Last updated on February 11, 2024 by Stefano Ferro, founder of MEL365, following extensive travelling in Chicago

Best 10 Chicago Itinerary options, from 1 to 7 days  – for couples, families, art and culture

This guide includes 10 different Chicago itinerary options that work so well for any length of stay.

They have also been developed to cater to different types of visitors. These may be a couple, a family with kids, art enthusiasts, or active travelers that want to see as much as possible.

This city does not have a single plan that works for everyone. There are so many things to do, experiences to have, sights to see and activities to partake in that you could easily stay more than a week and never get bored.

I have included a morning and afternoon action plan for every Chicago itinerary.

As well as recommending restaurants and cafes to eat lunch or dinner, I also suggested a few cocktail bars to spend the evening.

And, most importantly, It is easy to customize each Chicago itinerary to meet your specific needs.

Let’s start now

Best Chicago Itinerary options
Best Chicago Itinerary options

1 day in Chicago itinerary

Honestly, there is so much to do that you should spend at least a couple of days in the Windy City.

You will feel so rushed in doing all in 24 hours.

In saying that, if one day is all you have, check out the map below with all the attractions I have highlighted in the city.

That is a good starting point.

Things to do, see and experience in Chicago
Things to do, see and experience in Chicago – Check out the interactive Google Map

I highly suggest staying in The Loop, that is the heart of downtown and Chicago.

This is the area with the highest number of attractions.

Doesn’t matter if you travel with or without kids, you will find plenty of activities, galleries, museums, playgrounds, unique places and I could keep going

I would recommend taking an Architecture Cruise in the morning to explore the city from the river with a trained guide explaining all you need to know about the city planning and design.

In the afternoon, have a walk to explore The Loop (see map below) that finishes at the Willis Tower, with its amazing observatory area on the 103rd floor.

Part of the viewing platform is built in glass boxes and you feel like suspended in the air, a real pump of adrenaline.

Pre-book your tickets online to avoid the usual queues.

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

You can check out more information on both the cruise and the walk here, including a description of all the 9 stops along the walk

2 days in Chicago itinerary

Two days in Chicago is such a tight time to explore this beautiful city. 

In saying that, plan your breakaway in advance and buy the skip-the-line tickets (to avoid wasting time in the queues) and you will be amazed by how much you can accomplish.

I have draft three possible itineraries.

The first one is dedicated to couples looking for a romantic and unique getaway:

  • Day 1: plan an Architecture Cruise and a walk in The Loop, the heart of Chicago
  • Day 2: visit the Driehaus Museum in the morning, and take the (in)famous Gangsters and Ghosts Tour in the afternoon

This itinerary below works great for families travelling with kids:

  • Day 1: book a family-friendly River Cruise, and spend the afternoon at the Cloud Gate and the Maggie Daley Park
  • Day 2: morning at the famous Centennial Wheel and the Children’s Museum in the afternoon

A finally an itinerary that fits so well to art and culture lovers:

  • Day 1: explore the Architecture and Design of the city taking a cruise and visiting a museum
  • Day 2: check out the Art Institute of Chicago and more venues

You can see the three Chicago Itinerary options above, detailed to morning and afternoon activities, with descriptions of all the visited places in my guide to 2 days in Chicago.

2 days in Chicago

Unique 2 days in Chicago itinerary
Unique 2 days in Chicago itinerary

More photos from the Chicago itinerary below

3 days in Chicago itinerary

A trip to Chicago for 3 days will give you a good sense of what the city is like.

Organize your itinerary ahead of time to enjoy more experiences once there.

I have draft three possible itineraries.

The first offers a romantic getaway for couples looking for an unforgettable experience:

  • Day 1: A walk in The Loop and an Architecture Cruise
  • Day 2: The Driehaus Museum and explore the underworld of Chicago Gangsters and Ghosts
  • Day 3: Explore the hidden Chicago and its off-the-radar attractions

Families traveling with kids will love this itinerary:

  • Day 1: A fun day at the Navy Pier with the Centennial Wheel and the Children’s Museum
  • Day 2: The interactive Field Museum in the morning and spend the afternoon at Museum Campus
  • Day 3: Take a family-friendly River Cruise and visit the Maggie Daley Park

Finally, an itinerary that is so appealing to culture and art lovers:

  • Day 1: All about Chicago Architecture 
  • Day 2: The Art Institute of Chicago, Tiffany Dome and some Jazz in the night at the most iconic Chicago venue
  • Day 3: Design Museum and Writers Museum

I have written a detailed guide to a 3 days Chicago Itinerary that you should read.

It includes all you need to know for the trip, with morning and afternoon activities for the above drafted itineraries, a description of all the destinations and also tips on bars, restaurants and hotels.

3 days in Chicago

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

More photos from the Chicago itinerary below

4 or 5 days in Chicago itinerary

You can accomplish so much more in four or five days in Chicago.

And you won’t have to cram too many attractions into one day.

Ideally, this is the best length to visit the Windy City in a more relaxed way, or just to see it all, if you are full of energy.

I have drafted below 3 great itinerary options that work well for a wide range of travellers.

I marked the 5th day as optional. You can bypass it or swap it if you are 4 days in Chicago

One of the itineraries is geared toward couples looking for a romantic and unique escape:

  • Day 1: The Loop & Architecture Cruise
  • Day 2: Driehaus Museum, Gangsters and Ghosts
  • Day 3: The hidden Chicago
  • Day 4: Food culture in Chicago
  • Day 5 (optional): Bike ride to Sweden (true, no mistakes)

The following itinerary is ideal for families travelling with children:

  • Day 1: Centennial Wheel & Children’s Museum
  • Day 2: Field Museum and Maggie Daley Park
  • Day 3: River Cruise and Museum Campus
  • Day 4: A visit to the zoo
  • Day 5 (optional): A lake Michigan Cruise

This itinerary is perfect for art and culture lovers:

  • Day 1: Chicago Architecture
  • Day 2: Art Institute of Chicago, Tiffany Dome and Jazz
  • Day 3: Design & Writers Museum
  • Day 4: The Loop walk and
  • Day 5 (optional): WNDR and Photography

Check my exhaustive guide to 4 or 5 days in Chicago, which includes all you need to know about the visited places, morning and afternoon activities and handy maps

4 or 5 days in Chicago

Unique 4 or 5 days Chicago itinerary
Unique 4 or 5 days Chicago itinerary

More photos from the Chicago itinerary below

7 days in Chicago itinerary

With 7 days in Chicago, you will have plenty of time to explore beyond the downtown area of Chicago.

Here is a map of the city, including interesting neighborhoods as Wicker Park or McCormick Place and Chinatown

Best areas to stay in Chicago
Best areas to stay in Chicago

If you are travelling with kids, I suggest taking inspiration from my 5 days in Chicago for families

  • Day 1: Centennial Wheel & Children’s Museum
  • Day 2: Field Museum and Maggie Daley Park
  • Day 3: River Cruise and Museum Campus
  • Day 4: A visit to the zoo
  • Day 5: A lake Michigan Cruise

and add the following 2 days:

  • Day 6: Day Trip to Libertyville. This is a small village with a great country feeling. It is just one hour by train away but it really seems another world
  • Day 7 (in summer): Rent a car and spend one day at the Coral Cove Water Park. It’s only 40 minutes from the city, or around 30 miles, and your kids will absolutely love it!
  • Day 7 (in winter): Take the Underground Donut Tour, repaired from the cold weather, or visit the LEGOLAND Discovery Center.

For an adults-only trip, I would suggest the following itinerary inspired by my 5 days in Chicago for couples and art lovers

  • Day 1: The Loop walk & Architecture Cruise
  • Day 2: Driehaus Museum, Gangsters and Ghosts
  • Day 3: The hidden Chicago
  • Day 4: Food culture in Chicago
  • Day 5: Bike ride to Sweden
  • Day 6: Design & Writers Museum
  • Day 7: Art Institute of Chicago, Tiffany Dome and Jazz night

Here below are another 3 interesting tours you may want to check out:

Best accommodations for a Chicago itinerary

Here below I have listed few accommodation options that you can check out for your stay in Chicago

For every hotel and Airbnb/Apartment I have also highlighted the neighborhood (you can read more on the best areas to stay in Chicago)

For couples:

For families with kids

For a fashionable stay 

Photos from the Chicago itinerary

Chicago downtown city skyline
Chicago downtown city skyline
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
Tiffany dome in the Cultural Center
Tiffany dome in the Cultural Center
Iconic DuSable bridge on Michigan Ave
Iconic DuSable Bridge on Michigan Ave
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
Navy Pier in Chicago
Navy Pier in Chicago
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 Millennium Park in winter with the ice skating rink
The Millennium Park in winter with the ice skating rink
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.

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