I recently visited Chicago for the first time and fell. in. love.
This trip was partially a birthday trip to celebrate my turning 23 (omg. I am old.) and also an excuse for my parents to see Pearl Jam in concert for the 589th time. I also got to hang out with two of my fave college friends while I was there! (Hannah lives in Chicago and Marie happened to be visiting at the same time.)
So to be honest, any time I go on vacation, I am typically ready to go home by day 3 because I’m a grade A homebody. Like I’m the most grandma-ish 23 year old you’ll meet. BUT I was in Chicago for almost a week and still wasn’t ready to come home at the end! I genuinely loved it and cannot wait to go back. Below I’m sharing where we stayed, where we ate, and what we did!
^^Is this not the most extra photo you’ve ever seen? Someone stop me, plz.
Where to Stay in Chicago
We stayed at the Omni Chicago Hotel and I cannot say enough good things about it! I’m a pretty picky person when it comes to hotels, because I feel like a lot of hotels are just blah. But the Omni has a super luxe vibe (without feeling stuffy) and is located on Michigan Avenue aka The Magnificent Mile, this is where ya want to be… trust me kiddos.
My mom and stepdad had actually stayed at the Omni the last time they visited Chicago, and they liked it enough to stay there again. I think that says a lot when people want to return to the same hotel!
So the Omni Chicago Hotel is an all-suite hotel. This means every room has a sitting room area, which is sooo helpful when you have 4 people in a room! I don’t know about y’all, but my family needs room to breathe, haha. I also have to point out that the beds were incredibly comfy! I slept super solid while in Chicago.
We had a Premium Suite with two double beds. There was also a sleeper sofa, so you could sleep 6 people in there easily if you needed to! We also had a work desk, wet bar, and flat screens in both the living area and bedroom area. It felt like a little apartment and there was enough space for all 4 of us. Like I said, I didn’t want to leave!
**image courtesy of Omni**
^^Sipping on rosé at Cindy’s Rooftop
Where to Eat (or Drink) in Chicago
Fig & Olive: This restaurant was probably my favorite place we ate in Chicago! I loved the whole atmosphere, menu, everything. We got crostinis, french toast, avocado toast, and salmon. It was all soooo good, I’m wishing I was eating there now! I recommend requesting a table by the big gorgeous windows so you can look out over Oak Street while you eat and sip.
Cindy’s Rooftop: This place was recommended the most! I wish we would have gone for brunch, but we went at an awkward time of day when the kitchen was closed, so we got some rosé and a chocolate board… yes, a chocolate board! As my friend Shelby put it, it’s “the most Karli thing ever” HA. This place also has an awesome view of Millennium Park, so it’s great to go here before or after your visit to The Bean.
The Happy Camper: Ok this place was SO fun! I made sure we went on Sunday at 1:30 because that’s when they have “F*ing Bingo.” It was essentially a day bar with lots of good food. Their ‘main’ food is pizza but they had so many good things to choose from! This is definitely a place to go if you love a fun, young atmosphere (and I recommend Sunday bingo if you like free shots!)
676 Restaurant & Bar: This restaurant is located within the hotel we stayed at (Omni Chicago) and has the BEST breakfast buffet. I’m not a huge buffet person normally, and when my parents couldn’t stop raving about the breakfast buffet from their last time there, I was like ok calm down it’s just breakfast. But I was in actual heaven (I know, dramatic, whatever). So many pastries and fruits and meats and, ugh, I just loved it! I think I ate like three Nutella croissants in 1 minute flat. #classy
Portillo’s: I was told this was a “classic tourist place” so we went just to say we did! They are famous for their hot dogs apparently, but we just got a milkshake and a piece of cake with ice cream. It was a nice sweet treat for a late night in the city! If any of you guys ever go and try the infamous hot dogs, let me know if they are worth the hype!
Beatrix: To be completely honest, I don’t remember any of us being blown away by the food at Beatrix. It had been a really long day so we may have all just been tired at that point, but I just know that I don’t even remember what I got there, so it clearly didn’t rock my socks off. However, the drinks were bomb. The bartender kind of made up his own concoction based on what we said we liked, and they were so good! (P.S. There’s a few different Beatrix locations, and we went to the Streeterville location – which is good if you want to walk to some fun bars after!)
To sum it up… I liked a lot of the places we ate in Chicago, but my favorite is a tie between Fig & Olive and Happy Camper!
^^At a fun pop-up exhibit called The Happy Place!
What to Do in Chicago
The Bean: Ok, duh! This is a classic Chicago landmark, formally known as Cloud Gate, located in Millennium Park. You have to be a typical tourist and take a selfie in the reflection!
The Skydeck in Willis Tower: On the 103rd floor of the Willis Tower, there’s a skydeck where you get a killer view of Chicago! It’s basically a few glass boxes that protrude off the side of the skyscraper and you can step out on to it, snap a photo, and take in the view. I recommend going after 1pm because that’s when people say the lines are shorter.
The Happy Place: I hate even mentioning this super fun pop-up exhibit because it’s now moving to Toronto! But it was essentially an interactive, walk-through exhibit with rooms full of fun and happy things. There was a giant ball pit, an upside down room, a gumball machine wall, and so many more fun things that make you feel like a kid again. To see more of it, check out the “Chicago” story highlight on my Instagram!
Architectural Boat Tour: This was my favorite thing we did! I 100% recommend doing this when you visit Chicago. It was a two-story boat (with a bar downstairs) and you got to take in all the beautiful buildings along the river. We went at nighttime which made it feel so magical! There’s a few different companies that offer boat tours in Chicago, but we used this one: Chicago’s First Lady Cruises.
There were a million other things I wanted to do in Chicago, and I hope I can go back soon to explore even more that Chi has to offer! But my first trip was so much fun and definitely made me fall in love with the city.
If you have any more questions about Chicago or our trip, feel free to comment below or email me!