Winters in Chicago are brutal. I thought that New York had it rough, but the winters in New York do not even compare to those in the Windy City. While I thought the city was charming during those visits, I did not want to spend much time outside because of the temperature, which meant that I ended up spending most of my time indoors and I did not get to do a lot of sightseeing. They say the ‘third time is a charm’, and it was during my third trip to Chicago that I really got to know the city and appreciate all that it had to offer.
The Lakefront & Navy Pier
Lake Michigan
On the east side of Chicago, you can find the beautiful Lake Michigan. Besides being very picturesque, the Lake is a great place to go and ride a bike, relax by the water, or just sit and watch the boats pull into the harbor.
One of my favorite places to relax by Lake Michigan was at the harbor directly across from the Buckingham Fountain. Another wonderful place to enjoy the Lake was from the Navy Pier.
A boat docked at the Navy Pier
In addition to the Navy Pier being an amazing place to view Lake Michigan, it is also home to a large ferris wheel, numerous places to shop, and a number of dining establishments.
Navy Pier
The Lakefront is truly a wonderful part of the city and if you are looking for additional things to do on and near Lake Michigan, check out Frugal Frolickers list of ‘The 3 Best Things to Do on the Chicago Waterfront‘.
The Skydeck & Willis Tower
The 103rd floor of the Willis Tower and Skydeck Chicago provide excellent 360° views of the city.
Not only do you have amazing views of Lake Michigan, but you can also see all of downtown Chicago and into the surrounding suburbs. The best thing to do at the top is to go out onto an encased glass ledge and literally look down at the city below you from an astounding 1,353 feet (412 meters).
Boating on the Chicago River
Cruising down the Chicago River
If cruising down a river screaming the lyrics from ‘I’m on a Boat‘ at the top of your lungs fulfills your lifelong sailing dreams, Chicago is the place to do it.
During BlogHouse I also had the opportunity to sail down the Chicago River with Chicago Electric Boat Company on a self-maneuvered boat manned by travel blogger Amber from With Husband in Tow.
If driving your own boat down a busy river does not seem appealing, you can also take one of the many boating tours that Chicago has to offer – check out this Yelp list for the best tours in the city.
Biking
Chicago’s Divvy Bike program
I love to bike around different cities and when I traveled to Chicago, I took part in the Divvy Bike program, which is similar to many shared rental bike programs across the world. I really appreciate the fact that Chicago’s infrastructure caters to bikers and there are bike lanes everywhere.
Millennium Park
Beautiful Lurie Garden
Millennium Park is absolutely gorgeous. Not only does it have the beautiful ‘Bean’ that I fell in love with, but is also home to a number of cultural events, beautiful flowers in the Lurie Garden, and an ice rink!
Millennium Park in the true Chicago architectural spirit
Buckingham Fountain
The magnificent Buckingham Fountain
Inspired by the Latona Basin at Versailles, the Buckingham Fountain, one of the largest fountains in the world, was constructed to serve as the centerpiece of Grant Park, and it does a magnificent job at it. In person it is absolutely stunning!
Street Art
Street art in Chicago’s Pilsen neighborhood
The street art scene in Chicago is phenomenal. With works from both local and international street artists, the work in Chicago is definitely a must see.
The Food
Eating a torta in Pilsen, Chicago
I could not write a post about Chicago without mentioning all of the wonderful food you can find in the city. Although I previously went into the food scene in great detail, I thought it was definitely worth mentioning one more time. With its eclectic mixture of foods ranging from Mexican to Greek to Chinese, Chicago is definitely a food scene worth checking out.
Have you been to Chicago before? What were some of your favorite things about the city?
FTC Disclosure: A special thank you to Skydeck Chicago, Chicago Electric Boats, and Divvy Bikes for the complimentary admission and rides during my stay in the city of Chicago. While I was provided with complimentary access, all opinions in this article are entirely my own.
Awww, thanks for linking to my post! Your photos are beautiful – love the shot of you on the Skydeck! 😛
You’re welcome and thanks Lindsay! 😀
Love Chicago! I have been a handful of times, but still don’t feel like I have really explored the city thoroughly. My favorite things: Linkin Park area and the free Linkin Park Zoo! I also loved the Chicago Food tour of Old Town and the Gold Coast. Aweseome history and delicious food!
I totally missed out on the food tours in Chicago, but the next time I am in the city I will have to make sure to catch one! Thanks for sharing your experience too!
Great write up. I read your street art article as well – there is some great artists work on the walls.
Hi James, thank you 🙂 The street art scene in Chicago is very wonderful!
Yay! Glad you got to experience the city in better weather. I fell in love with it soon after moving here. My faves are the huge lakefront, the great neighborhoods, & of course the amazing food.
I am too! They say the third time is a charm 😀 Thanks for sharing so much information during BH about the lovely neighborhoods, I still have a lot to explore!
Wow! The SkyDeck looks scary! Lol! These are great things to see and do – will definitely put them on our list great the next visit!
I thought it would be scary too before I went up, but surprisingly it wasn’t too bad 😀 You should definitely check it out!
I thought it would be scary too before I went up, but surprisingly it wasn’t too bad 😀 You should definitely check it out!
I swear, posts like this always remind me why I’m so obsessed with this city (especially in the summer). I’m so happy you got out to the Lurie Garden as I think it’s sometimes overlooked, yet provides a spectacular backdrop for photos. Did you make it to the cultural center. It’s free and the architecture inside and out is stunning as it’s home to an enormous Tiffany glass dome. Fun fact: it was the city’s first public library and a way to show NYC that Chicago is ‘cultured’ too 😉
Yes the Lurie garden was gorgeous, surprised there were not more people over that way.
I briefly stopped into the Cultural Center and walked to the lovely staircase in the back and saw the dome. It was lovely 🙂 Great fun fact too!