to south, this is the main artery of the city.

Tribune Tower

Located on the southern stretch of Michigan Ave, you’ll find the Tribune Tower, home of the famous Chicago Tribune. This building incorporates stone fragments from various iconic places around the world. At the end of the street, just before crossing the river, is the Wrigley Building, a white terracotta building split in two and characterized by its clock.

Millennium Park

Crossing the Du Sable Bridge, we reached Millennium Park, Chicago’s green lung famous for Obama’s speech the night he was elected President. The park’s various quirky design elements include: Frank Gehry’s Jay Pritzker Pavilion, an outdoor concert hall; the interactive towers of Spanish Jaume Plensa that project video images with the faces of Chicagoans and the Bean, a sculpture similar to a drop of mercury that reflects everything around it.

Continuing along Michigan Ave we came across the signs for the famous Route 66, which starts in Chicago and finishes in Santa Mónica. Further south, we reached the Buckingham Fountain, which is right in the middle of Millennium Park. Walking around, we arrived at the Museum Campus, a large lakeside park housing various museums, including the Field Museum dedicated to natural history.

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Bordering the park, you’ll finally reach Lake Michigan and with it comes the best reward: stunning views of the Chicago skyline.

The Loop

A short walk from there is the Loop area. It gets its name from the elevated train system that surrounds downtown. Various bridges span the Chicago River, connecting historic and modern buildings on both sides. After wandering around, we took a ride with the train and enjoyed the view from up there, including old-fashioned stations.

Chicago River tour

Back in downtown, we strolled along the Chicago River before embarking on a 45-minute night cruise to admire the city’s architectural landmarks.

Day three (Sunday)

Unlike Saturday, we woke up to a rainy Sunday.

However, Chicago turned out to be just as photogenic.

Our first stop of the day was in northern Chicago, where we visited outside the stadium of the Chicago Bulls stadium (known as the United Center) to see the statue of Michael Jordan.
After that, we headed back to downtown and strolled around the Theater District area. Then we walked to the Navy Pier, a large recreational complex that includes a Ferris wheel, carousels and other entertainment options.
Finally, we passed by the “beach” on the shores of Lake Michigan before reaching the Hancock Tower and admiring the impressive views of the city from the observation deck and the cafeteria on the 95th floor.
This is a wrap but I hope to see you soon Chicago !!

Where to eat in Chicago

After spending the weekend in the Windy City, this a recap of the places where we ate:

• Rainforest Cafe: we came to this jungle-themed restaurant chain for dinner on Friday night. Nothing exciting about the food though.
• Egssperience: we went to their branch at 35 W Ontario St for breakfast, but they have various locations throughout Chicago. I highly recommend this place to kick off your day. Offering anything going from eggs and burgers to pancakes and chilaquiles, this cheery local restaurant chain featuring classic American lunch and breakfast eats will satisfy your appetite for sure.

• Portillo’s : we enjoyed a nutritious dinner at their 100W Ontario St address. This food chain offers hot dogs, beef, burgers and salad.
• Pizzeria Due: this Chicago institution located in 619 N Wabash Ave is famous for its legendary deep dish pizza. It resembles to a French quiche in height, although it’s a hearty pizza filled with impressive quantities of meats, spices, vegetables and cheese.

• Dick’s Last Resort: this bar / restaurant chain is known for how rude and unpleasant their waiters are with customers. I know, American style. I wouldn’t come here for the food, but hey, if you’re coming for the experience, why not.

Below you can find a map with all the locations mentioned in this blog post, including restaurants as well as historic landmarks and other places of interest. Save it for your next trip!

Trip details

• Transportation: we flew with American Airlines from Ronald Reagan airport in Washington DC to the Chicago O’Hare airport, where we landed after a couple of hours. We took the metro to Downtown (we got off at Clark/Lake station). We flew back early on Monday morning. However, our flight was delayed because of a shooting at Navy Yard in DC.
• Good to know: when in Chicago, remember to adjust to the Central Time zone! Since we came from DC (located in the Eastern Time zone), we had to turn our clock one hour backwards.
• Accommodation; we slept at a friend’s living near the Clark/Lake metro station.

I hope you enjoyed reading this post and that the information here was useful! Feel free to leave a comment below!