Last updated on May 9, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Chicago

Unique 2 days in Chicago itinerary – 3 options for different types of traveler

Organizing a 2 days in Chicago itinerary is a real challenge. There is so much to see and do.

That being said, plan it well in advance, with maps and walks, and you will be pleasantly surprised by how much you can see and experience.

Below, you will find three types of travel plans that work so well for couples, families, and art & culture lovers.

Chicago is such an amazing city that you will fall in love and come back for another trip, this time for a longer stay.

Let’s jump to the juicy stuff

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 2 days in Chicago itinerary
Unique 2 days in Chicago itinerary

2 days in Chicago itinerary – in a nutshell

Here is a quick map of the top areas to stay and visit in Chicago.

With 2 days in Chicago, I would suggest visiting mostly places and attractions in the city downtown. With 3 days in Chicago or more, you can think of exploring more of the nearby areas.

Best areas to stay in Chicago
Best areas to stay in Chicago (check Google Map for Interactive View)
  • 2 days in Chicago itinerary for couples: on Day 1 take an Architecture Cruise and have a self-guided walk in The Loop. Start Day 2 by visiting the unique Driehaus Museum and take a Gangsters and Ghosts Tour, the best way to experience the (in)famous criminal history of the city. Read below a detailed daily plan for 2 days in Chicago for couples
  • 2 days in Chicago itinerary for families: Chicago is such a fun city for kids. Start Day 1 with a family-friendly River Cruise, then head to the gigantic bean (Cloud Gate) and enjoy the Maggie Daley Park (playgrounds, ice rink, play areas, etc). Reserve Day 2 for the Navy Pier where you will find the Centennial Wheel and the Children’s Museum. Read more below for the best family itinerary with maps and all the attractions for kids.
  • 2 days in Chicago for art and culture: the city architecture and design will monopolize Day 1, meanwhile on Day 2 plan a visit to the Art Institute of Chicago and explore the interior of a few amazing city buildings. Read more below for the art & culture option

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)

2 days in Chicago itinerary for couples

Day 1 – Architecture Cruise & The Loop

Start your trip to Chicago from the water, with an Architecture Cruise to fully appreciate this city.

This cruise through the Chicago River will let you fully experience the beautiful architecture of this unique city.

Some of the buildings you will be able to take memorable photos of include the Lyric Opera House, the Old Post Office, the 360 Chicago Observation Deck, the Willis (Sears) Tower and the Wrigley Building.

Other spots you will experience include the Millenium Park, the John Hancock Centre, the Historic Water Tower and the Chicago Riverwalk.

There is something for everyone while on the cruise.

The tour lets you experience the beauty of around 40 landmark buildings.

While on the cruise, you will learn which buildings were designed by top architects like Skidmore, Mies van der Rohe and Helmut Jahn.

During the summer, remember to take the sun cream with you.

Architecture Cruise Ticket

In the afternoon, explore the loop with a walk to end at the Willis Tower, an observation tower with glass boxes on the 103rd floor. You will feel suspended in the air.

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

Start your walk from the iconic Cloud Gate in the Millennium Park

  • The Cloud Gate is a well-known sculpture by Indian artist, Anish Kapoor. It is found right outside the AT&T Plaza. It is known as ‘The Bean’ due to its obvious shape.
  • Then, head to the Chicago Cultural Center that was built over 100 years ago to host the Chicago Public Library and a Civil War memorial. This is where you will also see the famous Tiffany Dome
  • Next stop is at the Marshall Field and Company Building, which is the mid-western headquarters of the Macy’s chain of department stores.
  • You will arrive at N State St, an iconic street that you must check out while on the Loop tour. It is here where you will find 108 North State Street, also known as Block 37. Other landmarks include Marina City, ABC7 News Studio, The Original Playboy Mansion and the Chicago Theatre, among others.
  • Richard J. Daley Center is next, previously known as the Chicago Civic Center. It is at the heart of the Loop. Many private and public events are held here. Many films are also shot here. You will appreciate the beautiful and classy design of the building.
  • Along this tour, you will be able to see Miró’s Chicago, a sculpture by renowned artist Joan Miró. It was originally called The Sun, the Moon and One Star.
  • Next is the Chagall’s Four Seasons, a mosaic initially created in Chagall’s french studio. It was transferred onto panels and installed in Chicago. It has inlaid chips of up to 250 colors and tells the story of Chicago’s six scenes.
  • Then, check out Calder’s Flamingo. This is an enormous sculpture made of steel and glass. It is 53 feet tall and weighs 50 tons. It pops out with its bright colors.
  • Finally, you will arrive at the Willis Tower, the observation tower, with its unique and amazing view of the city (buy the tickets in advance to skip-the-line).

Willis Tower Ticket

It is going to be an intensive day.

This is usually the plan I suggest as a reference for people visiting Chicago in just 1 day. And it works so well also as a start of a 48 hours stay.

Day 2 – Driehaus Museum, Gangsters and Ghosts

The second day is focused on the history of Chicago.

Start the morning with a visit to the Richard H. Driehaus Museum, a restored 19th-century mansion turned into a museum in River North.

The Richard H. Driehaus Museum hosts a collection of pieces celebrating architecture, art and design.

It is not far from the Magnificent Mile and is hosted at the Samuel Mayo Nickerson Mansion.

There are permanent and temporary exhibitions held here all year round.

But it’s not only about the exhibits, it’s also about the architecture of the original mansion, restored as it used to be in the golden era.

You will enter the museum from the Main Hall, designed with marble and beautiful pieces.

The reception room has some decorative art objects from the Driehaus Museum’s collection.

The centerpiece, known as Nautilus Shell Lamp, is a must-see.

There are many other rooms to visit, like the ballroom, the library, the Maher Gallery and the drawing room.

Each room has many unique pieces that you can appreciate.

For example, the drawing room hosts Saint Cecilia by Sidney Harold Meteyard. In the same room is the Chickering & Sons grand piano.

You can also check out A Wanderer in the Elysian Fields by Charlotte Major Wyllie and Agnes Northrop’s Landscape.

There are pieces of furniture and decor pieces that will impress any art and design lover, all original pieces.

If you have still some time left, make your way back to The Loop through the Magnificent Mile (N Michigan Avenue), Chicago main shopping area

In the afternoon, explore the dark side of Chicago, famous for its gangsters and ghosts

To get the best out of it, you should join this 2 hours Famous Gangsters Tour that will take you to a few amazing places.

One thing that people know about Chicago is the active Mafia culture that was rich back in the day.

This was common in the 1920s and 1930s. While on this tour, you will learn of the ghosts that still roam about the city.

The Chicago Loop District is rich with stories from that era, so you will learn something interesting as you go along.

Some of the spots you will hear about are the speakeasy saloons, as well as the secret underground tunnels where shady business was running.

Learn about one of the most famous gangsters, Al Capone. He was well known to carry out business and live a good party life on his day.

The tour guide will also tell stories of how the law of the land was back in the day. You will also hear about the rival gangs of Chicago.

Some of the places you will visit include the Palmer House, Death Alley and the Congress Hotel.

To finish off this 2 days in Chicago itinerary in a memorable way, book a Lake Michigan dinner cruise, including food and music with a DJ aboard the beautiful Spirit of Chicago

Gangsters Tour Ticket    Lake Michigan Cruise Ticket

Accommodations and experiences for couples:

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

Chicago downtown city skyline
Chicago downtown city skyline

Check more photos below of a 2 days in Chicago itinerary.

2 days in Chicago itinerary for families

Day 1 – River Cruise, Cloud Gate and the Maggie Daley Park

Start your trip with a Family-Friendly Architecture Cruise, made in a fun way to entertain the kids and to make it interesting for the adults.

This dedicated cruise that traverses the Chicago River is perfect for your whole family.

You can enjoy the scenery on the open decks for the perfect view.

It has a live commentary with an family-friendly guide that will share interesting facts about the buildings that the cruise will pass by.

The cruise starts from Lakeshore Drive and ends at the Willis Tower, passing by the South river branch. The cruise then heads towards Lake Michigan.

For the kids, they will love the large, beautiful buildings and the skyline. The adults will be able to enjoy facts about the architects and the full-service cash bar.

Remember to take some photos and appreciate this traffic-free way of experiencing Chicago.

Family Architecture Cruise Ticket

In the afternoon, head to the most iconic site of Chicago, the Cloud Gate in the Millenium Park.

This is the famous gigantic mirror-constructed bean, a great spot for a few memorable photos.

Then head to the Maggie Daley Park, one of the best playing areas in the world I would say, for any age.

You will find an enormous playground for kids, climbing areas, water features and even an ice skating rink in winter.

This is a great place to spend the entire day, however, if you have still some spare time, you can always think of spending an hour or two at the nearby Cultural Center (free entrance)

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

Day 2 – Centennial Wheel & Children’s Museum

In the morning, head to the Navy Pier, where you will spend the day.

Start on the high with a run on the Centennial Wheel, where you will have a beautiful view of the city and the lake too.

The original Ferris Wheel came to the US in 1893 and was initially meant to rival Paris’ Eiffel Tower.

The present Navy Pier Wheel was added on July 1, 1995, and changed the Chicago skyline forever.

The original one was 150 feet tall and each of the 40 gondolas could fit up to 6 passengers.

Fast forward to 2016 and the wheel installed to celebrate the 100th year celebration of the Pier stood at over 200 feet.

It has gondolas that are covered so that visitors can now enjoy rides no matter the weather conditions.

It is a key part of the Chicago Skyline and a must-visit for any family.

I highly suggest here to pre-book your tickets to skip the line, quite common on weekends and school holidays.

Centennial Wheel Ticket

In the afternoon, visit the Chicago Children’s Museum, an interesting place with engaging hands-on exhibitions.

Back in 1982, a collaboration between the Education Resource Center, Columbia College, and Loyola University gave rise to what was initially called Express-Ways Children’s Museum.

The museum has STEM projects, arts programs, imaginative play sessions and so much more.

Over 11 million children have walked these corridors.

You will be able to visit spaces like the Cloud Buster, Kovler Family Climbing Schooner, the Art Studio, Kids Town, The Story Hub, the Dinosaur Expedition and so much more.

There is something for everyone, doesn’t matter the age.

The museum has a year-round program that the kids can visit and enjoy.

For example, there is Pritzker’s Playspace: Light and Shadow Play. This will let kids explore the world of light and shadows.

An upcoming project is the Street Art Mural, inspired by Hebru Brantley. Kids will get to create art which will be added to the overall mural. 

Accommodations and experiences for families:

Navy Pier in Chicago
Navy Pier in Chicago

Check more photos below of a 2 day in Chicago Itinerary.

Two days in Chicago for art & culture

Day 1 – Architecture and Design

In the morning, plan an Architecture Cruise, a great way to see Chicago from the water explained by the knowledgeable guide.

This is the same cruise I talked about in the 2 days in Chicago for couples section above.

Architecture Cruise Ticket

In the afternoon, visit the Design Museum of Chicago, where you will discover more about the design and architecture of this beautiful city

It was formerly known as Chicago Design Museum, it was a volunteer-run project and it was focused on pop-up exhibitions.

Today, it hosts 2 permanent exhibitions and attracts more than 175,000 tourists annually.

An interesting fact is that this museum was built on sacred grounds of the Three Fire Peoples: the Ojibwe, the Odawa, and the Bodewadmi.

The land was used by over a dozen tribes. It was a land that was primarily used for trade, healing, and gathering.

One of the current exhibitions is the All Together Now: Sound × Design. It is a collaboration of designers, artists and musicians who were chosen by a jury panel.

The project is a way to celebrate sound, music and design.

An annual exhibition that is held to celebrate artists from the city is the All-City Visual Arts Exhibitions.

The most recent one was in partnership with the Chicago Public Schools Department of Arts Education.

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

Day 2 – Art Institute of Chicago

Start the day with a visit to the unmissable Art Institute of Chicago, one of the largest art museum in the world with nearly 300,000 artworks.

One of the most popular pieces of art at the museum is Grant Wood’s American Gothic.

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

Another piece is the 1884 A Sunday on La Grande Jatte by artist Georges Seurat.

There is also Jordan Casteel’s ‘Barack’, which is a depiction of America’s 44th president.

There are also sculptures to check out at the Museum. One of them is the Hero Construction and which was created in 1958.

It is a piece made of many recycled parts from automobile and pipes.

You can also see the Ngady Mwaah Mask which tells the story of the tribe of Kuba.

There is also the amazing Field Armor for Man and Horse, which tells the story of heroes at war.

In terms of unique pieces to check out, there is also the Hartwell Memorial Window created by Agnes F. Northrop over 100 years ago.

It’s made of different glass pieces and about 48 panels.

This is a popular attraction, and it’s highly recommended to buy online the skip-the-line tickets to avoid the usual queue, sometimes even 1-2 hours long.

Art Institute Ticket

In the afternoon, dig deeper into the Art déco and postmodern architecture of the city.

Join this Downtown Architectural Interiors Tour that will take you to a few buildings in The Loop where you will be guided through the different types of architecture used in the construction.

The first building you will see is the Carbide and Carbon Building, which was completed in 1929.

It looks like a champagne bottle and has real gold leaf decorations. A luxury hotel is hosted here.

The other building is the Chicago Motor Club Building, which pays homage to the world of motors. It has a remarkably high ceiling and a 29-foot mural on the side.

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

You will notice that each of these buildings shows the opulence and class that they represent.

Architecture Interiors Tour Ticket

Accommodations and experiences:

Chicago is famous for its iconic architecture
Chicago is famous for its iconic architecture

More photos of the 2 days Chicago Itinerary

Chicago skyscrapers
Chicago skyscrapers
A foggy day in Chicago
A foggy day in Chicago
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
Tiffany dome in the Cultural Center
Tiffany dome in the Cultural Center
Chicago Board of Trade Building
Chicago Board of Trade Building
The financial district of Chicago
The financial district of Chicago
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 - Founder and Editor

About the Author

Stefano is a seasoned travel expert and the visionary founder of, 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.

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