The Windy City, Chi-town, City by the Lake- these are just a few awesome nicknames of Chicago. This fabulous city is where Sam was born and claims Chicago as his hometown. He loves all things Chicago – especially the sports!
We visited Chicago in February; I know we tend to explore northern places in the winter (NYC, Canada, you get the picture). We just love the off-season prices and the limited crowds! Sam and I both love the colder weather and we always prepare with layers and drink loads of hot chocolate!
On our trip to Chicago, we were joined by my sister and her husband; we had a blast! I love it when our family is able to join us on our trips! They always seem more fun when you have family or friends around! My favorite part is how we can share experiences and create awesome memories!
Top Things To See
There are many things to do and see in Chicago. Sometimes it can just be plain overwhelming when planning a trip. No trip should ever be stressful or complicated. I have narrowed it down to the top things you should see and do in Chicago to help with your planning! I also, give you a three-day itinerary, if you only have a limited amount of time. After reading through this guide you will know exactly what you want to do in Chicago.
Day 1 In Chicago
Shedd Aquarium
Because we went in the winter; we choose a few places indoors to explore. Our first stop was the aquarium. This is one of the best aquariums in the US; it is huge! Aquariums are some of my favorite places to visit. I love watching and learning about all the different kinds of animals and their different environments. I highly recommend buying tickets in advance, as this does fill up fast (and you do not want to be stuck waiting in line all day). It is on the pricier side, but like I said this place is huge, you could literally spend the entire day there, so it is well worth the money.
Sears Tower
The Sears Tower (now renamed the Willis Tower) stands 1,450 feet with 110 stories. When it was completed in 1973, it was the tallest building in the world and held that title for 25 years. Now it is considered the second-tallest building in the US and the Western hemisphere (next to the rebuilt World Trade Center). Also, it is the 16th -tallest in the world.
You must visit this tower when you are in Chicago! Not only is it a Chicago icon, but also, I guarantee you will have so much fun exploring the tower! We visited later in the evening, and by the time we got to the top, it was dark. The views of the city are just stunning!
Day 2 In Chicago
John Hancock Center
Another great skyscraper to visit in Chicago is the John Hancock Center. Sitting at 100-story and 1,128 feet it is a building you cannot miss! Right at the end of the Magnificent Mile, the John Hancock building stands as the 9th tallest building in the US.
When you visit the John Hancock Center and the 360 Chicago observation deck, you will get the best view of the entire city! Feeling adventurous? Another great activity you must try is the Tilt. The Tilt is a thrill ride that extends outward over 1,000 ft above the magnificent mile!
The Bean
Another iconic place you must visit in Chicago is Cloud Gate, more commonly known as The Bean. The sculpture was the result of an art contest, chosen from a pool of 30 other designs! The Bean is located in Millennium Park, right behind the ice-skating rink.
There are so many photo-ops with The Bean, I recommend getting there early, as it does get crowded later in the day! This goes without saying, it is free to walk around.
Millennium Park
I have added the last few spots for visiting Chicago in the summer. Of course, you are more than welcome to visit these spots in the winter, it just might not be as enjoyable in the cold weather. In the park is the above-mentioned Cloud Gate, and there is also a fantastic McCormick Tribune Plaza and Ice-skating rink (open all year round). The park also has Buckingham Fountain – the most gorgeous and gigantic fountain I have seen! Unfortunately, it was not on when we visited, but I am hoping to see it whenever we go back in the summer!
Day 3 In Chicago
Magnificent Mile
The Magnificent Mile is currently Chicago’s largest shopping district; it has a variety of shops, from mid-range to high-end stores. It is not only a shopping center, but also has restaurants, museums, and hotels! This is a great way to spend the afternoon! Be on the lookout for some of the more famous buildings; such as the Chicago Water Tower and the Wrigley Building!
There is a lot more you can do besides shop and go to museums. You can take a river cruise down the Chicago river, you can choose between having dinner on a luxury yacht, or the comfort of the Spirit of Chicago. There is also a bus tour through the city, or you can try your luck at one of the several escape rooms around the city!
Navy Pier
The Navy Pier is one of the best places to visit, in the summertime of course. It is open year-round, but keep in mind that it is subject to change. There is no admission fee to get on the Pier, but there are other attractions on the Pier that may charge a fee. So, what is there to do on the Navy Pier; there are loads of yummy food options to try! If you love amusement parks, there is the carousel, the Ferris wheel, and remote-control boats! There are even more shops and a movie theater!
Best Places To Eat
There are so many wonderful restaurants in Chicago, it was hard to narrow down our favorites! There are a variety of restaurants to choose from: they have all American, Italian, and many hotdog stands.
Giordano’s
Chicago is most famous for its deep-dish pizza – my personal favorite. After a full day of exploring and walking in the cold, we were starving! Believe me when I say this is the best pizza you will ever eat in your life! I know I am being dramatic, but seriously, this was so delicious! We ordered their breadsticks as well, and they were gone in literally one minute. If you go to any restaurant in Chicago, let it be Giordano’s!
I hope you enjoyed reading this travel guide for Chicago! It was such a fun city to explore! We would love to come back and visit in the summer!
If you have any specific questions about visiting Chicago please be sure to leave a comment below or contact us!
Until the next destination!
Check out our DC Travel Guide!
Interested in a road trip through Oregon? Check this out!
18 Comments
gerry
March 13, 2019 at 6:04 pmThis is a really good piece. This gives me an idea of how I could spend my weekends. This is awesome.
Emily and Sam
April 2, 2019 at 11:18 amYes, it is such a great weekend trip!
Hayley
March 13, 2019 at 7:34 pmChicago looks very cool. I’m not big on aquariums or that sort of thing but I would love to see the Navy pier – that looks beautiful. The magnificent mile also looks very cool!
Emily and Sam
April 2, 2019 at 11:19 amYes, the Navy Pier is such a fun place to visit (in the summer of course).
Viktoria
March 13, 2019 at 11:02 pmI’ve never ever heard of that pizza place before, but as a lover of a thin and crisp crust, I’m not sure if I’d enjoy this pizza variation – have you been to Italy? The pizzas there are superb!
Emily and Sam
March 15, 2019 at 1:53 amNo, we haven’t been yet, but would love to! Can’t wait to try their pizza!
jin
March 14, 2019 at 1:11 amAwesome list for first timers for sure! I was in Chicago back in 2006 and have def hit up every single place that you’ve mentioned. But as I have mentioned before, these are must see places if it’s your first time – highly recommend.
Emily and Sam
March 15, 2019 at 1:53 amNice!! It is such a fun city!
Albína Mrázová
March 14, 2019 at 11:11 amWhat an amazing post, especially for first timers! I always feel kinda lost in big American cities, so this should help me out once I will head to Chicago
Emily and Sam
March 15, 2019 at 1:56 amYay!! That’s so exciting!
Brianna
March 14, 2019 at 2:28 pmGreat post for first-time visitors to Chicago! The pizza would be worth the trip alone, it looks so yummy. I didn’t realize Chicago had an aquarium, that would likely be my first stop too!
Emily and Sam
March 15, 2019 at 1:56 amRight?! We want to go back just for the pizza lol
Rachel Silverwood
March 14, 2019 at 6:05 pmChicago looks amazing! I love the look of all the architecture and skyscrapers, but standing on that glass floor at Sears Tower would be a no from me haha
Emily and Sam
March 15, 2019 at 1:57 amhaha yeah, I couldn’t stand on there for long 🙂
Mikaela Ferguson
March 14, 2019 at 6:29 pmI loved Chicago when I was there. The streets downtown are so wide and colourful and green compared to New York. I was there for work so I didn’t get to do any of these activities. Thanks for the post!!
Emily and Sam
April 2, 2019 at 11:20 amAgreed, it is more green and open compared to New York City, but just as busy and fun!
Dylan
March 15, 2019 at 2:18 amGood on you for heading to northern places during the winter! My mom and I used to head to Chicago every December before Christmas but the tradition only listed for a couple years before the cold got to us. And then, after five years of living there, I still never made it to some of the spots you’ve listed! Maybe I should schedule a return visit…though hopefully not in the winter 😉
Emily and Sam
April 2, 2019 at 11:21 amOoh, I bet it is lovely around Christmas time!