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2 Days in Chicago Itinerary

Chicago is a city that is very different than any other in the United States. Chicago has a variety of things to do that are perfect for anyone. 3 Days in Chicago may not be enough, but I’ve highlighted some of my favorite things to do and some that are uncommon. Chicago has a bit of a past which makes it a very interesting place to visit. This itinerary is perfect for a weekend in Chicago or just 2 Days in Chicago. There are so many free things to see and do which makes it all worthwhile.

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2 Days in Chicago | What to see in Chicago in 2 days

A little bit of history about Chicago, there was a fire called the Great Fire of Chicago that occurred on October 10, 1871, that caused the entire city to burn down. There is a rumor that a woman’s cow had kicked a candle and started burning the barn down on the southwest side of the town. The fire started to spread quickly and yet the firefighters assumed the fire wouldn’t get very far. Many people assumed the fire wouldn’t hop the river and yet it did kill 100 people. The fire ended up spreading like wildfire burning the entire city down.

As you will notice when you visit the city of Chicago, there will be no buildings in the city made of wood. Mostly because they were burned down but also because there was a law that did not allow for wood buildings within the city because of how devastating the fire was.

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Where to Stay in Chicago for 2 days

There are a lot of places to stay in Chicago, but honestly, it depends on what you want to see and what you want to do. You can easily stay in the city and be close to everything. I usually have a tendency to stay in Logan Square which can be a bit more affordable and have more culture for young adults. There are a lot of murals, places for coffee and beer around.

Although, staying in Logan Square may be good if you have a car or don’t mind taking public transportation.

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Where to Eat in Chicago during your 2 Days

There are plenty of great restaurants in Chicago. You can enjoy some of the best deep dish pizzas, markets, bakeries and more!

  • Eataly
  • The Girl and the Goat
  • Portillo’s
  • Lou Malnati’s or Giordano’s
  • Passerotto
  • Parachute
  • Lula’s Cafe
  • The Elephant & the Castle
  • Goddess Bakery

2 Days in Chicago: Day 1

This would probably be the best way on how to spend a Saturday in Chicago. If you only have one day, I highly suggest you do this Day 1 Itinerary in Chicago, even if you happen to be a local. It’s a great way to see some places you may have not seen before.

Goddess Bakery | 2 Days in Chicago

Quick Breakfast at Goddess Bakery

Goddess Bakery is a great place to get a quick bite and some delicious coffee. They have a cute atmosphere with neon signs, beautifully designed cookies, and pastries and close to a lot of the downtown action. This Bakery is within walking distance to the bean making it the perfect first location to visit before taking a stroll in millennium park or cloud gate.

The Bean | 2 Days in Chicago

Visit the Bean and Millennium Park – Best thing to do in 2 days in Chicago

The most popular thing to do in Chicago is the famous bean at Millennium Park. The bean, also known as cloud gate, is an art piece made by Anish Kapoor. This piece was made for the millennium, aka the year 2000. However, the piece was not finished until 2005. This piece has now become a famous landmark for Chicago bringing in thousands of visitors each year.

2 Days in Chicago

Take a FREE tour of Chicago with Chicago Greeter – How to visit Chicago Cheap

This is probably the most underrated thing to do in Chicago! I have never heard of it until I started researching something to do in Chicago. Since I have already been to Chicago once before so I wanted to see some new things. I stumbled about the Chicago Greeter and this was a great surprise. I highly recommend taking a tour with Chicago Greeter and hope you get Susan as your tour guide. She is very informative of the city and provided the best tour the city.

2 Days in Chicago

Enjoy Lunch at Eataly

Eataly was recommended by our guide Susan and it is definitely the place to visit and eat. There are so many fresh ingredients here and lots of delicious choices. Additionally, it is a great way to get some appetizers, wine and enjoy some small chat with friends. We enjoyed our bruschetta and cheese options.

Portillo's | 2 Days in Chicago

Go to Portillo’s Hot Dogs for a Chocolate Cake Ice Cream Shake

Portillo’s is a famous place to eat in Chicago. They are known for their delicious hot dogs but additionally their famous chocolate cake and chocolate cake ice cream shake. This place is pretty big and there are plenty of food options. It is a must place to try some great food.

Visit the Art Institute of Chicago

Chicago is known for its art especially with the Millennial Park and the famous Bean. Because of this, you have to make a pit stop to the art institute of Chicago. There are several famous pieces in there such as Andy Warhol’s Marilyn Monroe piece and other places as well.

Eat Deep Dish Pizza at Lou Malnati’s or Giordano’s

You can not visit Chicago without eating the most famous Chicago pizza. Furthermore, there are two main Chicago pizza places in the city. Lou Malnati’s or Giordano’s. The locals will definitely tell you that Lou Malnati’s is the best place for Chicago pizza. Honestly, I just found the two pizzas completely different and I loved both of them. It was hard for me to choose since we had two different kinds of pizzas. I suggest you try and make time to try both and make the decision for yourself!

2 Days in Chicago: Day 2

Grab Breakfast at Hash Chicago

Hash Chicago is a great place to grab breakfast. This place fills up pretty quickly on the weekends, but what is great is that you can either take your order to go. If you love potatoes, this place is a great place to get some delicious potatoes and plenty of food. FYI, their waffles with cookie buttercream are absolutely delicious and hard to stop eating!

2 Days in Chicago

Take a Photo at the Famous Mural Behind the Concert Music Hall

A great contribution to Robin Williams and as the genie from Aaladin. He will be a great missed and this is a great tribute to all that he has done. This mural by far is one of the most beautiful within the city and a must visit for those who love his work.

2 Days in Chicago

Take a photo at the Famous Chicago Mural

This is the iconic Chicago Mural that is worth visiting and fairly self-explanatory for those Instagram photos.

The Garfield Conservatory | 2 Days in Chicago
The Garfield Conservatory | 2 Days in Chicago

Visit the Garfield Park Conservatory for FREE

Conservatory and Bio-domes are my favorite places to visit. They are absolutely stunning and is a great way to experience nature even in the coldest and wettest of days. The Garfield Park Conservatory is definitely a must visit especially if you have kids or just to take some time strolling through an array of beautiful trees and plants.

Frank Lloyd Wright's House | 2 Days in Chicago
Frank Lloyd Wright's House | 2 Days in Chicago

Take a tour of Frank Lloyd Wright’s home and studio

If you love art and architecture, you can’t miss out on Frank Lloyd Wright’s home. He was a famous architect in the United State who loved to create new and innovative architecture. Frank Lloyd Wright wanted to create his own style rather than obsess over old styles like the Victorian era. He was asked many of times to create Victorian-style architecture, but it was the one he hated most. His innovation is what made his work original. Frank Lloyd Wright focused more on geometrical shapes, straight lines and simplicity.

Cub's Game | 2 Days in Chicago

A Cubs Game is a must for Chicago Itinerary for 2 days

Wrigley Field is a famous field of when Babe Ruth did his famous arm out into the outfield. This field was built in 1914 and is the second oldest field in the United States. Now, you don’t have to go to a Cub’s game, you can also choose to do a stadium tour.

If you are looking to build a 3 days in Chicago Itinerary, I suggest you add an Architecture Cruise along the river, spend a day shopping in downtown Chicago, and visit the 360 Chicago to get the best view of the city.

There you have it, my 2 days in Chicago post.

2 Days in Chicago Itinerary 1

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