I’ve never been shy of my love for Chicago, especially Chicago in the summertime. And while I’m lucky enough to work downtown {and live close by in Lincoln Park} I rarely have a good excuse to play tourist in my own city and explore the more well-known places and spaces in Chicago. But once every few years I decide to go all out and explore downtown – finding new favorite places and re-discovering a few of my favorite things to do!

This year, I surprised my boyfriend with a full itinerary for his birthday and decided to keep him guessing by keeping it all a secret until I picked him up. He thought we were either going camping, driving up to Summer Fest or going to see a Seal concert in Europe {the last one was definitely wishful thinking for a weekend, haha}, but instead I decided that a night/day trip in downtown Chicago would be the perfect way to celebrate his early birthday. And since he’s still a newbie to the city, I packed in tons of cheesy tourist sightseeing opportunities, because you have to do it all at least once, right 😉

Here’s a play by play of my perfect weekend in the city! Most of these things we did, but I also snuck in a few suggestions if you happen to have more than a whirlwind 24 hours to staycation or visit Chicago.

Where to Stay

Freehand Chicago:

Finding the perfect play to stay in the city can always be a little challenging {especially during Chicago’s summer months!}. I first discovered Freehand Chicago last fall when I was shooting a visiting bloggers photos, and the moment I walked through the door, I knew I wanted to come back and stay there one day. Luckily for me, they had a room available for my little staycation getaway a few weeks back!

For those of you who haven’t discovered Freehand, it’s a hotel and hostel that has the cutest private and shared rooms in downtown Chicago. I love the bohemian chic decor, and the moment you walk through the front doors, you feel like you’re back in a cozy European hotel. 

Where to Eat/Drink: 

If you really don’t want to leave your hotel {I mean you should, but I’m not here to judge!} there’s a delicious coffee shop called Café Integral as well as one of the best cocktail bars in Chicago, The Broken Shaker {seriously, it was recently named the best new bar in Chicago by Time Out Magazine!} in Freehand Chicago.

After hitting up a cocktail {or two…} at the Broken Shaker, we headed to Bohemian House for dinner, which is one of my favorite restaurants in downtown Chicago. Besides the incredible ambiance and decor, it has the most incredible bohemian food, with dishes influenced by flavors from the Czech Republic, Germany and Austria. I always order the Chicken Paprika because I can’t get enough of it, but I’m also a huge fan of the schnitzel, beet salad and pretty much every cocktail I’ve ever tried there – they’re strong and super delicious.

We then made our way to Three Dots and A Dash, a famous tiki cocktail bar {and one of the first in Chicago}. The moment you walk in you feel like you’re in a 1960’s movie {think: Elvis in “Blue Hawaii”} with tropical wall paper, waitresses dressed in vintage Hawaiian prints and  a legit tiki bar. You have to make your way in through an alley {and maybe wait a few minutes to get in}, but it’s definitely worth checking out if you haven’t discovered it already. Their drinks are strong and tiki inspired, with drink names like The Dead Reckoning, Three Dots and A Dash and The Painkiller – and after one or two you’ll be feeling pretty good 😉

Before calling it a night, we ventured back to the hotel and hopped next door to the Berkshire Room, another favorite cocktail lounge downtown. Located in the ACME hotel, this bar has a very cool speakeasy vibe, and the cocktails are crazy delicious. Plus if you’re looking for a little midnight snack, they have a really tasty bar snack menu to keep you going the rest of the night.

For brunch the morning after {you might need it after your serious cocktail crawl…} I’ve always been a big fan of Cindy’s, located in the Chicago Athletic Association across from Millennium Park. Even if you just decide to do a hair of the dog cocktail morning, it’s pretty incredible – and the views of downtown Chicago never disappoint. I’m a big fan of the French toast and biscuits to start {clearly, my diet starts tomorrow….oops!} 

For lunch of dinner, I love swinging by Eataly to try out one of their many  restaurants {and usually end up eating a pizza or a cheese and meat plate that’s seriously out of this world….mmmmm!}. If you haven’t been, it’s basically a giant grocery store that also happens to have bars, restaurants and a Nutella stand {among other delicious desserts!} and it’s pretty magical. While I don’t get too many of my groceries there since it’s as pricey as you’d imagine, I love stopping in for a drink and a lunch/snack whenever I have some time to spend downtown. 

What To Do: 

Okay, I promise I do more than just eat and drink – but it is always the basis of a good trip in my book! Chicago is so beautiful in the summer that I always love walking around downtown, taking in the views of Millennium Park and the River Walk {below!}. 

Even though it’s a little touristy {okay, super touristy}, I love taking an architectural boat tour every few years, especially when introducing someone to the city. While it’s full of tourists, it’s actually pretty fun to spend 75 minutes on a sunny afternoon cruising the Chicago river and hearing about some of the most impressive buildings along the river. It’s pretty cool to hear all about the history of Chicago’s architecture and how the city was rebuilt from the great Chicago fire – plus the views aren’t to shabby too! I’d highly recommending bringing a camera or a phone to work on your Insta-game 😉 

After the boat tour, hope by the Willis tower Skydeck to see some of the highest {and most impressive} views of the city. We ended up skipping the tour this time due to the 2 hour wait {say whaaaaaat?}, but you can always buy tickets in advance to skip the line if you’re a little more organized than I am!

To discover a new area of downtown, I love hitting up the West Loop for some of the best restaurants and coffee shops in Chicago. Soho House is always a favorite spot, and I love getting a morning cup of coffee at The Allis {seriously, their coffee is delicious and makes you feel like you can conquer the world!}. It’s a nice indoor space to take a break, or you can stop by outside on their patio – one of my favorite places to relax in the summertime.

And to end the weekend on a sweet note, I love stopping by Cone ice cream, and Irish themed ice cream shop in the West Loop {seriously, it sounds bizarre but it’s actually really delicious!}. It’s the cutest spot to enjoy a scoop of ice cream {from normal flavors to Guinness/Irish mint!}, and anything that’s dipped in chocolate and sprinkles is good in my book.

Phew – that’s a lot of things to do in a weekend, but you’ve gotta pack it all in to make for a fun-filled weekend! And since I know most of you have {hopefully} made it to Chicago, you’ll have to let me know the fun things I missed on my list too! With only 24 hours, it’s hard to pack it all in, but we managed to hit up a few of my favorite places before totally burning ourselves out 😉 xx