A (Summertime) Chicago Guide for Newbies
POV: You’re planning a weekend getaway to Chicago. You’ve only got 48 hours to cram in the full Chi town experience, but you don’t know where to start.
Listen, I get it. Chicago is a huge city, and there are endless possibilities at your fingertips. I’ve lived here for almost 5 months now, and I feel like everything I’ve done is just the tip of the iceberg. With that said, I feel like I could confidently recommend a weekend’s worth of activities to someone who isn’t familiar with the city. Don’t worry, I won’t make you feel too touristy either - the Bean is great, but after looking at it for all of 5 minutes and snapping a few selfies, there just ain’t much more to it. By the end of this list, you’ll be feeling like a local. I hope you have good walking shoes.
Start off with a coffee from La Colombe and a bagel from Gotham Bagels. You’ve got a long day ahead of you, so you’re going to need to fuel up accordingly. There are two Gotham Bagel locations in Chicago, but if you go to the one on Dearborn you can head around the corner for a coffee at La Colombe on Elm St to go with it. Important to note: Gotham is still doing online ordering only, so plan accordingly!
Next, take a stroll down Michigan Ave. If you don’t mind some crowds, take a walk down Michigan Avenue. There are a ton of different stores you can pop into, including Zara, The Disney Store, and the Starbucks Reserve (not to flex, but it is the world’s biggest Starbs. Head to the top floor for an espresso martini). You’ll also find many of the designer store fronts along Michigan. If you take it far enough, you’ll hit…
The Chicago Riverwalk! There are several staircases that will allow you to dip down to river-level, and I highly suggest you find one. You can easily kill a couple of hours walking along the river and watching the boats pass you by. There are a ton of restaurants and cafes that line the path if you get hungry, or you can take a seat on one of the stretches of public benches. There’s something uniquely calming about sitting still on the riverfront while throngs of people pass you by. IMO, the riverside views are 10/10 here.
While we’re on the subject, you’ll want to check out the lake as well. There are beaches scattered up and down the lakefront, but there is also a concrete path that hugs the edge of the vast body of water that is Lake Michigan. I recommend starting in the Lincoln Park/Old Town area, and walking south towards the city (bonus points for a sunset stroll). You’ll get amazing views of the skyline, and I promise you will feel very zen. In case you were wondering, this is my favorite route for hot girl walks.
Support some local businesses by attending a farmers market. During the summer, your farmers market options are endless here. You could spend a whole day strolling through some of them and never go hungry. I really love the Green City Market in Lincoln Park (open Wednesday and Saturday), but here is a great rundown of all the markets that are available to you.
By now, you’re probably ready for some indoor activity. To get out of the heat, head to one of the many incredible museums that are on Chicago’s roster. Personally, my top choice is the Art Institute - the caliber and variety of art here is unmatched. Another honorable mention is the Museum of Contemporary Art, which offers pay-what-you-can admission. For those who are less inclined to look at art all day, the Field Museum or the Museum of Science and Industry are equally great options!
For din, pick from a plethora of options. I feel like I can’t fairly recommend one dinner option over all the rest because there are just. so. many. For a dinner on the classier side, I really like Gemini or The J Parker (insane rooftop views!). For a more casual meal, try Broken English Taco Pub (order the Cucumber Ranch Water and thank me later) or Parson’s Chicken and Fish. Both have multiple locations, so no matter where you are in the city one will probably be close by.
It’s time to hit the town. You’ll start your night out with drinks at Benchmark or 80 Proof. Amidst the hustle and bustle of Wells Street in Old Town, these neighboring bars are the perfect place to get a sit-down drink before fully letting your hair down for the night. Both have a great selection of cocktails and laid-back vibes until about 9pm, at which point the crowds start to roll in. If you’re looking to extend cocktails into a full night of drinking while staying in one spot, Benchmark is the better option IMO. Bear in mind that the lines for both spots will grow rapidly after 9:30ish, so if you’re going to make a move, do it before then. If, however, you’d rather bop around and get a little crazy for the rest of your night, you’ll want to head up the street and…
…End the night at Utopian Tailgate. I. Love. Utopian Tailgate. This rooftop bar has an indoor/outdoor space, and the vibes here are nothing short of immaculate. With a giant disco ball in the middle of the room, you have no choice but to bust some serious moves on the dance floor. If you stay long enough, keep an ear out by “Shots” by lyrical geniuses we know as LMFAO. At this time, the staff will make the rounds armed with Super Soakers filled with tequila, and let me tell you, no one is safe. Utopian Tailgate will almost surely be your final stop of the night, but it will also be your best one.
And that, my friends, is my summertime Chi beginners weekend guide. I’ve just barely scratched the surface of things to do here, but I can confidently say that these places will give you a top-notch weekend. This list will, of course, be amended and updated as I continue to explore and get to know my beautiful city. :)
xo, Ellie