What To Do During a Weekend In Chicago

Reckless Records in Wicker Park

This is by far my MOST asked question, and I seriously liiiiive for it!!! I post pictures of Chicago scenes to my Instagram all the time, am a huge foodie and spend my weekends eating my way around Chicago (and even have an entire Insta Story highlight featuring my food adventures!), and I just absolutely love living here and think it’s one of the best cities eva— I love giving out recs and thought it would be of extra help to some to share exactly what my itinerary would be if I only had a few days in town!

Definitely worth noting that Chicago is a totally different scene depending on what time of year you visit; both would be a super fun time, it just depends on what you’re in the mood for. For this post, I’m going to highlight what I would do if I was in town this time of year.

One thing that I loooove about Chicago, is that unlike a city like New York or LA, the majority of the neighborhoods I normally hang out in are all relatively close together, you’re talking like a 10-12 min Uber ride or a quick L ride (Chicago’s above ground subway system). I can brunch in West Loop, grab coffee & donuts in River North, walk around Lincoln Park, and eat dinner in Old Town. And yes, that is a day that I’ve done before lol.

Let’s start with Friday night drinks. After arriving at your hotel (I love The Langham, and have also heard great things about The Conrad), head to West Town to hit up the always delightful, equal parts quirky, exotic, and oh so trendy Beatnik; there are massive plants everywhere, hanging chandeliers, Moroccan rugs, brightly colored tile floors, fun music, and the most amazing cocktails and bar bites. They have killer drinks and the ambiance is just so cool. I also love Beatnik for dinner and brunch. With so many other amazing food choices in Chicago, however, I would probably put Beatnik on the list as a fun place to grab a pre dinner drink. The bartenders really know their stuff, the drink menu is inventive and different, and there are tons of delicious options for a light bite to eat.

Brunch at Beatnik

Call an uber and head into River North for Sushi-San; it’s relatively new (sister restaurant to another one of my faves Ramen-San), and has unreal sushi and other small plates. One of my favorite dishes is the Tako Taco, which is a fun take on a taco, with a crispy seaweed shell and spicy octopus and aioli; oh my god it is so freaking good. The Roasted King Crab sizzling rice is also heavenly… It’s really hard to go wrong here. The drinks are spectacular; their old fashioned comes with a huge square ice cube with a picture of a famous 90’s rapper inside. It’s amazing. I love the La Croix-Ing Tiger; they cut off the top of a La Croix can and add sake and other light, yummy stuff… topped with a pink umbrella lol. It’s really refreshing! The Cilantro Lime Marg is also awesome. If you’re in the mood for sake bombs, ask for the citrus-y one! Absolutely delicious and a fun way to get rowdy!! Overall it’s a really fun scene and River North is crazy poppin’ Thurs-Sat nights, so you’ll feel really in the action and will be smack dab in the middle of tons of bars if you wanted to go out after.

I also highly, highly recommend checking out the local Chicago theatre scene for a show (I recently saw Aladdin and The Lion King on Chicago broadway) or hit a comedy club for some late night stand up. I loveee going to Second City- they always have a couple different seating times, in addition to their standard improv shows will often have a scripted “themed” show. I saw their holiday special back in December and it was hilarious. It’s historic to Chi town and made some of the greats (Tina Fey got her start here!).

For Saturday brunch, there are sooooo many amazing options… I love love love brunch! I would have to go to the Allis, at Soho House Chicago in West Loop. There are the best food options, and the interior is just so dreamy. I’ve posted this place on my Insta a million times! Fran and I eat here all the time and always stay for the longest time just enjoying the vibes haha. One of my fave avocado toasts in the city, and I also love the Allis breakfast; you get eggs of your choice, roasted tomatoes, smoked salmon, sliced avocado, and bread of your choice. Everything is fantastic and I love that you get a little of everything! Also love their shakshuka and their banana bread! It’s located in the West Loop area, which is one of my favorite places in the city. If you have room/time, get a military latte at Sawada across the street, it’s this super cool and hipster coffee shop. The military latte is a matcha latte with a swirl of expresso; I was super skeptical at first, but it is out of this world good. The expresso has major chocolate tones, is bittersweet, and pairs perfectly with the matcha. A fun take on a classic!

The Allis “Breakfast”

Military Latte at Sawada Coffee

Okay, now you finally have the entire day ahead of you. As far as staple “touristy” things go, if this weather is decent I would definitely check out the Bean (official name is the Clout Gate), in Millennium park. It’s this super famous sculpture that is reflective like a mirror and looks like a giant silver bean! The 360 Sky deck walk at the Hancock is also a worthy tourist activity- you get to see some amazing views of the city and walk out into this glass box that suspends you out of the actual building! Not for the faint of heart hahah. The Lincoln Park Conservatory is gorgeous and a great place to take a walk around and enjoy all those botanicals! Super picturesque and it just feels lush- something a little different.

If you’re coming during the warm months, the architectural boat tour on the Chicago river is a must (I’ve done a million times and I always learn something new about the city). The tour guides are always awesome, really funny, and it’s just a great way to enjoy a nice day and see the whole city. Cindy’s Rooftop also has amazing city views and is the perfect place to grab a drink and live large!

Punch Bowl Social just opened up in West Loop and is this massive space filled with a bowling alley, bocce, karaoke, multiple bars, and is just super quirky and cool!

I’m a huuuuuge small plates restaurant fan, so for a Saturday night dinner, my go to’s would have to be Ada Street (they have a little bit of everything on the menu) or Ema (more Mediterranean style)- both have very skilled and knowledgeable bartenders and killer drink menus. I love the ambiance at both these spots- very lively and hip. Ada Street is right next to this cool hot pink painted garage wall and has a courtyard with ping pong tables and twinkle lights in the summertime.

The avocado pea dip and warm pita at Ema… heavenlyBrunch spread at The Little Beet Table

Sunday I would highly recommend The Little Beet Table for brunch. Everything is seasonal, fresh, light and healthy, but UNREAL good. I was just there recently with my parents and I swear we ordered the entire menu- they have this delicious cauliflower hummus you can get with grilled pita and a huge board of raw vegetables for dipping; their banana bread is warm and comes with this pecan butter spread on the side and it no joke is one of the most heavenly things I’ve ever had. If you’re into olives, you can order a little bowl of them; they’re seasoned with a citrus salt and oh damnnnn they are good. The sweet potato toast with fresh sunny side up farm eggs is simple but always so satisfying!

I would then head out for some shopping, because what trip is complete without shopping?! The restaurant is right in Gold Coast, which puts you right downtown and by a ton of stores. My favorite place to shop is the E Oak Street area; if you put Barney’s New York into your google maps it’ll put you exactly where you want to be. It’s so cute and charming here!! They have a Madewell and Aritzia and some other more budget friendly options, as well as super high end designer stores- always fun to window shop (or treat yoself)! You’re also right around the corner from Michigan Ave, which is definitely worth checking out! Always busy, but it’s a gorgeous, famous Chicago Street with every store you could ever imagine.

Other fun areas to explore include Wicker Park and Lincoln Park. Wicker is super funky; tons of wall murals everywhere, little coffee shops, hip boutiques… The Wormhole Coffee shop is such a cool scene, I love their almond croissants and lavender and activated charcoal lattes (sounds strange but works so well!)

Lincoln Park is so picturesque and charming; I love just walking around the neighborhood on a nice day and admiring all the beautiful walk up style condos! Be sure to check out my fave boutique Alice & Wonder if you’re in the area!

The most gorgeous Lincoln Park “walk up”
Wall mural in Wicker

Shopping on E Oak and Rush

If you have time to spare, end your trip at the 3 Arts Cafe at the Restoration Hardware store (I’ve posted a bunch of pictures of it on my gram before and it is like nothing I’ve ever seen before!). The restaurant/bar is in this giant atrium, filled with trees and chandeliers everywhere. Grab a glass of wine and order a charcuterie board and just reeeeelax. You won’t regret coming here! Be warned that if you come for brunch, there often is a long wait, maybe an hour/hour and a half. The food is just eh to me, which is why I would suggest coming for a glass of afternoon wine! Which is a thing. Afternoon wine is an activity guys. They also have excellent donuts for the record.

And just like that you’ve successfully completely my perfect weekend in Chicago!! If you guys ever have any questions or need recommendations of where to eat, stay, or do, you know where to find me! I love talking all things Chi-city 🙂

I also wanted to throw out a few other of my fave restaurants for brunch/dinner in case any of the above don’t work out!

The infamous Rose All Day sign at Hampton Social