A Guide to My Favorite City: Chicago

Image via Urban Matter

It’s officially been four years that I’ve lived in the gorgeous city of Chicago! You guys seemed to love my Lincoln Park guide so I wanted to expand a bit and discuss my favorite spots in the city of Chicago as a whole, especially downtown.

Even though it’s been four years, I don’t feel like I’ve explored this city nearly enough. I realized that especially after putting this post together. I think it’s easy to get stuck in the routine of going back to your favorite spots over and over again. But, if you live in Chicago, let this serve as your reminder to go outside your comfort zone to try new things and places! Keep reading below to see my picks 😊


Mahalo // Though I’ve been to Mahalo for drinks before, it wasn’t until this summer that it really popped up on my radar as a hot spot to try in the city (especially for food). Just last month, Lexi and I were lucky enough to stop by and try out some of their dishes like chicken potstickers, poke, and more. I highly recommend this spot if you’re into Hawaiian fusion food and delicious drinks! There’s plenty of Insta opps here too 😊 The interior is stunning.

Rockit Bar & Grill // This place is a serious favorite of mine and Austin’s! Whenever we’re craving a burger, there’s nothing better than going to Rockit in River North. I’m a big fan of the Rockit and Black Angus burgers there. Don’t forget the truffle fries either. TO DIE FOR. If you’re into buffalo anything, the buffalo fries are killer too. For a burger joint, the nachos are surprisingly delicious as well! Truly, you can’t go wrong with anything here.

Benny’s Chophouse // If Aust and I have something to celebrate, you can pretty much count on us going to Benny’s. From anniversaries to New Year’s Eves to birthdays and graduation, we’ve been here countless times and always enjoy it (especially the service). I will say it’s not cheap but if you have the money to spend or something worth celebrating, it’s fantastic. Their steaks are probably my favorite in the city. We love the onion rings, mac and cheese, risotto, and calamari too. Is there anything Benny’s can’t do? Probably not.

Bub City // While I’m not from the South, I did live there for two years and my parents are still in NC so needless to say, I love some good BBQ. It wasn’t until I went to Bub City that I realized the delicious BBQ I’ve been missing in the city! Their pulled pork sandwich is a favorite of mine (with coleslaw, trust me on this even if you typically hate coleslaw). The baked beans, Nashville hot chicken tenders, and pomegranate margarita can’t be missed either. Love country music? Great. Bub City is an incredible spot for drinks and dancing too!

Image via Original Grain


Go to a Cubs game // Or a Sox game, but I personally prefer the Cubs! Wrigleyville is a neighborhood like no other that everyone living in or visiting Chicago should experience. Everyone bleeds Cubbie blue, especially on game days. It seems like the city comes to life when the Cubs play! Tickets can be expensive but you can get a great seat for a good price if you buy them ahead of time. Don’t forget to get a beer and a hot dog while you’re there either.

Museum hop // Chicago has a ton of amazing museums from the Art Institute of Chicago to the Field Museum and Shedd Aquarium. If you hit them all in one day, I’d genuinely be impressed! There’s so much to explore in each of them so I’d recommend picking 2-3 that align with your personal interests and visit those. I really love the Shedd because I adore animals but if I’m in more of an artsy mood, the Art Institute is fun (and a really great history lesson). For a list of Chicago’s top museums, head here.

Go on an architecture boat tour // I haven’t done this yet, but it’s on my list! A bunch of my friends and parents have gone and have told me it’s a great time and very educational in the sense you learn a ton about the city’s start and general history. Chicago’s architecture is one of my favorite things about it. There’s a handful of companies that do this kind of tour, but Chicago’s First Lady Cruises is the one that comes to my mind. Some offer brunch aboard too. Sounds like a great Sunday activity to me!

Image via Jenel Management Corp.


Southport Corridor // In Lakeview off the Southport Brown Line stop, you’ll find a ton of cute shops. There’s a great mix of more corporate stores like J.Crew, Free People, and Kendra Scott and true boutiques like Krista K, Click Shoes, and Two Penny Blue. Whatever your shopping style, you’ll find something along Southport. There are great restaurants here too (Tuco and Blondie for one) to fuel up after you’ve shopped your heart out!

Bucktown // I don’t make it over here often but early on in college, I used to work at Green Goddess Boutique and we had a location in this neighborhood on Damen Avenue. Stores like Nike, TOMS, LUSH, and more have shops here. Like Southport, there are great boutiques as well. JAX & DEBB is one of my favorites for men and women’s clothing. If you like shopping for vintage clothing, there are a plethora of vintage stores and resale shops here. More recently, a great clean/green beauty store opened called Credo Beauty.

Gold Coast // Similar to Michigan Avenue (and close by), you’ll find your favorite luxury brands here. I like to pop by Rebecca Minkoff, Kate Spade, and Tory Burch when I’m here to browse. Other less expensive spots worth stopping by are Madewell (J.Crew’s sister store) and lululemon. You can shop places like Hermes, Vera Wang, Marc Jacobs, and YSL if you really like luxury goods. Like I said, I prefer to browse but it can be fun to pretend or dream! Head a few blocks east for more affordable name brands on Michigan Avenue.

If you live in Chicago or have visited, where are your favorite spots? Let me know in the comments below and have an amazing weekend, everyone!

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