Let’s say you have less than 48 hours to spend in Chicago, IL. Where do you go and what do you do? It’s tough to try to pack in alllll the sights and activities in such a short amount of time, so planning your trip ahead of time is crucial in order to get the most out of your weekend. No need to stress about planning – I’ve got your Chicago Weekend Travel Guide covered!
Friday
I arrived in The Windy City on Friday after work. The flight from Charlotte to Chicago is only about an hour and twenty minutes – not bad at all! Plus, with the hour time difference, I ended up landing around 5:45pm CST time. I found my way to the train (not sure what the locals call it, so I might be sounding like a total tourist LOL. But, uhhhh… you know….. the Chicago train) and headed straight for Wicker Park.
Our first stop in Chi Town was to grab a quick bite to eat. We walked to the most delicious burger place called Small Cheval that had a line that went out the door. It was SO good – seriously one of the best burgers I’ve ever had in my life! The menu is extremely small. They only have three items on the food menu – not kidding. The menu consists of: cheeseburger, hamburger, and fries. BOOM, that’s it. I ordered a cheeseburger and fries, and it was amazing.
bodysuit | shorts | shoes | sunnies | bag | belt
From there, we stopped by The Royal Palms on our walk home. This bar is seriously adorable and is truly an Instagrammers paradise. The concept is that the entire bar is essentially a giant shuffleboard. How cool is that? On top of the huge shuffleboard concept, there were tons of other awesome photo opps throughout the entire place. In fact, there were so many places to take photos that I didn’t even end up taking a picture in the bar because I couldn’t decide on a place to take one. I got overwhlemed and we left, ha! I guess I’ll just have to go back.
We then went to The Cabana Club, which is up on the 6th floor of The Robey Chicago. This bar is also, in my opinion, an Instagrammers paradise. There were tons of tropical drinks on the menu (hello, Red Bull slushy and 64-ounce frozen margarita), and – get this – there’s even a pool in the middle of the patio outside. Maybe I’m sheltered, but I’ve never been to a bar that has a pool inside it before. SO cool. We went at night time, but I would love to go back and visit The Cabana Club to see what it’s like during the day. I bet the pool and city views are amazing!
Saturday
On Saturday, we started our day with brunch at The Hampton Social. Again, this place is another Instagrammers paradise (can you tell what trend I was going for on my trip?). On top of the many photo opps (Rose All Day sign, which I unfortunately didn’t snag a picture of because there was a private party in the way), the food was AMAZING!!! I ordered the crab and avocado toast, which was served on sourdough bread and topped with burrata and an over easy egg. The cocktails were delicious too – they’re well known for their froze. The froze is served with Tito’s handmade vodka, proverbs rose, and peach puree. It was very sweet, in my opinion, but still delicious and definitely worth trying it out.
From there, we did tons of walking around. Chicago is an absolutely stunning city, and after visiting, I can certainly see why people would want to live there. On top of the gorgeous city views, the weather could not have been better while I was there. There was not a cloud in the sky, and it was a perfect 75 degrees outside. We walked along the riverwalk, and past the Chicago Theater, eventually making our way to Londonhouse Chicago rooftop bar. I ordered a glass of rose and we sat up on the rooftop for about an hour or so. The view of the city is incredible from the LH Rooftop, and I 10/10 recommend going here if you’re visiting Chicago any time soon.
After finishing our drinks at the LH Rooftop, we made our way to one of the most popular tourist attractions in Chicago – THE BEAN! I had been relentless about seeing The Bean all weekend, and even during the weeks leading up to my trip. It would be an absolute sin to visit Chicago and not at least stop by to see it, right? Obviously, the entire population of Chicago had the same idea as me. The Bean was jam packed with tourists, as you can see from my photos. People were EVERYWHERE, all trying to get the same perfect Instagram shot. I’m definitely happy I was able to check The Bean off of my bucket list – it had been there for way too long!
From The Bean, we did some more walking around before heading home to get ready for dinner. We ate some delicious sushi at Yuzu, which was absolutely delicious and one of the coolest sushi restaraunts I’ve ever been to! Check out how this sushi roll was decorated. I mean… what?! SO cool. From sushi, we headed to a bar called Machine, which was, of course, also awesome. I ordered the “Hey, Smash Me” drink which consists of: lemon hangar 1 vodka, riesling, honey, lemon, greek yogurt, lemon candy. The cocktail is served with a mini gold hammer that is used to break the ice in order to drink the cocktail. The concept is awesome in itself, and the drink tasted amazing too. I wanted to try every drink on the menu!
Sunday
On Sunday, we finally got DEEP DISH PIZZA! I had been wanting to try some real Chicago deep dish pizza for soooo long, and I refused to leave Chicago without trying it. There are tons of deep dish pizza restaurants in Chicago, but we went to Pequod’s and it certainly did not disappoint. I’m craving it again right now just typing this out. Did you know you can order frozen deep dish pizzas and have them delivered to you anywhere in the US? Just a little fun fact for you.
From Pequod’s, I packed up my bags and it was already time for me to head back to the airport! Only having less than 48 hours in a city makes it nearly impossible to do everything you want to do or see everything you want to see. There were tons of places on my Chicago bucket list that I didn’t end up being able to go to. Those places include but are not limited to:
- Visit The Sky Deck Chicago
- Go to a Cubs game
- Visit the aquarium
- Deep dish pizza at Lou Malnatis
- Eat a Chicago hot dog (we actually did eat one, but I want to try one from a Cubs game!)
- See a show at the Chicago Theater
- Take a ride on a boat cruise or water taxi
…and that’s just to name a few! Do you have any other Chicago recommendations for the next time I visit? I would love to hear your recommendations, if so! Please leave them in the comments below, and I’ll be sure to add them to my list of sights to see the next time I visit the Windy City.
xo,
Ashlen
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