North America, United States, Ilinois

Only have 3 days in Chicago? This is what you need to do!

We have a guide for you for any short stop multi-city trip

Chicago, also known as the windy city, is the 3rd most populated city of the United States. The town, located on the shores of Lake Michigan, in the northeast of Illinois state. Chicago is famous for its architecture, skyscrapers and world-class museums that attract visitors all over the world. Even though many travellers often overlook the city, it is an ideal stopover for a multi-city flight plan.

A gentle snow began to fell as I walked up State Street. I try to avoid cliché shots as a budding photographer, but the mood was too good to pass up.
Chicago

Best things to do in Chicago


No matter how short your Chicago stayover, you should not skip these attractions as they are some of the best experiences Chicago has to offer.

  1. Millennium Park
The Bean
"The Bean" in Millennium Park

Millennium park is a must-see on any Chicago itinerary, no matter how short your stopover mainly due to many famous landmarks. The cloud gate, aka "The Bean," is the most iconic attraction. "The Bean" is a bean-shaped structure made with silver, which perfectly reflects the city and surrounding buildings. Taking pictures reflected on the fabric is a famous Instagram shot. The Jay Pritzker Pavilion, The Lurie Garden and the BP pedestrian bridge are other excellent attractions of the millennium park.

  1. Willis Tower

Willis tower is the most famous skyscraper and the observation deck of Chicago and was the tallest building in the world for almost 25 years. A glass balcony on the 103rd floor, known as "the ledge," allows you to look straight down for a fantastic view of the city. The tower opens at 10 am and stays open until 10 pm. Tickets cost around $25 for adults and $17 for children

Willis Tower
  1. Navy Pier

It is on the shoreline of Lake Michigan, and it is one of the best places to visit as it has something for everyone. Restaurants, lake tours, bike rides, museums, and theatres are some of the few activities that will keep you occupied. The most popular attraction is the giant Ferris wheel known as the centennial wheel. If you visit Chicago during the end of May or August, witness the amazing fireworks shows host at Navy pier.

Photo by Josh Howard / Unsplash

Best places to eat and drink in Chicago

Chicago has a few world-famous interpretations of classic comfort food. One particular recipe is Chicago deep-dish pizza. The pizza, stuffed with many layers of cheese and cooked in a deep pan, which is the reason behind the name, deep-dish pizza. One of the best places to have a deep-dish pizza is Giordano's.

Giordano Pizza

Adventuring millennial blog and Nomandasaurus blog both believe Giordano's serves the most delicious deep-dish pizza. The next is the Chicago hot dog, an all-beef dog on a sesame seed bun served with attitude. Nomandasaurus blog once again said Portillo's have the best Chicago style hot dogs.

Portillos Hotdogs

Best neighbourhoods to visit in Chicago.

Neighbourhoods of Chicago are distinct from each other and have their own culture. Out of the many, these are the few best neighbourhoods worth visiting during your Chicago stayover.

  1. Lincoln park

Lincoln Park is the best neighbourhood for the nature lover. Lincoln park zoo, located in the middle of the park is free to visit. Lincoln park conservatory, Nature boardwalk, and Theater on the lake are some other best places to visit in Lincoln Park.

An absolutely breathtaking sunset in Chicago's famous Lincoln Park Zoo. This is one of the best views of the entire city! It was a Friday evening and I remember starting to see an incredible sunset forming, so I grabbed my camera, hopped on a bus and headed straight to Lincoln Park. I setup on the bridge right when I arrived and patiently waited, but I never though I would capture the incredible purple streak across the sky!
Lincoln Park
  1. West loop

West Loop is Chicago's foodie's spot. A former industrial zone now is a dining and nightlife hotspot with many restaurants and bars. Take a stroll on Randolph street, also known as restaurant row, where you will find many high-end restaurants to street food joints.

Fog Over Chicago
Photo by Erol Ahmed / Unsplash
  1. Hyde park

Hyde Park's neighbourhood has so much history. It was the site of 1893 Chicago's world fair. The University of Chicago and the Museum of science and industry are the two most significant places in Hyde Park.

Off the beaten trail in Chicago

There are few places and things many visitors often overlook, but still worth a visit.

  1. Riverwalk and cruise

Take a stroll alongside the river. It is a 1.25-mile walk filled with bars and cafés. If you want to be more adventurous, you can rent a bike or kayak and while you are there, hop on to a cruise to explore more sights of Chicago.

Shot at the location where Wacker Drive bends near State Street. The Tump Tower and Jewelers Building are seen.
River Walk
  1. Medieval times dinner and tournament

It is the medieval-themed restaurant built like a castle with polished armour and artifacts. You can enjoy a full course meal while being entertained by the fantastic displays of horsemen and knights

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Cheers to the weekend!

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Medieval times dinner
  1. Bahá'í temple

This temple is not technically in Chicago. You have to take a 22-mile journey to Wilmette to visit this temple. It is one of only eight worship places of the Bahá'í religion in the world.

Bahá'í temple

Best museums to visit in Chicago.

Chicago has many museums and art galleries to visit. Among them, these are the best to visit, in my opinion.

  1. Art Institute of Chicago

Chicago art museum is the second largest in the country. It is home to many impressive collections from all over the world from ancient Japanese arts to portraits from the Byzantine empire. The museum opens from 10.30 am to 5.00 pm daily, and a general ticket will cost $25.

Art Institute of Chicago

2.  Museum of science and industry

This museum, dedicated to science and industrial exhibits. Among them is a replica of a coal mine, German submarine captured during world war one and a module of Apollo 8 spaceship. It operates from 9.30 am to 4.00 pm daily.

Museum of science and industry

3.  Adler planetarium

This museum is all about astronomy and astrophysics. It has three theatres, an observatory with an aperture telescope and a collection of print materials. There are several ticket options priced at $19 to $50, and it opens from 9.00 am to 4.00 pm daily.

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🤔 Will a black hole take you to another universe? What is a particle accelerator? Is the universe really "expanding"? 🌌 You have space questions, we have answers! Adler astronomers 💛 answering your questions. 🔭 Read our latest Adler 'Scope Blog (link in our Blog Instagram Story Highlight) and continue asking us questions by tagging #AskAdler on social media. #AdlerFanFeature[ 📷: Bill Chiu ] ____________________ #spaceblog #stargazing #eyesontheskies #universe #backyardastronomy #astrophotography #amaeurastronomy #adlerplanet #adlerplanetarium #spaceviews #spaceisfreakingawesome #chicagomuseum #chicagomuseumcampus #fullmoon #fullmoons #museumcampus #chicagoskyline #chicagohistory

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Adler planetarium

Travel Itineraries.

It is vital to have an excellent itinerary to make the most out of your stopover in a multi-city flight plan. Check out the following itineraries as guidance.

24 hours in Chicago.

You need to make the most out of 24 hours for a memorable stayover in Chicago. Stephanie shares her 24-hour adventure in Adventuring Millennial, which covers the best experiences the city has to offer.

Check out Stephanie's adventure here,

How to Spend 1 Day in Chicago- The Adventuring Millennial
Planning a trip to the windy city? Do you only have 24 hours? Check out our 1 Day in Chicago itinerary to plan your perfect trip.

2 days in Chicago.

Lizzie and Dave are a couple, travel all over the world to mix with different cultures. In their blog wanderlust and life, they shared an itinerary that also covers other essential details like weather and accommodations.

Find out how to make the most out of Chicago in 2 days here,

A 2 day Chicago itinerary to help you make the most of your weekend in the city | Wanderlust And Life
If you are looking to spend 2 days in Chicago then checkout our guide to the best tourist attractions. For our weekend in Chicago we enjoyed some amazing food and visited the best sights. This is our 2 day Chicago itinerary to help you plan your own trip.

3 days in Chicago

Alesha and Jarryd are Australian natives that have been travelling since 2008. Their objective is to encourage others to visit by sharing their adventures on the blog Nomandasaurus. They have shared an in detailed description of the places, hotels, and restaurants in the city.

Check out this 3-day itinerary of Chicago here,

The Perfect 3 Days in Chicago Itinerary (2020 Edition) | NOMADasaurus Adventure Travel Blog
Headed to the Windy City and wondering what to do? Read this jam-packed itinerary guide to a perfect 3 days in Chicago to make the best of a short trip there!


4 days in Chicago

The more time you have to spend more experiences you can have. Kiyoko is a Japanese traveller who shares her knowledge and honest opinions on her blog, footsteps of a dreamer. She shares her experiences in getting around the city, things to carry and many more in the blog.

Read her 4-day Chicago adventure here,

Chicago 4 Day Itinerary: A Long Weekend in Chicago, Illinois, USA | Footsteps of a Dreamer
Considering a long weekend in Chicago, Illinois, USA? There is so much to do or see, where do you possibly begin? If you’ve got a few days to spend traveling, check out this 4-day Chicago itinerary!
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About Doug Creighton

Data Scientist in Toronto in the tech industry. I have travelled to 40 countries and used to build handcrafted stopovers. Built this algorithm years ago for me and finally got it online for everyone.
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