Last updated on February 21, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Chicago

Unique 3 days in Chicago itinerary – 3 options for different type of travellers

Three days in the Windy City will give you a chance to see so much.

The best way to make sure you don’t miss any attractions and local gems is to pre-plan your 3 days in Chicago itinerary.

Listed below are three detailed daily itineraries that are perfect for couples, families, and art and culture lovers.

One plan does not fit all in this amazing city.

Let’s dig into it

Unsure of where to stay? Check out my guide to the best areas of Chicago based on your type of trip (family, couples, nightlife, with or without car, etc)

Unique 3 days in Chicago itinerary
Unique 3 days in Chicago itinerary

3 days in Chicago itinerary – in a nutshell

I have added below a map of central Chicago with my favorite areas to experience and stay.

By having more than 2 days in Chicago (the shortest stay I can imagine in this iconic city), you will be surprised by how much you can actually see and do.

Would it be better to spend actually 4 days in Chicago? Well, you can take things in a more relaxed way and/or you can add a few hidden gems that would be otherwise very hard to fit in.

In saying that, 3 days is a great length of time to explore the Windy City.

Best areas to stay in Chicago
Best areas to stay in Chicago (check Google Map for Interactive View)
  • 3 days in Chicago itinerary for couples: on Day 1 explore The Loop, the heart of Chicago, with a walk and take an Architecture Cruise in the afternoon. On Day 2 visit the Driehaus Museum and take a fun Gangsters and Ghosts Tour to learn more about the (in)famous history of the city. Leave Day 3 for the hidden gems of Chicago. Read below a detailed daily plan for 3 days in Chicago for couples
  • 3 days in Chicago itinerary for families: Head to Navy Pier on Day 1 for the Centennial Wheel and the Children’s Museum. On Day 2 take the Subway to Museum Campus for the Field Museum. Finally, on Day 3, take a Family-friendly River Cruise and spend the remaining part of the day at Maggie Daley Park. Read more below for the best family itinerary with morning and afternoon activities
  • 3 days in Chicago for art & culture: Explore Chicago Architecture on Day 1. Then head to the Art Institute of Chicago on Day 2. Add on this day also a visit to the Culture Center, for the beautiful Tiffany Dome,an a Jazz adventure for the night. On Day 3 you can vitit the Design Museum and the Writers Museum, or, alternatively, explore Chinatown. Read more below for the 3 days plan with a detailed itinerary for each day in Chicago

Here is a Google map I have organized with all the things to see, do and experience in Chicago. You can save it or print it for future reference.

Things to do, see and experience in Chicago
Things to do, see and experience in Chicago (check out the interactive Google map)

3 days in Chicago itinerary for couples

Day 1 – The Loop & Architecture Cruise

Start your trip by discovering The Loop area, the heart of Chicago.

Start from one of the most beautiful viewpoint of the city, the Willis Tower.

Take the elevator to the 103rd floor for the observation deck, partially made with sea through glass boxes that stand outside the building (just in case you need some adrenaline to start your day).

Plan your visit as early as you can in the morning (opening time is 9am) and pre-book your tickets online.

This is the best way to avoid the usual queue and share the place with just a bunch of people.

Next stop is the Calder’s Flamingo, an imposing bright sculpture that stands at 53 feet.

Chicago - The Loop walk
Chicago – The Loop walk (download or print the Google map)

Check out the mosaic at the Chagall’s Four Seasons, made of inlaid chips of up to 250 colors.

Another artwork to see on the way is the sculpture by Joan Miró, originally called The Sun, the Moon and One Star.

Next, head to the Richard J. Daley Center, formally known as the Chicago Civic Centre.

It’s at the heart of the Loop and a well-known movie backdrop and space for events.

Take a stroll along the iconic N State St. Here you will see Block 37 and other landmarks such as the ABC7 News Studio and the Chicago Theatre.

Next, you can view the heart of Macy’s department stores in the Midwest, the Marshall Field and Company Building.

The next stop is the Chicago Cultural Center, which has been around for over 100 years.

Step inside to see the beautiful Tiffany Dome.

Your last stop is the Millennium Park and the Cloud Gate. The sculpture, popularly known as ‘The Bean’, is outside the AT&T Plaza.

In the afternoon, book an Architecture Cruise to discover the beautiful buildings of Chicago from the water.

This cruise along the Y-shaped Chicago River is the best and hassle-free way of learning about the city architecture and skyline.

The tour goes through notable buildings that you must take photos of.

Some of the architectural masterpieces you will see include the Lyric Opera House, the 360 Chicago Observation Deck, the Wrigley Building, the Willis (Sears) Tower and the Old Post Office.

Along the cruise are more sights like the John Hancock Center, the Millenium Park, the Historic Water Tower and the Chicago Riverwalk.

You will also get to learn more about architects like Helmut Jahn, Skidmore and Mies van der Rohe.

It is going to be an intensive day. This is what I usually suggest doing with just 1 day in Chicago. Having a second day will allow you to explore also the dark side of the city.

Architecture Cruise

Day 2 – Driehaus Museum, Gangsters and Ghosts

Chicago’s history is the focus of the second day.

Visit the restored Richard H. Driehaus Museum, a 19th-century mansion turned museum, in River North.

It has been renewed over time, but it has kept its original integrity as a site to enjoy art, design and architecture.

When you enter the museum, you will see the Main Hall, with its marble design.

Each room at the museum has amazing items and art to check out.

For example, in the Drawing Room, there are pieces like the Saint Cecilia by Sidney Harold Meteyard, Charlotte Major Wyllie’s A Wanderer in the Elysian Fields and Agnes Northrop’s Landscape.

In the reception room, there is the Nautilus Shell Lamp, the centerpiece.

Next, have a look at the ballroom, the library and Maher Gallery.

Aside from the artworks, there are also interesting decorative pieces like the Chickering & Sons grand piano.

For lunch, have a walk on the nearby Magnificent Mile (N Michigan Avenue), the main shopping area of the city.

The Purple Pig Restaurant is the chic and memorable choice, although it won’t come cheap.

The iconic Billy Goat Tavern is the budget option. It’s like stepping back in the past with its diner look (burgers are fabulous).

Spend the afternoon discovering Chicago’s dark side, (in)famous for its gangsters and ghosts.

The best way to enjoy it is to take part in this 2 hours Famous Gangsters Tour that will take you to some amazing places.

Between the 1920s and 1930s, the Mafia and gang culture were thriving in Chicago.

With this tour, you will walk the streets that renowned bosses like Al Capone walked.

You will hear of the parties he threw and the deals he made in his time.

This tour will teach you also about the gangsters ghosts that move through this part of the city.

You will see some of the secret underground tunnels and speakeasy saloons where deals were made and goods made their move.

You will also hear vivid stories of the rival gang wars that used to take place.

You will be given a guide through spots like Death Alley, Congress Hotel and the Palmer House.

This is one of the most interesting tours in Chicago

Gangsters and Ghosts Tour

Chicago downtown city skyline
Chicago downtown city skyline

Day 3 – The hidden Chicago

This is a day dedicated to the hidden gems of Chicago, places that you can hardly find on any printed guide, off the beaten path.

The first place is the Church in the sky, the tallest church in the world, on top of a skyscraper

It stands out because it is also in an unusual part of the city.

Known as the First United Methodist Church of Chicago, it was built back in 1831 and is the city’s oldest church.

Here, you will find 21 floors with the well-known traditional church spire on top. The building stands at 568 feet tall.

There is a sanctuary on the ground floor that can hold about 1,000 people.

You will love the stained glass that tells Bible stories and the beauty of the Chicago skyline.

Most of the building holds offices, except the 2nd to 4th floor that has smaller sanctuaries.

The Sky Chapel is at the church spire.

The church runs regular service and daily free tours (unfortunately, because of covid, the tours have been temporarily suspended)

Then head to the unique Money Museum at the Federal Reserve Bank of Chicago.

The Money Museum is an homage to all things money.

You will learn more about the history of the American currency, but, honestly, everyone goes there for the unusual pieces.

For example, there is the machine that sends old bills through glass tubes and into a shredder, with the confetti handed out to visitors as a keepsake.

It will be interesting to know that the bank shreds nearly $10 million daily!

Next is the huge glass cube full of a million dollars in $1 bills.

There is also the elevator shaft that is filled with over $50,000 in coins.

Who said money can’t be fun?

Looking for a place to have a quick and delicious lunch on a budget?

Just walk one block south to Saucy Porka, for latin/asian inspired food.

In the afternoon, make your way (Red Line to the Clark/Division station) to the most unusual International Museum of Surgical Science.

This is 10,000 square feet of public galleries on four floors.

The museum tells the history of surgery through artifacts and artwork.

It started back in 1935 as the International College of Surgeons (ICS).

It was opened to the public in September 1954.

You must visit the Hall of Immortals and the Hall of Murals.

There are also over 600 paintings, sculptures, and prints for your viewing pleasure.

Finish your 3 days in Chicago with one of the most memorable experiences that you can have in Chicago, a Lake Michigan dinner cruise on the beautiful Spirit of Chicago, with a DJ for some dancing too.

Lake Michigan dinner cruise

Accommodations and experiences for couples:

Above accommodation options are mostly in downtown. You can see here other areas of Chicago where I suggest booking your hotel or Airbnb.

The financial district of Chicago
The financial district of Chicago

Check more photos below of a 3 days in Chicago itinerary.

3 days in Chicago itinerary for families

Day 1 – Centennial Wheel & Children’s Museum

Start your Chicago breakaway from the Navy Pier, where you will find lots of things to do and experience.

Get a bird’s eye view as you ride the Centennial Wheel, where you can see the city and the lake.

While at the Pier, you can enjoy food and drinks from the various food stalls and restaurants.

You can also visit the Chicago Shakespeare Theater and the Chicago Children’s Museum.

The Navy Pier hosts many events like the International Carnival, film festivals, kids’ events and cruises.

The original Navy Pier Wheel was added on July 1, 1995, standing 150 feet tall with 40 gondolas.

In 2016, the Centennial wheel was installed to celebrate the 100th year anniversary of the Navy Pier and stood at over 200 feet.

The gondolas have since been covered to let visitors enjoy rides all year round.

I recommend booking your tickets online to skip the line, especially on school holidays and weekends.

I know, hot dogs are probably not the healthiest meal but the Relish Hot Dogs, right at the start of the pier, are such a yummy option for lunch.

In the afternoon, head to the already mentioned Chicago Children’s Museum, with interactive exhibitions to entertain kids of any age.

Previously known as the Express-Ways Children’s Museum, it was opened in 1982 thanks to a collaborative effort of different organizations.

While at the museum, you can see the arts programs, play sessions, STEM projects, and so much more.

The exhibitions and projects at the Museum include the Kovler Family Climbing Schooner, Kids Town, the Art Studio, The Story Hub and even the Dinosaur Expedition.

The museum has year-round programs for kids like the Street Art Mural inspired by Hebru Brantley which has artwork collected from kids and added to the mural.

There are also events like the Pritzker’s Playspace: Light and Shadow Play to help kids explore the world of light and shadows.

Centennial Wheel Skip-the-line tickets

Navy Pier in Chicago
Navy Pier in Chicago

Day 2 – Field Museum and the Museum Campus

Fresh in the morning, head your way to the Museum Campus area south of downtown to explore the Field Museum of Natural History where you will discover the world’s largest Tyrannosaurus Rex.

The museum, located at Chicago’s iconic Lake Michigan shore, was originally built in 1894 and opened to the public in its current form in 1921.

It currently has 40 million artifacts and specimens and it continues to grow its collections over time.

The research, done by over 150 scientists, also looks into ways to conserve ecosystems globally.

Out of the 40 million items collection, only about 1% is actually accessible by the public.

You can learn more about mother earth, the life on the planet, the different cultures in the world and so much more.

The museum has four centers – the Gantz Family Collections Center, the Negaunee Integrative Research Center, the Keller Science Action Center, and the Learning Center.

Each of the above spaces displays different exhibitions, with the Learning Center dedicated to kids and families.

You should check out the Grainger Science Hub that lets visitors interact with specimens.

And then the Crown Family PlayLab, which is a 7,200 square-foot learning center designed for younger kids.

This is a popular attraction of Chicago that tends to get busy during the school holidays and weekends. 

Pre-book your ticket to avoid disappointments because the museum limits the number of visitors to reduce crowds.

Museum Campus is a good area to stay and enjoy the afternoon too.

On a hot day, you can even decide to spend some time at the local beach.

Otherwise, you could think of visiting one or more of below:

  • the Shedd Aquarium
  • the Adler Planetarium, with its Skyline Walk
  • the Chicago Bears training at the open-air field (during the week) or playing at the Soldier Field stadium 
  • the Northern Island Park

Field Museum of Natural History tickets

Day 3 – River Cruise and Maggie Daley Park

In the morning, enjoy a Family-Friendly Architecture Cruise, designed to entertain kids and make it interesting for adults as well.

You will enjoy the skyline and excellent architecture along the Chicago river, in style, thanks to the open viewing decks.

You will learn so much about the history of the buildings along the tour thanks to the kids-friendly live commentary given by the guides.

The cruise will start at Lakeshore Drive, pass by the South River Branch and end at Willis Tower.

Your cruise will then make a U turn and head towards Lake Michigan.

There is a full-service cash bar and an opportunity to take amazing photos.

Take this opportunity to enjoy a tour of Chicago without the crazy city traffic.

Visit the Cloud Gate in Millennium Park, the most iconic sight of Chicago, in the afternoon.

It’s hard not to take some memorable photos at this gigantic mirror-made bean.

Then, go to the nearby Maggie Daley Park, one of the best play areas in the world, regardless of age.

The park features a gigantic playground for children, climbing areas, water features, and an ice skating rink in winter.

There is no better place to spend an entire day, however, if you still have some free time, you can also plan a visit to the nearby Cultural Center (entrance is free).

Family-friendly Architecture Cruise

Accommodations and experiences for families:

The Millennium Park in winter with the ice skating rink
The Millennium Park in winter with the ice skating rink

Check more photos below of a 3 days in Chicago Itinerary.

Three days in Chicago for art & culture

Day 1 – Chicago Architecture

Take an Architecture Cruise in the morning, where your knowledgeable guide will explain the highlights of Chicago from the water.

It is the same cruise (for an adult audience) I previously introduced in the 3 days in Chicago for couples section.

Explore more of the city’s Art Deco and postmodern architecture in the afternoon.

Book this Downtown Architectural Interiors Tour where you will explore and discover a few buildings in The Loop with a guide that will tell you all about the design implemented in the construction.

The tour starts with the beautiful Carbide and Carbon building.

Completed in 1929, it is somehow shaped like a champagne bottle.

You will notice the golden top and green-tinted terracotta facade. The gold detail is real – made with 24 carat gold that was pounded to about  1/5000 of an inch thick.

The building hosts a luxury hotel.

An other building is the Chicago Motor Club Building which pays homage to the motor world.

The building screams success and wealth. It has a high ceiling, linear windows and a 29-foot mural on the side.

Other buildings along the tour include the Civic Opera Building, The Rookery, Chicago Bee Building, TheMART, Adler Planetarium and the Chicago Board of Trade Building.

Architecture Cruise    Architectural Interiors Tour

Day 2 – Art Institute of Chicago, Tiffany Dome and Jazz

Begin the day with a visit to one of the world’s largest art museums, the Art Institute of Chicago. Nearly 300,000 works of art can be seen there.

There are many iconic art pieces you can enjoy at the museum. One of these is A Sunday on La Grande Jatte by artist Georges Seurat.

There is a portrait that celebrates Barack Obama, the 44th US president by Jordan Cateel, aptly named ‘Barack’.

We are sure you will recognize Grant Wood’s American Gothic.

This is a double portrait of a farmer and his daughter (but most people think it’s a couple!).

Sculptures make up a good part of the exhibitions.

There is the Hartwell Memorial Window by Agnes F. Northrop. This is a 100-year old artwork made of 48 panels and glass pieces.

You can also see the Field Armor for Man and Horse and Hero Construction sculptures.

Buy online the skip-the-line tickets to avoid the usual queue at the Art Institute, sometimes even 1-2 hours long.

Spend an easy afternoon at the Cultural Center, a 1897 Beaux arts building with the famous Tiffany Dome.

There is plenty to see and experience at the center, however, don’t overdo, as a long night of music is awaiting you.

For one of the most historical jazz places in Chicago, plan a night at the Green Mill Jazz Club, where Frank Sinatra and Charlie Chaplin used to perform and have a few drinks.

Back in the days, it used also to be the mafia meeting place of Al Capone (you should watch The Joker Is Wild movie, an old but still good one, especially if visiting Chicago).

Today, this is THE place where they perform some of the best jazz in the country.

Art Institute of Chicago skip-the-line Tickets

Tiffany dome in the Cultural Center
Tiffany dome in the Cultural Center

Day 3 – Design & Writers Museum

Start your day 3 with a visit to the Design Museum of Chicago where you can expand your knowledge of the Chicago design applied not only to buildings but also to the everyday objects.

The Design Museum of Chicago was originally only for pop-up exhibitions.

It has grown so much since, and now hosts about 2 exhibitions and over 175,000 guests annually. 

If you love music and design, the All Together Now: Sound × Design exhibition will excite you.

This artwork is a collaboration of designers, artists and musicians chosen by a jury panel.

The All-City Visual Arts Exhibitions is about celebrating artists from Chicago and beyond.

An interesting fact is that the ground where the museum is built is sacred. It was used by ancient tribes like the Three Fire Peoples, the Ojibwe, Odawa, and Bodewadmi among others.

This land was used for trade, gathering, and other activities.

Leave the afternoon for the American Writers Museum, with an extensive and interactive display of books, typewriters and anything related to writing.

Check out first the Nation of Writers exhibit that offers a detailed timeline of American literary history.

You will appreciate the fact that women and authors of color are a part of the story told.

The Surprise Bookshelf and the Word Waterfall are some of the fun sights to see.

Use the collection of usable typewriters to type out your story. Walls and touchscreen tables make the tour even more exciting.

There are many exhibits and events held at the museum annually.

You may also be lucky enough to be there when an author reading session is hosted (check out the website for more information)

Alternatively, you can explore Chinatown with this great 2.5-Hour Taste of Chinatown Food Walking Tour, where you will get to learn more about the American-Chinese culture, tasting some of the favorite local dishes.

Taste of Chinatown Food Walking Tour

Accommodations and experiences:

Iconic DuSable bridge on Michigan Ave
Iconic DuSable Bridge on Michigan Ave

More photos of the 3 days Chicago Itinerary

Chicago skyscrapers
Chicago skyscrapers
A foggy day in Chicago
A foggy day in Chicago
Chicago is famous for its iconic architecture
Chicago is famous for its iconic architecture
Chicago famous Wrigley Building on Michigan Ave
Chicago famous Wrigley Building on Michigan Ave
Beautiful design and architecturew of Chicago
Beautiful design and architecture of Chicago
Chicago Skyscrapers contrast of shapes and colors
Chicago Skyscrapers contrast of shapes and colors
Chicago Board of Trade Building
Chicago Board of Trade Building
Back lanes of Chicago
Back lanes of Chicago
Winding subway of Chicago
Winding subway of Chicago
The elevated subway of Chicago is so iconic
The elevated subway of Chicago is so iconic
Chicago Famous Riverwalk at Night
Chicago Famous Riverwalk at Night
Chicago city Centennial Wheel amusement park at Navy Pier
Chicago city Centennial Wheel amusement park at Navy Pier
The iconic Cloud Gate bean in the Millenium Park
The iconic Cloud Gate bean in the Millennium Park
Cloud Gate - The iconic Bean in Chicago
Cloud Gate – The iconic Bean in Chicago
Millennium Park
Millennium Park
The Magnificent Mile (Michigan Avenue)
The Magnificent Mile (Michigan Avenue)
Chicago skyline with Buckingham fountain in Grant Park at night
Chicago skyline with Buckingham fountain in Grant Park at night
Lincoln Park
Lincoln Park
Chicago lakeshore
Chicago lakeshore
View of Chicago from a cruise boat
View of Chicago from a cruise boat
Deep pizza typical of Chicago
Deep pizza typical of Chicago
Chicago Style Hot Dog with Mustard, Pickle, Tomato, Relish and Onion
Chicago Style Hot Dog with Mustard, Pickle, Tomato, Relish and Onion
A walk in Wicker PArk
A walk in Wicker Park
Stefano Ferro - MEL365.com Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of MEL365.com, a leading travel website with traffic across 6 continents. With a rich background in the travel industry, Stefano spent four pivotal years at Amadeus Travel Distribution System, gaining invaluable insights into travel technologies and distribution.

Leave a Comment