a view of chicago buildings over the river

3 Days in Chicago: Architecture & Food

In this blog post, we'll explore how to spend 3 days in Chicago, focusing on the city's world-renowned architecture and delicious iconic food. We'll cover everything you need to know to make the most of your long weekend in the Windy City.

In this article:

Disclaimer: As an Amazon Associate, I earn a small commission (at no extra cost to you) from qualifying purchases made on Amazon in addition to other retailers featured on the blog.

I had the incredible opportunity to spend 72 hours in Chicago with my wonderful local family; I had a blast, especially since I was exploring the city through their eyes. “A big city with the Midwest charm” that’s how they described it to me, and I couldn’t agree more. Friendly people, marvelously designed skyscrapers, and heavenly food – that’s what you get in Chicago!

So pack your bags, grab your camera, and get ready to explore the Windy City!

3 days in Chicago – Things to see

Chicago boasts one of the most awe-inspiring architectural landscapes worldwide. For all the architecture enthusiasts, this captivating city deserves a prominent spot on your must-visit destinations! Its skyline is adorned with numerous iconic structures that once held the title of the world’s tallest buildings. In fact, Chicago is the birthplace of skyscrapers, making it a truly remarkable and innovative architectural hub.

A view over the chicago river at sunset

Day 1:

On day one, we take in the beautiful architecture.

The Willis Tower Skydeck

What’s better than a 360-degree view of Chicago from the Skydeck, located in the Willis Tower (formerly the Sears Tower) – one of the tallest buildings in the world and the second tallest building in North America! Once you head to the 103rd floor, the glass floor ledges will give you an oversight of the city’s architecture. You might feel dizzy, LOL, but it’s worth it!

The Centennial Wheel at Navy Pier

Fun fact: the first Ferris wheel was built in Chicago! It’s not, of course, the current Centennial Wheel, but it gives you an idea of Chicago’s innovation. Located at the Navy Pier, the Centennial Wheel is a nice ride to explore the city’s skyline!

Sunset Walk on Riverwalk

If you love watching sunsets, I highly recommend strolling along the riverwalk. Prepare to be captivated by the breathtaking fusion of majestic skyscrapers and the stunning palette of colors that paint the sky.

A view of the chicago skyline from the michigan lake

Day 2:

Start your day with a brunch (I have some references in the brunch section), and let’s explore the city up close!

The Architectural Boat Tour

It’s NOT TO BE MISSED! Especially if you’re a fan of architecture, we did the Lake & River Architecture Tour with Wendella Tours & Cruises. We started the tour from Lake Michigan for a breathtaking view of Chicago’s skyline, and then we sailed through the Chicago River for an up-close of the architecture and history of the city.

Magnificent Mile

If you’re in the mood for window shopping, head to the Magnificent Mile on Michigan Avenue, which stretches from the Chicago River to Oak Street. And if you visit during springtime, watch out for the vibrant tulips that add a cheerful touch to the street.

Not to miss: after you cross north of the Chicago River, you’ll see two historical landmarks: the Wrigley Building, built in the 1920s, and the Tribune Tower, which, fun fact, has chunks of the Taj Mahal, the Great Pyramid, the Great Wall of China and other famous building fragments embedded in the walls.

The Art Institute of Chicago

The Art Institute of Chicago is the 2nd largest art museum in the country and home to Grant Wood’s American Gothic, one of America’s most famous paintings. Art lovers, you’ll want to add this to your agenda.

Bonus: Tea Time at The Drake Hotel:

If you fancy an afternoon Tea, head to The Drake Hotel on the Gold Coast neighborhood of Chicago at the Magnificent Mile. With 17 unique Tea blends, artisanal finger sandwiches, delicious scones, and more, your taste buds will be delighted!

a photo of the chicago bean with a background of the city

Day 3

On day 3, we’ll stretch our legs exploring the Chicago Loop neighborhood, so fuel on coffee and let’s go!

Start with Grant Park to check out the statue of Abraham Lincoln, Head of State, and the Buckingham Fountain. Then take the Lakefront trail to the Shedd Aquarium, home to 32,000 animals! Next to the Shedd, the Chicago Horizon offers yet another beautiful skyline view.

After Grant Park, you’ll want to walk north towards the famous Millennium Park to explore the famous Cloud Gate, aka the Bean.

From Millennium Park, you can walk across the pedestrian BP bridge to Maggie Daley Park, where you can find a playground, a mini-golf course, and a rock climbing wall.

Where to Eat the Iconic Chicago Foods

Chicago’s vibrant and diverse food scene is an absolute treat! Whatever you do, you must try the iconic deep-dish pizza and mouthwatering Chicago-style hot dogs! I can assure you, you will not be disappointed!

Deep Dish Pizza

This pizza is baked in a round-shaped steel pan that resembles a cake pan. The crust is pressed to the sides of the pan, hence the “deep dish” in its name, and is stuffed with tomato sauce, a LOT of cheese, and your favorite toppings.

Here are the two most famous restaurants in Chicago to try deep-dish pizza:


I had the chance to try the Giordanos pizza during my visit. It’s honestly delicious. If you’re a cheese lover, you’ll love this. We ate there on a rainy day, so the pizza was heartwarming and comforting.

Lou Malnatis

Lou Malnatis also serves the legendary deep-dish pizza. Local Chicagoans often disagree on which of the two Giordanos or Lou Malnatis serves the best deep-dish pizza. Might as well try them both!

Chicago-style hot dog

Unlike other places, the Chicago-style hot dog has 9 ingredients. Yep, you read it right, 9! Here they are the hot dog (duh!), mustard, relish, celery salt, chopped onions, sliced tomatoes, pickle, and sports peppers, all stuffed in a poppy seed bun. Just do NOT attempt to ask them to add ketchup, or else you’ll offend them.

Here are the two most famous places to try a Chicago-style hot dog


The hotdogs at Portillo’s were really flavourful and delicious! They claim to be the “Unrivaled Chicago Street Food.” Bonus point: their fries are so good!


Superdawg also serves the famous Chicago-style hot dogs and is recommended to me by local Chicagoans.

Where to go for coffee

As a coffee lover, I’m always down to try unique coffee shops wherever I travel. Here are 2 unique coffee shops that I went to in Chicago:

Starbuck Reserve Roastery:

Did you know it’s the world’s largest Starbucks? Starbuck Reserve Chicago Roastery is situated on the Magnificent Mile, and the 5-floor building is a whole experience! On the first floor, you’ll find the coffee roaster and the second floor is dedicated to the bakery. The third floor is where you can order coffee and immerse yourself in the art of brewing it. The fourth floor has a cocktail bar (yes, that’s where you can order your espresso martini). The last floor is a rooftop patio.

Goddess and the Baker:

If you’re in the mood for a cute coffee shop, Goddess and the Baker is an excellent choice. I highly recommend trying their Glitter Gold Latte – it’s sure to make you smile. Trust me, the experience is worth it! The sight and taste of this unique coffee are sure to brighten your day.

Where to go for brunch:

Are you a brunch lover? I’ve got you! During my long weekend getaway to Chicago, I tried 2 different Brunch Places, which I highly recommend.

The Hampton Social

Where Rosé all day meets brunch! The Hampton Social offers a delicious boozy brunch with live music! I ordered the Short Rib Benedict, and it was simply delicious! 10/10!

Egg Harbor Cafe

The Egg Harbor Cafe, on E. Illinois St., is a breakfast & brunch place that serves delicious coffee! I tried the Lemon Poppyseed Pancakes, and I highly recommend them! They also make their own jam, so try them with some English muffins!

Where to Stay

I recommend you stay in The Loop neighborhood for the proximity, the culture, and city life!


Chicago is a city that has so much to offer, and it’s impossible to see everything in just three days. However, if you’re looking for a long weekend getaway full of stunning architecture, delicious food, and friendly people, Chicago should be at the top of your list. With a rich history and vibrant cultural scene, there’s always something new to discover. So pack your bags, make sure to check my blog on how to easily pack,  and get ready for an unforgettable adventure in Chicago!

a photo of chicago at sunset with the caption "chicago - 3 days itinerary"
a photo of chicago theater with the caption "Chicago - things to do in 3 days "

Share this post

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.