The first couple of months that Jenn and I were together, we were on a huge traveling kick. I remember I was planning a trip, trying to figure out where we should go next and I brought up Chicago. To say the least, Jenn wasn’t thrilled. “What’s in Chicago?” she asked. So I did the research. We went. And guess what happened?
We ended up having the best time. So good, in fact, that we decided if we were ever going to be forced to move to a downtown city in America for whatever reason (we prefer the burbs), that we would choose Chicago. There was so much to do and see in such a small radius, everything was extremely accessible by foot- not need for public transit or Ubering. The food was simple, comforting, and delicious, and the architecture of the buildings in the city made us both really appreciate unique building architecture- something I, personally, had never really cared about prior to this trip.
Finally, there was plenty do in Chicago on a budget. Jenn is usually decently frugal (although becoming less frugal as time goes on since I tend to want a lot…), so saving money for her is always a welcome opportunity. From taking a walk along the lake (free) to getting discounts at already affordable attractions using a city pass, there was plenty to do that was well within our means.
Before I start listing off some great things you can do when paying a visit to Chicago (all of which also count as more reasons why we’d move to Chicago), I highly recommend getting either the Chicago City Pass or the Go Chicago Pass. The benefits differ between the cards and whether one or the other might be more beneficial to you is based on how many in your party are going and how long you’ll be staying, so be sure to do you research before defaulting to one or the other. Whichever one you choose, both passes provide great savings benefits on some awesome attractions- many of which are mentioned below!
Let’s get started!
Things to Do in Chicago
Get a Chicago Dog and, of course, a deep dish pizza.
Starting off strong! The Chicago Dog (a hotdog topped with yellow mustard, onions, bright green relish, tomato wedges, and a very large dill pickle spear) and the deep dish pizza are classic staples that you pretty much mandatory to try when in town. If you didn’t, did you really experience Chicago to the fullest? Probably not.
We got our hotdogs from Devil Dogs on the South Loop, and our pizza from Giordano’s on the Central Loop. Both equally as exceptional, delicious, and just the taste of Chicago we were looking for.
As an added bonus, since Jenn and I were in town during Valentine’s Day weekend, we had the pleasure of eating a heart-shaped Chicago deep-dish pizza. So romantic.
Check out the museum campus.
Shedd aquarium
This aquarium houses all the classics- sharks, penguins, stingrays whose backs you can run your hands across. Our favorite area was the Wild Reef Exhibit. As soon as you step foot into the exhibit, you can hear the crashing waves of their Wild Reef’s tidal habitat and you’re instantly immersed into an oceanic wonderland.
Adler planetarium (It’s bigger than it looks!)
This planetarium doesn’t look like much from the outside, but once you step inside and take a look around you’re likely to be taken aback by how it seems to go on and on. From the vibrantly colored Welcome Gallery, to the Mission Moon exhibit where you can take a look into a historic spacecraft, to the many immersive planetarium shows to choose from, there’s definitely plenty here for for anyone who shares a love for space exploration and history.
Field Museum
Life-size animal taxidermy displays, Egyptian mummies and sarcophagi, and Sue the T. Rex are just the beginning of this impressive museum. We walked the place for hours without experiencing an ounce of boredom. There was so much to see- it just kept going and going! One main factor that staved off boredom was the variety– did I mention this place houses dinosaur bones AND real-ass mummies? Crazy.
Also: I’m not sure if it’s still there, but there was this hilarious and random mini virtual reality ride right in the middle of the museum somewhere on one of the upper floors, akin to something you’d find in the middle of a mall. Jenn and I decided to give it a try because really, why not? It actually ended up being really fun! It’s based on an underwater adventure, and it’s just as corny as it sounds. Definitely would recommend.
Brave standing over the Chicago streets in a Clear Observation Box at Skydeck Chicago
Unfortunately when Jenn and I went to visit the Skydeck it was too cloudy to see anything- as soon as we got to the place where you get tickets the workers informed us that it would basically be like standing in a big glass room surrounded by nothing but white… We still went anyway since our ticket guaranteed free admission.
Although it was true that the room was surrounded by thick fog, it somehow did not make it any less scary standing in that little glass box hundreds of feet over the streets of Chicago. So if you’re seeking a small thrill and some great views (provided it’s not cloudy), this is a great place to check out.
Get a stunning view of the Chicago lights at Chicago 360– at night.
Although the observation deck Chicago 360 is open during both the day and the night, we decided to go at night. We’re glad that we did, as we got a really unique and stunning view of the Chicago lights which went on for miles, that you can’t quite get during the daylight hours.
Another thing we appreciated about this observation deck was the tech. They have informative panels that you can easily interact with to help you learn even more about what you’re seeing 94 floors above Chicago city.
If you’re seeking thrills here too, you can choose to pay a little extra to experience TILT, in which you step into a glass box before they literally tilt you forward until you’re face to face at an alarming angle with an over 1000 foot drop down to Michigan Avenue. Note that you can get a discounted rate for tickets with the CityPass!
Hit up the Big Bean.
Just like Chicago deep dish, when you’re visiting Chicago you are obligated by the universe to visit the Cloud Gate statue- or more commonly known as the ‘Big Bean’.
The practical significance of Cloud Gate, conceptualized by Anish Kapoor and completed in 2005, lies in the architectural process as many of the ideas for construction were thought to be impossible based on the size, weight, and materials. The artistic significance lies in Kapoor’s desire to convey certain themes such as ambiguity, attempting to give the viewer a sense of ‘in-between’. This is more apparent in the unique reflections the structure gives off of the surrounding skyline and passerby’s, which is the main draw.
Be sure to get plenty of pictures when you go, and definitely try some different angles. Heads up though, there will be some people who will offer to take your picture for you and then proceed to charge you. Don’t accept anyone’s offer to do this unless you specifically request an obviously pedestrian passerby yourself, or you may find yourself in a bit of an awkward position when you inevitably cannot pay with cash- which is the only way they’ll take payment.
Take a walk along frozen Lake Michigan (if you’re visiting during the winter season).
As mentioned earlier, Jenn and I visited Chicago during Valentine’s Day weekend- that is, during the Winter months. Thankfully for us, the first couple of days spent in town were pretty mild. The last couple of days, however, were bitterly cold.
We were obviously not as comfortable during these days as we would have been if it were, say, during the warmer Summer months. But one perk of it being freezing cold was that parts of Lake Michigan were actually frozen too- but not completely. It was quite a unique sight to see, up close, Lake Michigan shifting ice back and forth in its tides among water that was not yet frozen. We got an up close view of this, as you can see above, while taking a stroll along the path that led up to the Museum Campus.
Grab coffee at one of Chicago’s many coffee shops.
Latte 
The Iron Man Scrambler
If you’re ‘jonesing for a cup of joe’ (and maybe even a snack), there’s no shortage of coffee shops just a Google search away around Chicago that provide good coffee, pastries, and even breakfast.
Shortly after our arrival in the city, we visited a little place called Goddess and the Baker at Millenium Park. We got a couple lattes and some breakfast food. All of it fresh, comforting, and a lovely warm welcome to the Windy City.
Bonus round!
Go on a dinner cruise on Lake Michigan.
The main draw of our trip to Chicago centered around the big event- a dinner cruise on Odyssey Lake Michigan that Jenn gifted to me for Valentine’s Day. She chose to keep it a surprise all the way up until we boarded the ship, and it was the perfect night out. A full course dinner, a DJ playing romantic tunes throughout the night, breathtaking night views of the city skyline across the Lake, and a complimentary surprise to cap out the night, all made the night a perfectly romantic one.
If you’re in town for Valentine’s Day, or even just for fun (they do cruises all year round), and you can afford to splurge a bit, we both definitely recommend the Odyssey Lake Michigan dinner cruise as a fun, unique, and romantic experience!