Top 5 Things To Do In Chicago

January 15, 2019

Chicago is a great city to explore in the Midwest. From eating the best deep dish pizza “Chicago-Style”, to the interesting architecture, to boat tours through the city (literally), there are endless amazing things to do in and around Chicago. Here are my top 5 things to do in Chicago.


1) Order a “cheezborger” from the Billy Goat Tavern

Off of E Lake St is where you will find the famous Billy Goat Tavern where “cheezborger, cheezborger! No fries, chips! No Pepsi, Coke!” catchfrase originated from in January of 1978 on SNL, starring Bill Murry.

We started off our visit in the Windy City by deciding the first place to have a meal. What other way to start off the weekend by eating at the famous Billy Goat Tavern? After filling our stomaches, we had a little history class with one of the workers behind the bar.

Come to find out, the tavern was introduced in 1934 when Greek immigrant, William “Billy Goat” Sianis, wrote a check out to purchase the Lincoln Tavern for $205. After the check was¬†bounced, it was later repaid with sales from the first weekend. Sianis eventually was known as “Billy Goat”, after a goat fell off of a passing truck and wandered inside. He eventually adopted the goat, grew a goatee, earned the name “Billy Goat” and changed the name of the pub to Billy Goat Tavern.


2) Architecture River Cruise

Just a 7 minute walk or 3 minute car ride towards the Chicago River from Billy Goat Tavern, you can easily snatch a ride on the Architecture River Cruise.

Personally, I would highly recommend taking this breathtaking tour through the city as it allows you to see Chicago through a rare and amazing perspective. The Architecture River Cruise is a 2 level boat tour that runs more than 20 times a day from the Navy Pier to Michigan Avenue.

With the tour lasting about an hour, you will discover the major events that helped shape the architectural history of Chicago. If you have an eye for this stuff like myself, the 40+ buildings, including the Wrigley Building and Sears Tower, will capture your mind like no other and if you thought it could not get any better, it does. The expert on this Chicago architecture adds a personal touch that leaves you wanting more.


3) Eat some “Chicago-Style” pizza

After shopping on Michigan Avenue, head over towards N State St and try out the #4 ranked pizza place in the nation, (aka Oprah’s favorite pizza in Chicago) Pizano’s Pizza & Pasta.¬†One of the most welcoming environments I’ve been to this day with a servicing of the best deep dish pizza.

Or if you’re a fan of Oprah, this pizza place is her favorite. Try her highly recommended thin crust pizza. To be quite honest, I couldn’t decide between the deep dish and thin crust. Maybe it was because I was sidetracked by the Holly and Little Rudy’s Chocolate Chip Cookie. The cookie is a freshly baked chocolate chip cookie prepared in a pizza pan with a layer of vanilla ice cream, chocolate syrup, and whipped cream. TO DIE FOR !


4) 103rd floor of Willis Tower

This is a definite “must see” on your future endeavor to the Windy City. It is located in the Willis Tower (also known as the Sears Tower) at 1,353 feet above Chicago’s surface. This building has the highest observation deck in the US with a 360 degree view of the city below you. You have the capability of seeing up to 50 miles out and 4 different states!

If you’re an adrenaline junky and heights don’t bother you, there is something special for people like you. There is a glass balcony extending four feet outside the 103rd floor of the Willis Tower, be prepared for both a thrilling experience and a wait to get out to the ledge; people love this part of Chicago.


5) Millennium Park

Located just southeast of the Navy Pier and north of the Art Institute of Chicago, lies Millennium Park. Whether you’re a nature lover, art enthusiast, or seeking for the best place to take selfies with you pals, Millennium Park is the kind of place you can spend an entire day in.

Depending on the time of year you head out to Chicago, look up and check out the following locations:


If you do not do at least stops 1-4 that I listed above, (as weather doesn’t matter here) I highly recommend eating lunch in the plaza at Park Grill.

Also, located across the street from the park is the Chicago Cultural Center where you can find a calendar-packed schedule of events and free things to do. Definitely worth the visit.