What I did:
Many people consider Chicago to be at or near the top of the list of comedic hubs in the world. Many famous comedians got their start doing improv comedy in Chicago, and many more come to Chicago with the hopes of becoming the next big thing. Two of the most famous improv shows in Chicago are Second City (which Saturday Night Live grew out of) and IO. IO was formerly called "Improv Olympics, but was supposedly shortened to IO to avoid copyright infringement with the International Olympic Committee. IO offered well priced shows that can be a good way to spend a couple hours, and possibly see the next big star on their way up.
Free Walking Tour-
Free walking tours are a great way to see a city. The hostel I was staying in offered one leaving directly from the hostel lobby. Although it only runs once a week, it was an excellent tour. Also, I made some new friends on the tour.
Millennium Park is one of the top places to visit on a trip to Chicago. The Cloud Gate, more commonly known as "The Bean," is located inside the park. The park, which is free to enter, also contains gardens, an outdoor concert venue, and impressive fountains on 24.5 acres of lake front property.
Lincoln Park Zoo-
Lincoln Park Zoo is one of the oldest zoos in the United States as well as one of the few free zoos in the world. The zoo is using its facility to plan sustainable populations, reinvigorate populations on the verge of extinction, enhance animal health, and understand animal behavior. They have a wide selection of impressive animals on site.
360 Chicago Observation Deck (John Hancock Observatory)-
The 360 Chicago Observation Deck, formerly known as the John Hancock Observatory, offers great views of Chicago from its 94 story high vantage point. They also offer something called "Tilt" that, for an extra charge, lets you enter a glass box that slightly tilts over the edge of the building. However, it did not tilt as much as I expected. I would recommend going to the Signature Lounge on the 96th floor of the building and getting a drink or a snack as opposed to paying to go to the Observation Deck.
Wrigley Field is one of the most historic stadiums in the United States. Home to the Chicago Cubs, it has been open for over a century. I did not have the opportunity to go to a game while I was there, but I was able to see the iconic stadium.
Skydeck Chicago Willis Tower (Sears Tower)-
The Skydeck Chicago at the Willis Tower offers some great views of the city. More commonly known as the Sears Tower, it is the highest observation deck in the United States at 103 stories high. They also have glass boxes known as "The Ledge" that extend out from the building and offer some amazing views. While there is usually a line to enter the boxes, there is no charge to do so (unlike the "Tilt" at the 360 Chicago Observation Deck).
The Chicago Riverwalk is a great place to walk along when the weather is nice. There are also a number of bars and restaurants located along the walk.
Buckingham Fountain is a large fountain located in Grant Park near the waterfront of Lake Michigan. There are some great views looking towards the lake, and there are also some great views looking back at the city's skyline. At night, lights will accompany the fountain adding some cool effects.
The Crown Fountain features two large screens facing each other, with a face on each screen. Actual water will occasionally "spit" out of the mouths.
The Navy Pier is an area with a variety of restaurants and attractions such as a ferris wheel and a merry go round. Although it is somewhat of a tourist trap, it is worth checking out at least once.
North Avenue Beach-
Although there is no ocean near Illinois, Chicago does have some beaches on the coast of Lake Michigan. North Avenue Beach was a relatively nice beach, and there is a train nearby for walking, biking, or running.
Carlson Gracie Jiu Jitsu-
Carlson Gracie Jiu Jitsu school was very cool and welcoming. Everyone I met there was incredibly nice, and it was a great place to train.
Lake View YMCA Chicago-
The Lake View YMCA was a nice place to workout while I was in Chicago. It had everything I needed to get a great workout in, and the staff was very nice.
The French Market in Chicago had a number of different food vendors. It is not the best market I have ever been to, but it is worth stopping by and trying some food if you are in the area.
Where I ate and drank:
Chicago is famous for its deep dish style pizza. Giordano's is one of the places in the discussion for the best pizza places in Chicago, and depending on who you talk to it is at the top of the list. It was very good and worth trying.
Billy Goat Tavern-
The Billy Goat Tavern has been open in Chicago since 1934. It is a fun, local place with a cool environment. The food is not particularly tasty or healthy, but it is worth stopping by if you are in the area.
Ipsento Coffee is an excellent coffee shop in Chicago. They have a couple locations with different feels to them. The best cup of coffee I have had in Chicago was the nitro coffee I had at Ipsento.
Three Dots and a Dash-
Three Dots and a Dash is a tropical themed speakeasy in Chicago. The drinks were very good and served in fun cups.
Bordel is a speakeasy located inside the Black Bull restaurant. The drinks were excellent, and the place was set up in the throwback/speakeasy style.
Broken Shaker is an excellent craft cocktail bar located inside the Freehand Hostel. Their quality is on par with their sister bar in Miami, which has received numerous awards.
The Signature Lounge-
The Signature Lounge is located on the 96th floor of the John Hancock Center. I would suggest going here and ordering a drink or a snack over paying to go to the 360 Chicago (John Hancock Observatory). It costs less, you get something to eat or drink, and the view is actually two floors higher.
Cindy's is a rooftop bar located above the Chicago Athletic Hotel. I overlooks Millennium Park, Lake Michigan, and the Art Institute of Chicago. The drinks are good and the view is great.
Intelligentsia Coffee and Tea is a coffee company based out of Chicago. Their coffee is sold throughout the USA. Although they do not have nitro coffee, they do offer some good coffee options.
Tempo Cafe is a nice place to get good food at late (or early) hours when other options are not open.
Haymarket Pub and Brewery-
Haymarket Pub and Brewery was a nice place to grab a drink while waiting for a table at The Little Goat nearby. They also have a variety of TVs that show a number of sporting events.
The Little Goat-
I had wanted to visit the Girl & the Goat, but it was not open when I had the opportunity to go there. However, The Little Goat is their sister restaurant, and it is located close by. The food there was excellent. I would gladly go back again, although next time I would be interested in trying the flagship restaurant.
The Drifter is a speakeasy located inside The Green Door bar behind a set of bookshelves. It is a fun, interesting little place with some high quality drinks.
Longman & Eagle-
Longman & Eagle is an excellent bar and restaurant serving high quality food and drink for reasonable prices. They also have a small hotel connected to the restaurant.
Clark Street Ale House-
Clark Street Ale House is a very good bar with a nice selection of craft beer. Their sign offers those passing by to "stop and drink," and I found the place very welcoming.
Szechuan Cuisine is a very good restaurant in Chicago's Chinatown.
Wildberry Cafe is a very good breakfast place in Chicago. They offer some healthy choices as well as some options to satisfy a sweet tooth.
Topo Gigio is a very good Italian restaurant located in Old Town Chicago.
Beatrix is a great restaurant with a few locations in Chicago. They offer a nitro coffee as well as a bulletproof coffee. I would like to go back to Beatrix to try some items off of their interesting food menu.
Portillo's Hot Dogs-
Portillo's is a famous Chicago hot dog and sandwich chain. I had their famous Italian beef sandwich dipped in gravy. It was not the healthiest thing I have eaten, but it was very tasty.
Green Mill Cocktail Lounge-
I was slightly disappointed by the Green Mill Cocktail Lounge. I have had the opportunity to visit some amazing speakeasies throughout the world, and Green Mill Cocktail Lounge was an actual speakeasy during prohibition that was frequented by Al Capone himself. However, the quality was not as high as some of the other speakeasies I have visited.
Spilt Milk is an excellent bar in Chicago. The drinks and service were excellent. I would recommend checking it out, and I plan on going back next time I am in Chicago again.
Watershed Bar is located beneath Pops for Champagne. They have a nice selection of craft beers and high quality cocktails.
Where I stayed:
Freehand Chicago is part of the Freehand hostel chain that also has locations in Miami and Los Angeles. It is located right by the Magnificent Mile, which is an area with a variety of different shops. They are somewhat of a hotel/hostel hybrid. While they don't have quite the environment that some other hostels have, they do have very good facilities such as comfortable beds and even a small workout room. They also have an award winning hostel bar, and a quality breakfast cafe.
How I got around:
I used Chicago public transit system to get around. Their train system is very good, and extends all the way out to O'Hare airport. It was also the filming location for Wanted, starring Angelina Jolie and James McAvoy.
My favorite thing:
Chicago has a lot of good things to offer, making it hard to pick one favorite thing. There is plenty of good food, drink, and entertainment to be found throughout the city.
My least favorite thing:
The biggest downside to Chicago is their weather for the majority of the year. It is a great place to be in the summer, but the conditions can be brutally harsh for much of the year. Also, some of their bars and restaurants have strict dress codes, requiring men to wear a suit, tie, and dress shoes, and women to wear a fancy dress and fancy dress shoes.
For next time:
Next time I would like to try more of Chicago's food, and visit a show at Second City. I would also like to visit Smoque BBQ, Deadbolt, the Violet Hour, the Library, and the Bassment.
My name is Billy. I am a personal trainer and teacher. I love traveling, and wanted to share some of my experiences. I hope to inspire you to see, taste, and experience more of the world. Feel free to take some of my recommendations for your own travels. I also blog about health and fitness at CustomizeMyWorkout.com/blog