Top Things to do and Attractions in Chicago Illinois!

2bearbear @ The Bean (aka Cloud Gate) Chicago
2bearbear @ The Bean (aka Cloud Gate) Chicago
There are so many things to do and attractions in Chicago Illinois! Having arrived in Chicago via the Amtrak California Zephyr, we’ve explored the city and here are some top picks from our travels!

Things to do in Chicago Illinois

Millenium Park

On the east side of the city, you’ll find a stretch of park that includes the Millenium Park and Grant Park. Here, you’ll be able to visit The Bean (aka Cloud Gate), Jay Pritzker Pavilion and the Buckingham Fountain.

2bearbear @ The Bean (aka Cloud Gate) Chicago
2bearbear @ The Bean (aka Cloud Gate) Chicago
The Bean aka Cloud Gate - Most Iconic Structure in Chicago
The Bean aka Cloud Gate – Most Iconic Structure in Chicago
Jay Pritzker Pavilion - Free Open Air Concerts
Jay Pritzker Pavilion – Free Open Air Concerts
Panoramic Buckingham Fountain Chicago
Panoramic Buckingham Fountain Chicago

When one thinks about structures in Chicago, it is usually synonymous with The Bean (Cloud Gate). But it is hard to imagine that the public sculpture was only completed in 2006 after a competition held in 1999 – won by Indian-born British artist, Anish Kapoor. Today, one will say that you have not been to Chicago if you have not see The Bean.

The Jay Pritzker Pavilion (next to Cloud Gate) is an open-air performance stage. During our visit, we were able to watch the Grant Park Orchestra perform live. Surprised that such high quality performance would be available to the public for free. Of course, many came ready with their picnic mats, sandwiches and drinks for a day out on the lawn.

Address: 201 E Randolph St, Chicago, IL 60602

Chicago Illinois Attractions

Oak Street Beach Chicago

Oak Street Beach Chicago
Oak Street Beach Chicago

Like any other beach, Oak Street Beach offers beach volleyball, jog/cycle track and of course a great spot for sun tan lovers. But the greatest difference? The beaches of Chicago is formed by one of the largest fresh water lake in the world – Lake Michigan!

Address: Oak Street Beach 1000 N Lake Shore Dr

The Second City Comedy & Improvs

The Second City Chicago
The Second City Chicago
Old Town Chicago
Old Town Chicago

Kate arranged for us to visit The Second City during our visit to Chicago. The Second City is a comedy club that also offers improv classes. Famous alumni of The Second City includes Tina Fey, Steve Carell, Stephen Colbert and Bill Murray. If you’re not familiar with improvs, it is a genre of comedy where improv actors improvise on stage based on the props, lines available to create jokes. One of the most famous of these is the show “Whose Line Is It Anyway”. We had a great time at the show and even took away a 20oz souvenir glass for $13. The price includes The Second City glass (packed separately for you so you won’t have to bring back a sticky beer glass) as well as a choice of beer. Close by is the Chicago Old Town. As with many Old Towns in USA, you’ll find restaurants, pubs and bars that line the streets.

Address: 1616 N Wells St, Chicago, IL 60614
Opening Hours: 10am to 9pm

United Center – Home of the Chicago Bulls

Thanks to Kate, Tom got to visit United Center – Home of the Chicago Bulls. This is also where you’ll be able to take photos with the famous Michael Jordan statue at Gate 4 of United Center!

Tom @ United Center Chicago - Home of the Chicago Bulls
Tom @ United Center Chicago – Home of the Chicago Bulls
Tom with Chicago Bulls Legend - Michael Jordan Statue
Tom with Chicago Bulls Legend – Michael Jordan Statue

Address: 1901 W Madison St, Chicago, IL 60612

What to eat in Chicago Illinois

If you’re travelling to Chicago, food will definitely be part of your itinerary. There’s so many famous foods such as deep dish pizza, hot dogs, steaks and even donuts! That is why we have dedicated an entire post to cover Where to Eat in Chicago Illinois. But here, you’ll catch a glimpse of these delicious grubs!

Numero Uno Deep Dish Pizza - Pizzeria Due Chicago
Numero Uno Deep Dish Pizza – Pizzeria Due Chicago
Portillo's dipped sandwich & milk shake
Portillo’s dipped sandwich & milk shake
HUGE Carrot Cake @ Gibsons Bar & Steakhouse
HUGE Carrot Cake @ Gibsons Bar & Steakhouse

Other Things to do and Attractions in Chicago Illinois

There are actually so many other things to do and attractions in Chicago. You can check out the magnificent mile – shopping street of Chicago

Magnificent Mile - Shopping Street of Chicago
Magnificent Mile – Shopping Street of Chicago

take a cruise along the Chicago River to view beautiful architectures…

Architecture Cruise along Chicago River
Architecture Cruise along Chicago River

enjoy a night out at the Navy Pier (restaurants, amusement park for the kids)

2bearbear @ Navy Pier Chicago
2bearbear @ Navy Pier Chicago

Or sample some asian fare at Chicago’s Chinatown

2bearbear @ Chicago Chinatown
2bearbear @ Chicago Chinatown

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Where to stay in Chicago Illinois

During our visit to Chicago, we stayed at The Buckingham Hotel. Definitely a place that you can consider for your next visit to Chicago. Located on the 40th story of the Chicago Stock Exchange Building, it offers amazing views of the Chicago skyline and even allows guests to visit the Buckingham Club for gym, sauna, swimming pool and jacuzzi facilities!

We hope you have enjoyed our review of the Top Things to do in Chicago and have a fantastic time on your next visit to the Windy City!

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