5 Places You Need to Check Out When You Visit Chicago

Guys. Have you ever been to Chicago? If you haven’t, you need to go, STAT. Up until a couple of weeks ago, I’d never been either. Luckily, I work closely with a few team members who are in our Chicago office and I was able to go out their for some facetime with a handful of our bigger clients – it’s STUNNING!

Don’t get me wrong, I love NYC – there’s really no other city in the world quite like it, and it’s my home. But Chicago is like a cleaner, smaller version of Manhattan – ya know, without the urine-scented sidewalks and trash built up 7 bags high. I took full advantage of my downtime to explore, and here are some of my new favorite spots!

Lakefront Trail

It may sound silly to say this if you haven’t been to Chicago before, but the Lakefront trail was easily my favorite place in the city. It’s this 18 mile long stretch of concrete trail that follows along Lake Michigan, and it’s GORGEOUS!! The view is really what makes it, as the water is a bright blue/green that looks so appealing, you’ll wanna jump right in… until you remember that the water is probably 40 degrees and then you pass. I went for a few jogs along the portion that runs parallel to downtown, and I couldn’t stop smiling. It was honestly creepy, and I prob freaked out the locals, but its fine.


Oak Street Beach

I discovered this absolute gem on my first morning in the city. It’s right along the Lakefront trail and when I saw it, my eyes nearly fell out of my head. Like, ok, I get it, Chicago is pretty or whatever, but this is seriously something I’ve never seen before. It’s a stone’s throw (literally) away from the office buildings in downtown Chicago. Like if you walked about 150 feet (across a majorly busy road) you would be stepping into an office building). The beach is pristine, with cushioned lounge chairs, volleyball nets, lifeguards and a restaurant/bar area. AND ITS PUBLIC. WTF?! In NYC, you’d be charged a $2,500/month membership fee for something like this. Bible, I almost moved just so I could go here every day.



Navy Pier

Yet another incredibly cool part of  this city. On my first morning, I have about 5 hours to kill until a business lunch, so I was able to take advantage of exploring. Apparently I was in Chicago at a great time, because it wasn’t cold at all, but it wasn’t crazy hot yet (which you should note, because their temps can get seriously toasty in the summer). I was staying in Old Town, so I walked about a mile and a half down to Navy Pier and fell in love! TBH, I wish my boyfriend had been with me because it would’ve been a super cute date, but I managed on my own. My must-do’s of Navy Pier? The Ferris wheel, the Crystal Gardens and the Rolling Stones exhibit (which is open until 7/31!). The Ferris wheel was slightly pricey – $15 for an adult ticket – but worth it, in my opinion.



Crown Fountain in Millennium Park

Millennium Park is somewhere you should visit as a whole, of course, but on a hot summer day, you can’t pass up Crown Fountain! I was feeling a bit ~steamy~ from walking around all day in a black shirt, and felt like a little kid as soon as I saw this fountain! It’s definitely a little quirky- there are 1,000 Chicagoans faces that loop on the massive video screens in the fountain. But the feeling of splashing around like a 7 year old on summer vacation is something that gave me the happy feels.

mill park


The Architecture Tour

TBH, I’m not as obsessed with this as I am with everything else on my list, but it’s a must-do in Chicago. Tickets are not cheap- in fact, they’re $45 a pop. And at some points it can feel a little monotonous. HOWEVER- the scenes are so drop-dead gorgeous that its worth it. This is a boat tour that coasts along Chicago’s famed riverwalk and points out the world renowned architecture that lines the city. The riverwalk is the prettiest body of water I’ve ever had the experience of hanging out in, which is the biggest reason I’d recommend it- the wildly structured skyscrapers are a close second. If you have some extra time, check it out!


Have any really cool suggestions of Chicago must-sees for my next work trip? Comment below! xo, AJ


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