Things to do in Chicago

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Chicago, Chicago
I’ll show you around
I love it
Bet your bottom dollar you’ll lose the blues
In Chicago, Chicago

–       Frank Sinatra

The Famous Bean

It was in August, 2017 when I planned a random trip to meet an old friend. He drove all the way from Missouri and I flew up from D.C. It was just 2 short days in Chicago (weekdays at that), but that city didn’t let itself lose to us.

In here, I will be sharing an itinerary for two days with you folks wherein I will show you the best way to enjoy Chicago on weekdays while covering maximum number of major destinations of the city.

Welcome to the most American place in America!!

Chicago is second to no city. In fact, it is sometimes referred to as the Second City because too many buildings were burned down in the Chicago Fire of 1871. 

Hence, the name. The city of Jazz has a lot to offer. Lets do it!

Day: 1 

I’ll get straight to the point. It would be best if you had your hotel/Airbnb downtown or nearby. Most of the attractions are downtown. For a trip lasting two days, my first suggestion would be to buy the CHICAGO CITY PASS. This pass will leave you $100 lighter and covers a total of 5 attractions which would otherwise cost you approximately $220 in entry tickets. You end up saving $120. Doesn’t seem like a bad bargain now, does it?

This city pass will open doors to:

  1. Shedd Aquarium
  2. Skydeck Chicago
  3. The Field Museum
  4. Museum of Science and Industry OR 360 CHICAGO
  5. Adler Planetarium OR Art Institute of Chicago

Read more about City Pass HERE.

Five on our list and here we go.

This is a great shot of me flying amongst and being dwarfed by the edifices of Chicago. #ShotOnGoPro

Throw it away. Forget yesterday. We’ll make a great escape here!

–     Steve McQueen in The Great Escape (1963)

1st Stop: Art Institute of Chicago

I chose Art Institute of Chicago over Adler Planetarium because I had already visited the Samuel Oschin Planetarium (Los Angeles) and Albert Einstein Planetarium (Washington D.C.). So, skipping this didn’t feel that bad; NOT BAD AT ALL after I crossed those frightening lions at the front door of the Art Institute of Chicago.

I was all clean shaved back then

FUNFACT: The Art Institute of Chicago is one of the oldest and the largest art institutes in the United States. It is believed to receive around 1.5 million visitors annually. Even if you are not much into the arts, you can easily spend around 1-2 hours marveling at the outstanding works inside. It contains over 300,000 workpieces by famous artists like, M.F. Hussain, Georges-Pierre Seurat (He is the one with the famous painting of a Sunday afternoon including a number of Parisians at a park by the River Seine.) and also Gustave Caillebotte, who painted The Paris Street; Rainy Day. There are many other famous paintings and sculptures by renowned artists that I don’t know about.  

The Paris Street; Rainy Day by Gustave Caillebotte

There are separate areas dedicated to different types of arts like American Art, Modern Art, Indian Art, European Art, etc. There are also some departments containing the 1,544 objects in the Arthur Rubloff Paperweight Collection and the 68 Thorne Miniature Rooms – a collection of miniaturized interiors of a 1:12 scale showcasing American, European and Asian architectural & furniture styles from the Middle Ages to the 1930s (when the rooms were constructed).

One of the Thorne’s Miniature Rooms

This place surely has a lot to offer, especially if you are an art enthusiast. I am sure you wouldn’t hesitate to spend at least half of your day here.

TIP: Photography is allowed inside and it goes without saying that you are not to touch anything. Selfie Sticks are prohibited. 

Done with all the art, we have to keep moving!!!!!! Time won’t stop in the Museum, will it? We have but 2 measly days. HAHA!!

“You only get one life. It’s actually your duty to live it as fully as possible.”

–     Sam Claflin in Me Before You (2016) 

 2nd Stop: The Bean (Cloud Gate)

You won’t need your City Pass because it’s open for all. It’s the architectural wonder of Chicago: The Bean!!!

I think its nice

The Bean is situated very close to the main city. It is inside the Millennium Park where you will also encounter some other small attractions like the “Jay Pritzker Pavilion”, “Millennium Monument”, “Crown Fountain” and “Harris Theatre”. Do visit them all. You don’t want to miss anything do you?

Millennium Park

The Bean is officially known as “Cloud Gate”. (So, if you per chance want to put it into your Google Maps or something, try Cloud Gate.

FACT: Cloud Gate is a public sculpture by Indian-born British Artist Sir Anish Kapoor. So, a person coming from India (like me) obviously wouldn’t miss it (Not that you guys should.). It is truly a masterpiece and worth visiting. If you are a good photographer, you will surely get great Instagram-worthy shots. ;P . You can check mine out below.

Cloud Gate





If you are a local, you surely know about Denny’s which is a famous place for breakfast. They serve amazing pancakes and waffles. Milkshakes are good, too. Also, if you are an omelet lover, they also have some great choices for you.

Another place that I would suggest for breakfast- Lou Mitchell’s Restaurant.


“It’s a big city with a bunch of sports teams. I think people know about Chicago. “

–     Alyson Hannigan in HIMYM (2005 – 2014)

3rd Stop: Skydeck Chicago

If you are quite active on social media platforms, you must have definitely seen some videos where people go to the top floor of a building and stand on a Look-Through-Glass-Surface-Floor and you would say in your mind, “Someday”.

The center one is Skydeck Chicago

Today is the day when you would want to propose to your girlfriend standing on a glass ledge with an amazing view of the Big City. This attraction comes under your Chicago City Pass which means that you don’t need to worry about standing in a queue to wait for an elevator which will take you to the 103rd floor of this iconic structure. You just have to hop on into the next one. 😀

I mean, obviously, you have to follow the rules.


This iconic building is the tallest in the Western Hemisphere, standing at 1,450 feet and 110 stories tall, encompassing more than 4.5 million square feet, including its Skydeck and 103rd floor glass viewing platform (The Ledge), which attracts more than 1.7 million (more than the Art Museum) visitors every year. It ranks eighth on the list of tallest buildings in the world.

The Ledge transforms how visitors experience Chicago. At 1,353 feet above the ground, The Ledge’s glass boxes extend out 4.3 feet from the skyscraper’s Skydeck on the 103rd floor, providing never-before-seen views of the city. You can also get your pictures clicked professionally by the Skydeck authority and then purchase them later at the counter on your way out by the gift shop. It is a little expensive though. As far as I remember, it costs up to 40$ for one photo. 

They also give you and your friend time to click pictures with your own devices for a couple of minutes. Make sure you don’t spend too much time on The Ledge as there will be a long queue behind you waiting for their turn.


I am sure you don’t want to get frowned upon and/or cursed.

Below attached is my photo from the Glass Ledge.

P.S.: That ass-face wearing red is my friend. 😛
You can also do THIS on the ledge (like my friend did). I would never even dare to try this 1500 feet above the ground!! NEVERRR!!!

By now, it will almost be evening and most of the attractions that are left will be closed at this time. But hold on a second, you are in Chicago and your night cannot get any better when you have amazing clubs and discos all around.

I went to “Smart Bar” & “Berlin” (Yup, I went bar-hopping).

These two are one of the best clubs in town and I assure you that you will have a great time here. We confirmed with our hosts from Airbnb about them and they are indeed the best.

We are going to leave the rest of the attractions for tomorrow. Till then, PARTY HARD or GO HOME!!!! 😀

TIP: If you are a foreigner, you could try HOOTERS (if you haven’t tried it yet). You must have heard about this place and why it got famous. 😜

Plus, it serves amazing Chicken Wings!!!

I don’t want to travel too much, I just want to travel, because time just gets away from us.  

–     Anonymous 

Day: 2


If this is the question troubling you early in the morning, then my suggestion would be to pack your bag and get ready for the upcoming adventures of our day in Chicago because you have got no other option.

I have a Scottish friend who consumes alcohol like it was water and yet, he shows up to work every day as if nothing had happened. So, just be a little braver, get up and get going.

4th Spot: 360 CHICAGO

This skyscraper is quite similar to Skydeck Chicago but more adventurous. Formerly known as the John Hancock Observatory, it lets you enjoy 360° views from 1000 feet above Lake Michigan and Chicago’s famous Magnificent Mile. The most amazing part of this floor is that they have recently introduced a feature known as TILT.

View from the Skydeck

In short, THE OBSERVATION DECK TILTS DOWNWARDS FROM THE 94TH STOREY (YUP, THAT’S RIGHHTTTTT!!!!), offering a downward panorama. The attraction, which costs $5 to tourists and is thought to be the first of its kind, holds up to eight people, with the platform slowly moving outward to an adventurous angle above the Windy City.

This attraction is also included in your Chicago City Pass but you will have to pay a few dollars extra for the TILT.

View from the deck

We are now left with only 2 of our main 6 attractions which are included in the Chicago City Pass. Ladies and gentlemen, we are now headed to The Field Museum.

This is GOLD.

5th Spot: The Field Museum

Easter Island Head: Hey! Dum-dum!

Larry: Yes?

Easter Island Head: You give me gum-gum!

Larry: I give you gum-gum?

Easter Island Head: You new Dum-dum. You give me gum-gum.

Larry: Gee, okay, you know what? I have no gum-gum. Sorry. And my name isn’t Dum-dum. My name’s Larry.

Easter Island Head: No, your name Dum-dum.

Easter Island Head: Oh, you in trouble, Dum-dum. You better run-run. From Attila the Hun-hun.

Easter Island Head: See you later, Dum-dum!

–     Night at the Museum (2006)

You don’t need to be a film buff to be familiar with these dialogues. There is no way on Earth you haven’t heard this before. Allow me to introduce to you The Field Museum, The Museum of Natural History.

Here, it is going to be the closest you will ever come to living with a Dinosaur. The Field Museum combines the research of its world-renowned scientific staff with its award-winning design expertise to create high-quality travelling exhibitions. It has almost everything related to history, like The Animal Exhibitions, The Grainger Hall of Gems, Inside Ancient Egypt, Evolving Planet, The Ancient America, etc.

As soon as you enter, you will encounter the skeleton of a T-Rex (Tyrannosaurus Rex), just like in the movie.

FACT: This T-Rex is known as the “Sue, The Tyrannosaurus Rex” and is the best-preserved T-Rex fossil yet discovered. It is at least 67 million years old. This T-Rex was 28 years old when it died. This fossil was named after the person who discovered it, Sue Hendrickson.

“Sue, The Tyrannosaurus Rex”

You can easily spend 2-4 hours in there. Don’t miss out on watching some great 3D-4D short movies which are all very knowledgeable and so much fun to watch. I watched one of Sir David Attenborough’s.

P.S.: I LOVE Sir David Attenborough!

Before going to your next stop, you might want to try Kim & Carlo’s Chicago Style Hot Dogs. It is a very popular place to have hot dogs! It is quite near to where you currently are. Just turn on G.P.S. and you will find it in a jiffy. They serve some really nice and succulent hot dogs. I liked them a lot.


If you are ready to go a little off the route, try Little Branch Café which is just 10 minutes by foot from the museum.

6th Spot: Shedd Aquarium (Just 5 minutes walk from The Field Museum)

It is an indoor public aquarium which is more than 85 years old. It was at some point of time the largest indoor aquarium in the world.

It contains several exhibits like Waters of the World, Caribbean Reef, Amazon Rising, Wild Reef, Oceanarium, etc. It also contains a 4-D Theatre which is not to be missed. Trust me on this. Films shown here include Coastal Predators, Sea Monsters, SpongeBob SquarePants, Planet Earth, Ice Age, Dora the Explorer, Rudolph The Red Nosed Reindeer (seasonal), and the Polar Express (seasonal).

I am a supporter of Sand Cloud Organization and the mission they serve is to save the fish. Hence, I didn’t go inside; instead, my friend did. I will be sharing with you some pictures that he took.


Our mission is to SAVE Marine Life! If you want to join our movement, simply fill out the form below! We look forward to hearing from you 🙂

Join our team, save the fish. We would love to have you with us.

With this, our 2 AWESOME days in Chicago end. I really loved the city. Also, I wanted to visit Chicago since the day I came to know that Frank Sinatra was born here. It’s just his kind of town.

That is the Big Windy City- Chicago.

P.S.: It is not an advertisement or an attempt to promote Chicago City Pass or Sand Cloud Organization. I just feel that Chicago City Pass is undoubtedly the best way to enjoy all the great attractions of Chicago. Trust me, after taking advantage of it, you will be singing the same song. 😛

I wish you a great time in Chicago.
Thank You!

“There is no real ending. It’s just the place where you stop the story.”

–     Frank Herbert.



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of the day

“In desperate need of a full body massage,

4 days of sleep and a ticket to the Bahamas. “

– Anonymous