City Guides, North America
Leave a Comment

Chicago, Illinois

On December 16th I left my college behind and ventured on to ‘the windy city’. I’m going to be honest, I didn’t know much about Chicago, just that it was the third largest city in the US and that the famous ‘bean’ was there. But sometimes going to a place with little or no expectations means you enjoy it just that bit more. Filled with a lot of gangster history, some of the first skyscrapers in the world and a love for jazz music, this city has something for everyone. I loved exploring this city and all it has to offer.


I traveled with a close friend I met at TCNJ, and we found so much more to do than we first thought.

Where I stayed:

HI Hostel – Downtown Chicago

This was the only hostel that was really downtown so we didn’t mind paying a little extra. The hostel was big enough for elevators (hooray for people like me who have heavy suitcases) and had one of the biggest common areas I have ever seen for a hostel. The rooms were also very spacious and it was one of the most comfortable beds I have stayed on so far. You got the usual freebies; breakfast, towels etc. But this hostel also had several free walking tours, a free hot dog night, free outings to comedy clubs and jazz bars and a bar crawl as well as free beer before those events. I would definitely recommend staying here.

What I did:

Cloud Gate

DSCN5161 DSCN5374

Well…. The Bean, because no one actually calls it that. The one thing I was super excited for did not disappoint. The reflection of the city and walking underneath it was an amazing thing to see. Some people threw their hats up inside it to see where it actually starts, and go check it out at night for a whole new experience. I could have stared at it for hours.

Willis Tower (Sears Tower)

DSCN5262 DSCN5261

The 110 story tower is a must whilst in Chicago. When it was completed in 1973, it was the tallest building in the world for 25 years. As of 2013, it stood as the second tallest building in the US and eighth in the world. The views are incredible as you look over downtown, the surrounding suburbs and as far as the eye can see over Lake Michigan.

The Skydeck

DSCN5269  DSCN5265

The Skydeck sits on the edge of the 103rd floor of the Willis Tower. It is kind of terrifying, but exciting. Cool photo opps!

Millennium Park


Great views of the Chicago skyline and a cute park for a walk (upgrades to the children’s playground are underway).

Shop & walk down the Magnificent Mile

DSCN5223  DSCN5228

North Michigan Avenue, or the Magnificent Mile is the shopping capital of the city. Right in the heart of downtown, it has everything from Tiffany & Co. to Forever 21. The street in itself is a beautiful walk, especially around Christmas time (above photos).

The Riverwalk

DSCN5237 DSCN5243

The Chicago River, running straight through the center of the city is a wonder to walk beside. The city is in the midst of upgrading the walk and adding more sections for 2015 visitors, so be sure to check it out.

Architecture Walking tour

DSCN5093 DSCN5101

Chicago Cultural Center

DSCN5143 DSCN5146

This free Chicago Cultural Center often hosts free shows for the public, including this classical music one I attended on a Wednesday at around 12pm. The building in itself is beautiful, with a huge glass dome roof. A must for any architect lovers.

Famous Jazz Bars


Chicago’s jazz scene is world famous, and the Green Mill was made famous by gangster Al Capone. He was a regular there, and I sat one booth over from where he would sit many years ago.

Head out in Logan Square

1441387_10152765114619270_4776430970611837547_n  10806208_10152765113689270_7879841299225641205_n

Chicago is fairly spread out, with a lot of residential areas close to the city. Logan Square and especially North Milwaukee Street is one area filled with bars and clubs to head out to. We did a bar crawl here and one of the stops was the Emporium Arcade Bar (above, left) which was a huge bar filled with.. you guessed it, arcade games and pool tables. It was a lot of fun before we headed to a few more bars and a club in the area.

We ventured to Big Joe’s in Logan Square one night to witness the famous turtle race (above, right). Get there early and get raffle tickets for every drink you buy and then see if you’ll be drawn to be the lucky owner of a racing turtle in the next heat. Exciting stuff!

The Lincoln Park Zoo Zoolights

DSCN5366  DSCN5370

As we were there just before Christmas, the Zoo put on their annual light show and it was an amazing experience. The shows across the park were fun, festive and a must see. The Zoo in itself is okay, but I was very disheartened by how sad most of the animals looked having very small enclosures and I never saw one zoo keeper the whole visit. The lion was pacing back and forth and looked so depressed, then actually roared. It was a cry for help and just broke my heart.

Chicago was a delight to visit. There was so much I didn’t get a chance to do including a ‘gangster tour’ which visited many places that had a special significance in the old gangster wars. I also wanted to check out cool neighborhoods such as Wicker Park and Hype Park but I guess that will have to wait until my next visit..

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s