Unique 4 or 5 days Chicago itinerary – 3 options for different type of travellers

• 4 or 5 days in Chicago itinerary for couples: On Day 1, have a walk in The Loop and take an Architecture Cruise. Reserve Day 2 for the Driehaus Museum and the (in)famous Gangsters and Ghosts of Chicago Tour. Explore the hidden Chicago on Day 3 and leave Day 4 for a foody time. Do you have another day to spare? Rent a bike and ride to Sweden. Read below a detailed daily plan for 4 or 5 days in Chicago for couples, with morning and afternoon activities.
• 4 or 5 in Chicago itinerary for families: Start Day 1 with a visit to the Navy Pier for the Centennial Wheel and the Children’s Museum. On Day 2 take the subway to the Field Museum and Museum Campus. On Day 3, organise a family-friendly River Cruise and spend the afternoon at the lovely Maggie Daley Park. Day 4 is zoo time, and it’s free too. On the optional 5th day, have a cruise in the lake Michigan.Read more below for the best family itinerary with maps and all the attractions for kids.
• 4 or 5 in Chicago for art & culture: Start your trip on Day 1 exploring the famous architecture of Chicago, with a walk and a cruise. On Day 2 spend some time at the Art Institute of Chicago and have a check at the Tiffany Dome. Close the day with some live Jazz bands at one of the most iconic venues. Reserve Day 3 for the Design and Writers Museums and Day 4 for a walk in The Loop. The WNDR and the Photography Museum are the optional destinations for the last day. Read more below for the 4/5 days plan

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

4 or 5 in Chicago itinerary for couples

Day 1 – The Loop & Architecture Cruise

Discover Chicago’s heart by exploring The Loop area.

I recommend starting from the Willis Tower, one of the city’s most beautiful viewpoints.

If you need a bit of adrenaline to begin your day, take the elevator to the 103rd floor, where you will find a part of the observation deck inside sea-through glass boxes.

Pre-book your tickets online and arrive as early as possible in the morning (the museum opens at 9am).

You will have the place almost on your own.

Once you leave the Willis Tower, start your walk through The Loop stopping at the Calder’s Flamingo, the Chagall’s Four Seasons, the Richard J. Daley Center and the Chicago Cultural Center, finishing your stroll at the Cloud Gate in the Millennium Park.

In the afternoon, take an Architecture Cruise along the Chicago River to admire the beautiful skyline with a knowleadgeable guide explaing all about the impressive Chicago architecture.

You can read more about the river cruise as well as the walk, with a description of the 9 stops, on my day in The Loop.

Day 2 – Driehaus Museum, Gangsters and Ghosts

On your second day in Chicago, explore more of the history on this unique city, usual and unusual.

In the morning, head to River North to explore the 19th century Richard H. Driehaus Museum, a beautiful mansion restored to its glorious art nouveau era.

Take the famous Magnificent Mile (N Michigan Avenue) to head back to The Loop.

This is the most popular shopping strip in Windy City.

Getting hungry? 

You can decide to stop at the Purple Pig Restaurant, for a trendy lunch, or the Billy Goat Tavern for a budget meal in an old style diner environment.

In the afternoon, it is time for the unusual history of the city made of gangsters and ghosts.

Join this 2 hours Famous Gangsters Tour to get a full picture of the undercover Chicago

You can read more about the Driehaus Museum and the history of crime in Chicago, including interesting and funny facts, on my history day in Chicago.

Day 3 – The hidden Chicago

Chicago’s hidden gems will be exposed in this day, places that you will never find in a printed guide, off the beaten track.

Add to your bucket list the following destinations:

• the Church in the sky, world’s tallest church, perched atop a skyscraper. There are regular services in the church, as well as free daily tours (unfortunately, the tours have been suspended temporarily due to Covid).
• the Money Museum at the Federal Reserve Bank of Chicago
• the International Museum of Surgical Science in the afternoon (Red Line to Clark/Division station).

For latin/asian inspired food on a budget, checkout Saucy Porka, right in The Loop, close to the Money Museum.

Take a Lake Michigan dinner cruise on the Spirit of Chicago for one of the most memorable experiences in the Windy City, with dancing and a DJ.

Read more about the hidden Chicago, with a description of the above destinations.

Day 4 – Food culture in Chicago

This is a day where you can explore the food culture of the city.

In the morning join this 2.5-Hour Food Walking Tour where you will be guided around the city to taste Chicago’s favorite food.

The great thing is that you will get to try so much food that your lunch is basically done, making the cost of this experience a real bargain.

In the afternoon, take the Red Line (6-7 minutes) to the Cermak-Chinatown station to experience more of the Chinese cuisine.

Walk through the typical Chinatown Gate for a few photos

Start your exploration from the Chinese American Museum of Chicago for a better understanding of the history & culture of Chinese-Americans.

Than have a walk to the Chinatown Square Plaza where you can select one of these two restaurants for your dinner.

• Veggie House for vegetarian and vegan food
• Golden Bull for a tasting experience (most dishes are offered in both main and starter size) 

Day 5 (optional) – Bike ride to Sweden

Rent a bike for a day to explore the north shore of Lake Michigan.

Visit Lincoln Park, a large lakeside area that is home to the Lincoln Park Zoo.

You can hop off your bike and explore some amazing animal exhibits. Admission is free which helps with the budget.

Keep riding north to the Cricket Hill, for the lovely view and on a warm day have a stop at the Montrose Public Beach for a swim.

Keep riding along Foster Beach and turn left into the residential area to have lunch and explore the Andersonville neighborhood.

You may feel suddenly catapulted in Sweden with its many Swedish bakeries, cafes and, of course, furniture shops. 

Leave the bike and walk through the streets with their famous 19th-century row houses.

Finally, spare some time for the Swedish American Museum.

What an active day!

Accommodations and experiences for couples:

• Best Hotels: Kinzie Hotel (good value in River North), Wicker Park Inn (bed and breakfast in Wicker Park), 
• Stylish Hotels: Aloft (good value in River North), Virgin Hotel (great value in The Loop)
• Hostels & Cheap: Found Hotel (good location in River North, practical design), Travelodge by Wyndham (shared bathroom, in The Loop)
• Organised experiences:
  • Architecture Cruise
  • Willis Tower Observation Deck
  • 2 hours Famous Gangsters Tour
  • Lake Michigan dinner cruise
  • 2.5-Hour Chicago Food Walking Tour
  • Rent a bike for a day

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

Check more photos below of a 4 or 5 in Chicago itinerary.

4 or 5 in Chicago itinerary for families

Day 1 – Centennial Wheel & Children’s Museum

The Navy Pier is a great place to begin a family breakaway, with plenty to see and do.

Take a ride on the Centennial Wheel to see the city from the top.

When visiting during school holidays and weekends, I recommend buying your tickets online to avoid the line.

The Relish Hot Dogs, at the start of pier, are a tasty lunch option, even though probably not the healthiest option 🙂

Spend the afternoon at the Chicago Children’s Museum, where children of all ages can enjoy interactive exhibits.

Read more on the Navy Pier and the museum on my Chicago for families.

Day 2 – Field Museum and Museum Campus

This is a full day dedicated to the Museum Campus area south of downtown.

It is a beautiful organised area where you can visit the outstanding Field Museum of Natural History (pre-book your ticket because the number of visitors is limited to avoid crowds) with the world’s largest Tyrannosaurus Rex.

Moreover, you can have a swim at the local beach, spend the afternoon at the Shedd Aquarium or the Adler Planetarium, with its Skyline Walk, and so much more to do.

Check out all you need to know about the Museum Campus before doing your visit.

Day 3 – River Cruise and Maggie Daley Park

Take advantage of a Family-Friendly Architecture Cruise in the morning, arranged to be fun and entertaining for kids as well as for adults.

In the afternoon, experience the Cloud Gate, Chicago’s most iconic sight in the Millenium Park.

When you see this gigantic mirror-made bean, you can’t help but take some unforgettable pictures.

Afterwards, go to the Maggie Daley Park, which has one of the best playgrounds in the world, regardless of age.

During the winter, the park features also a ice skating rink shaped around the climbing areas.

Honestly, there is no better place to spend an entire day with the kids, though, if you prefer to add more sightseeing time, you can also explore the nearby Cultural Center (entrance is free).

Day 4 – A visit to the zoo

Take the #151 bus from the loop to the Lincoln Park Zoo.

Entrance is free, which is great for the family budget.

Founded in 1868, it is the fourth oldest zoo in the USA.

The Lincoln Park Zoo is home to over 1,100 animals including reptiles and monkeys.

It sits on 35 acres of prime estate in Lincoln Park.

The collection started with 2 swans gifted to the former Lincoln Park commissioners.

Soon after, more animal donations were made, like peacocks, elks, wolves, eagles and even a puma.

Over time, more animals found a home here at the Zoo, and a Lion House was built in 1912.

Later, after some renovations, a primate house was constructed.

The Regenstein Macaque Forest was opened in 2014, where you can see snow monkeys.

A panda enclosure and an African penguin habitat were opened later in 2016. 

You can also visit the Pritzker Family Children’s Zoo, the Kovler Seal Pool, the Regenstein Birds of Prey Exhibit, the Farm-in-the-Zoo and so much more.

Be ready for quite the adventure, but in comfortable shoes.

You will find plenty of other attractions around the zoo, like the Lakefront Trail, the North Pond Natural Area, with its beautiful wildlife area, many beaches, great on a summer day, the Bill Jarvis Migratory Bird Sanctuary, and I could keep going.

Day 5 (optional) – A lake Michigan Cruise

Book your lunch aboard the Odyssey for a Lake Michigan Cruise.

This is a marvellous experience lasting 3 hours in the water with an unrestricted view of the Chicago Skyline, something to remember for a long long time.

Another possibility is to visit the Museum of Science and Industry where you can enter also the U-505, the first Nazi U-Boat to be captured by the allies during WW2.

The museum is very child-friendly with hands-on exhibitions.

Once known as the Palace of Fine Arts, it was opened in 1933.

It is considered to be one of the largest science museums in the world.

Picture, if you will, over 400,000 square metres of exhibitions that will make you curious about science and boost your creativity.

This is home to over 35,000 artefacts. There are many permanent and seasonal exhibitions which you will enjoy all year round.

When you enter, you will find an 800-seat auditorium, 2 smaller theatres, an e-learning centre and so much more.

It is here that you will find Chicago’s only 5-storey movie theatre. You will be amazed by its dome design.

Accommodations and experiences for families:

• Best Hotels: Hyatt Centric (lux, in The Loop), Warwick Allerton (the deal in the Magnificent Mile)
• Best Airbnb/Apt: Essex on the Park (1BR and 2BR, in The Loop), Jewelers Row (1BR and 2BR, in The Loop), Kasa (1BR and 2BR, in the Magnificent Mile)
• Organised experiences:
  • Family-Friendly Architecture Cruise
  • Centennial Wheel skip-the-line tickets
  • Field Museum of Natural History pre-booked ticket
  • Lake Michigan Cruise for families

Check more photos below of a 4 or 5 in Chicago Itinerary.

Four or five days in Chicago for art & culture

Day 1 – Chicago Architecture

Experience Chicago from the water on an Architecture Cruise in the morning.

In the afternoon, marvel at the city’s Art déco and postmodern design.

With this Downtown Architectural Interiors Tour, you will discover a few hidden gems in The Loop and get an insight by the knowledgeable guide about the design implemented in the construction of those buildings.

Read more about the Chicago architecture, the art déco and post modern design.

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

The day begins with a visit to the Art Institute of Chicago, one of the world’s largest museums housing almost 300,000 pieces of artwork (read more on the Institute here).

Purchasing the skip-the-line tickets online is the best way to avoid the typical long queue, which can sometimes last 1-2 hours.

Take in the beauty of Tiffany’s dome at the 1897 Beaux arts Cultural Center.

There is plenty to see and do at the center, but don’t overwhelm yourself, as an evening of live music awaits.

After dinner, head to the Green Mill Jazz Club, one of the most historical jazz venues in Chicago, where even Frank Sinatra performed in his days.

During the days of Al Capone, this club was also the place where the mafia met (I recommend watching the old but still great movie The Joker Is Wild, especially if you’re visiting Chicago).

Nowadays, this is THE place where you can hear some of the best jazz in the country.

Day 3 – Design & Writers Museum

On your third day, visit the Design Museum of Chicago to learn about Chicago design applied to everyday objects as well as buildings.

Visit the American Writers Museum in the afternoon, where you can see a diverse collection of books, typewriters, and other writing-related items.

Read more about the Design Museum as well as the Writer Museum here.

Day 4 – The Loop walk and Fine Arts Building

In the morning, follow the walk in the map below that goes through:

• Willis Tower, where you can have the best viewpoint of the city (pre-book your tickets online)
• Calder’s Flamingo
• Chagall’s Four Seasons
• Sculpture By Joan Miró
• Richard J. Daley Center
• N State St (the Iconic street)
• Marshall Field and Company Building
• Chicago Cultural Center
• Millennium Park and the Cloud Gate

If you still have time in the day, have a check to the Fine Arts Building, a historic Art Nouveau building with one of the oldest elevator in the city, still running with an actual operator.

The building has been in existence since 1898 and is a haven for all types of artists.

Inside, you will find 2 performance spaces, namely Carriage Hall and the Studebaker Theater.

You will also get to marvel at Art Nouveau murals. These can be found within the Fine Arts Building that were created in the late 19th century.

Day 5 (optional) – WNDR and Photography

In the morning, make your way with the Blue Line (Racine Station) to the WNDR Museum for its contemporary exhibitions stimulating all 5 human sensors.

The WNDR is a wild mix of art & technology.

What was once a pop-up installation has become a permanent spot for art lovers.

One of the exhibits you must experience is the WNDR Light Floor.

It is an exhibit with hundreds of motion sensored LED panels and sets of these screens move in different directions to bring the piece to life (hard to describe, engaging to experience).

Other exhibits include Boxed In, Oracles of WNDR, Colorbox, Everbright, Flux Room and the Projection Dome among others.

There is always something to excite and amaze you here.

One of the most interesting exhibits is Yayoi Kusama Infinity Room “Let’s Survive Forever” where you will have just one minute to experience the artistic genius of this installation.

Close your Chicago trip with the Museum of Contemporary Photography, in The Loop.

The Museum of Contemporary Photography, also known as MoCP, can be found at the Columbia College Chicago. 

It was started back in 1976 for students, teachers and the public to learn more about photography.

You will find seasonal exhibitions by people like Ralph Arnold, Dawoud Bey and Ai Weiwei among others.

Other famous exhibitions are American Epidemic: Guns in the United States and Beautiful Diaspora/ You are not the Lesser Part.

I highly suggest checking the museum website for the latest openings.

Alternatively, for a more culturally immersive experience, you can also explore Chinatown and taste some of the local favorite food on this 2.5-Hour Taste of Chinatown Food Walking Tour.

Accommodations and experiences:

• Best Hotels: The Gwen Collection (lux in River North), Hyatt Centric (lux in The Loop), Nobu Hotel (Celebrity style in West Loop)
• Best Boutique Hotel: Chicago Athletic Association (unique in The Loop), The Robey (minimalistic boutique with rooftop pool in Wicker Park)
• Organised experiences:
  • Architecture Cruise
  • Downtown Architectural Interiors Tour
  • Art Institute of Chicago skip-the-line ticket
  • 2.5-Hour Taste of Chinatown Food Walking Tour

More photos of the 4 or 5 Chicago Itinerary