A couple weeks ago, my roomie came to visit & I got to play chi-town tour guide for a few days. We had SO much fun exploring & I loved showing her my hometown! Like I said in my Instagram post, it was like the ultimate Bachelorette hometown date, roomie edition. A couple of the days, two of my other best friends got to tag along on the adventures, which added even more to the fun! 🙂
Because I’ve lived in the suburbs of this city my whole life, I’ve taken lots of fun trips downtown & gotten to see most of the tourist attractions. But I’ve also gotten to explore some of the lesser-known areas of the city & have found some of my favorite lil’ spots. So when planning an itinerary of what we would do for the days that she came to visit, I knew we had to do the perfect combo of the two; the perfect balance of getting in the major tourist attractions & seeing the lesser known beauty the city has to offer.
Without further a due, here’s my guide to a weekend in Chicago with your girls! (Or your fam, boyfriend- even yourself! And major props to you, girl. I’m all for solo travel.)
Day 1:
My roomie arrived at O’Hare airport at about 7 PM, so I knew I had to get her some yummy authentic Chicago cuisine to cure the post-flight hunger. Enter: Portillo’s. A true classic. Elena got a hot dog, I got a chopped salad (WHICH I HIGHLY RECOMMEND IT IS MY FAVORITE THING EVER), & we split some fries & their famous chocolate cake. Portillo’s is a must for a visit to Chi, and they are located all over the city & suburbs!
After dinner, we headed downtown for a drive down Lake Shore Dr, one of the most beautiful drives I’ve ever taken. My friends & I would sometimes hop on I-90, take the exit to LSD, blast some music, and sing our hearts out as we drove through the city with Lake Michigan to our left & the bright lights to our right. If you have a rental car, this is such a fun way to spend the night with your girls! Get your car jams playlist ready to go & hit the road, I promise it won’t disappoint.
Day 2:
We slept in a bit, then my sisters & I brought Elena to my old high school to show her around. Cause what is a proper hometown date without a high school visit, am I right?!
That afternoon, we all headed to Lincoln Park, one of my all-time favorite neighborhoods of the city, complete with cute coffee shops & boutiques & brown stone homes that I so wish I could afford right now, but #collegebudget.
Our first stop: Molly’s Cupcakes. Cause y’all know our family always does dessert before dinner in LP, & Molly’s is usually the culprit. I got the Samoa cupcake & Elena got something chocolate-peanut butter filled that was basically heaven in cupcake form. Molly’s is adorable & has such good vibes, perfect for an afternoon stop.
Next up: a walk through the Lincoln Park zoo lights. Us natives know that the sun sets at approximately 4 PM during the winter here, which is perfect for an early evening walk through the zoo lights! This is one of my absolute favorite things to do in Lincoln Park around the holidays. Grab your thick winter coat, some gloves, a cup of hot cocoa (which they sell!), and take a walk through the lights, see some cool animals, and even watch an ice sculpture carving. We got to see a penguin being carved and it was SO awesome.
That night, we knew we had to bring Elena to get some deep dish pizza. If you’ve never had deep dish, it’s a must during a visit to Chicago. My family’s absolute fave is a more local place by my house called Georgio’s, and if you’re going to be out in the suburbs, you 100% have to try it. But if you’re staying in the city, I personally believe Lou Malnati’s is the best. Cue the deep dish heart eyes.
Day 3:
After a morning getting filled-up with some wisdom in church, we headed to our day 3 destination: Wicker Park. And this time, another of my besties, Ellie, got to join the fun!
A lot of you know how much I love Wicker Park. Just take a quick peek at my Instagram stories from June-July 2018 & you will see the frequency with which I visited this ADORABLE lil’ part of town. It’s up & coming, has the cutest shops, lots of personality, and is super trendy.
The nice thing about Wicker Park is that, depending of course on time of day, you can usually find a parking spot on the street. We were able to find a spot super close to everything! (Elena & Ellie, if you’re reading this, I’m sorry again for my initial parallel parking debacle. You know, that one where I pulled into the spot with the tail of my car hanging out in the street at nearly an 180 degree angle. But hey, it’s the effort that counts, right! Lesson here: if you’re renting a car & don’t know how to parallel park, maybe take an Uber. 😉 )
After parking, we got brunch at The Bongo Room, which is a super yummy place that has a great atmosphere. I’ve been quite a few times now & love it every time. I usually get an omelette or some sort of eggs, but I’ve had friends get everything from pancakes to eggs benedict & they love it all!
After brunch, we walked around a bit and eventually stopped in Free People, which is a dangerous move for me because I want to buy everything in the store. BUT, y’all would be proud. I only made three purchases, and one of them was a gift, so that doesn’t really count. 😉 Ellie & Elena also got some super cute finds!
Next up: Volumes Bookcafe. This place is one of my absolute favorite places. EVER. Step inside & you will find a coffee shop, great music, & the cutest little bookstore. It’s the perfect spot to get some coffee, pick up a good book, and chill for a bit.
Day 4:
For Elena’s final day, I knew we had to go downtown & do all the big tourist attractions. That morning, we hopped on the Metra train to Ogilvie Station & met another of our besties in the city! I was so excited for our trio to take on the downtown adventures together. <3
We Ubered from the train station to the Grand Lux Café, which is a super yummy & pretty restaurant located right along Michigan Ave, a street that runs right through the heart of the downtown area & has all the best shopping. It has lots of windows overlooking Michigan Ave & it’s always fun to look out and see the busyness of the city below.
After lunch, we headed to Millennium Park to walk around, soak in the city skyscrape, & see The Bean, of course! After a lil’ photo session, we headed down to the McCormick Tribune Ice Rink, located right below. Entrance is free (woot woot!) & all you have to pay for is the skate rental. So if you have your own skates, definitely bring them!
I absolutely love ice skating & it was such a fun way to spend the afternoon with two of my sweet friends. Did any of you watch Ice Princess when you were little? One of my all time favorites. I’m convinced I’m the jumping shrimp sometimes. And if you don’t know who the jumping shrimp is, you need to watch the movie. ASAP. 😉
We had a blast & if you’re planning a trip to Chi during the winter, I highly recommend a stop here! After skating, we walked over to Starbucks across the street to warm up with some hot chocolate.
Next up was a visit to Navy Pier & a ride on the famous Ferris wheel. If you’ve never been, this is a must! The Ferris wheel has heated (yes, HEATED!) cars & takes you around for a view of the whole city. It’s so beautiful.
And finally, to end the day, we headed over the Gold Coast neighborhood for dinner at Three Arts Club café. This is one of the most amazing places I’ve ever been to, complete with chandeliers and the most stunning decor & greenery & an awesome ambiance.
———
And that’s a wrap on my guide to a weekend in Chi with your girls! I loved being able to play tour guide for a weekend with my besties in one of my favorite places, my home city. If you have any other chi-town faves, I’d love to hear about them in the comments! 🙂
xoxo
Always,
Elle