Last Saturday, I embarked on an adventure with my mom to none other than the lovely city of Chicago!

This was my first time in the Windy City, and I am pretty sure it will not be my last. I absolutely LOVED Chicago, and felt right at home amidst its gorgeous skyscrapers and lake views.

As soon as I left on my trip, I knew I would want to write a travel guide type post for you all because one of my favorite things to do is to plan itineraries and then share them with others. I spent hours researching the best places to eat, the must-try coffee spots, and the must-do activities. Some of the things on my list were only okay, which is totally fine! You live and you learn, and this way, you can rest assured that this post is filled with only the tried and true. The creme de la creme. The cream of the crop, and the flower of the flock. I’m done, I promise. 😉

We spent four full days in Chicago, which felt like the perfect amount to us. In a pinch, you could definitely get away with just three, but we loved the slower pace of the last couple days and getting to just leisurely explore the city on our own time.

There’s nothing better than strolling along, holding a delicious coffee, and exploring a totally new place with zero items on the to-do list and not a care in the world.

So if you’re ready, let’s dive into your one stop shop for all things Chicago!

What To Do

Chicago has no shortage of fun activities. Some are well-known tourist traps, and others are more off the beaten path. I felt like our trip was a good mix of the two, so here are some things I really loved doing.

Architecture River Cruise

I was very on the fence about doing this. My mom kept saying all her friends said it was a MUST, but I’m not too much of an architecture nerd. I thought it would be one of those “this is an art deco building, a style that was created in blah di blah…” (no shade if you love architecture LOL, but it’s not usually my thing.) However, I do love boats, so I begrudgingly agreed, and what do you know, it ended up being one of my favorite activities in Chicago.

We did the tour with Shoreline, and it was so incredibly interesting. I had no idea that Chicago is basically a city of architecture, as it was rebuilt by all the most esteemed architects after the fire in the late 1800s. The tour definitely made me appreciate the deliberate thought and effort behind each and every building that grazes the city’s skyline, and I was honestly spellbound for the entire 75 minutes.

The Field Museum

From the biggest complete skeleton of a T-Rex named Sue to one of the oldest hominids found so far named Lucy, the Field Museum is chock-full of super-cool things. I’m something of a nerd for natural history; it was always my favorite museum to go to in NYC, and this one was even bigger, cooler, and more awesome than the one in New York…Which I didn’t think was even possible.

Seriously, I spent like 4 hours walking awe-struck through almost every nook and cranny of the museum. I spent like an hour in the bird section, marveling at how many bird species there are. I stared at every African animal on display. I think what I love most about museums like this is they show you things you most likely would never otherwise see, things like animals from the deep wild, or animals that have long been extinct, or even mummies. I honestly could have spent 3 more hours there. Go!

Art Institute of Chicago

One of the most esteemed art museums in the world. I was super excited to see the Nighthawks painting and The American Gothic (unfortunately, the serious lady and gentleman holding a pitchfork were on tour in NYC precisely when I was in this museum…bummer LOL). I also loved the room of Monet. Impressionism is one of my favorite styles, and if you’re a fellow Monet fan, you’ll definitely be impressed by this museum’s collection.

If low on time, I would advise to just visit the highlights listed on the visitor’s guide because the museum is MASSIVE, and not every piece of art is a must-see, in my humble opinion.

Millenium Park

We walked through this park quite a lot, since our hotel was very close, and it’s also where you’ll find the Art Institute and Field Museum. It is also home to the famous Bean, or the Cloud Gate if we’re being technical. It’s basically a giant mirrored bean-shaped thingamajig that apparently you must get a selfie in front of. One of those super-quick stops that doesn’t hurt. 🙂

Chicago River Walk

We were lucky enough to be staying in a hotel right on the river, so this river walk was often our main way of walking through the city. It’s really nice to walk right next to the pretty river, and the path leads all the way to the gorgeous…

Lake Michigan

Words cannot describe how lovely this lake is. I could have sat in front of it for hours, just marveling at the sheer mass and beauty of it. We walked along it quite a lot on our trip, and it never ever got old. There are some boat tours on the lake, but we didn’t end up taking those, choosing instead to admire it from land.

Willis Tower

The renamed Sears Tower! This is the tallest building in the Western Hemisphere, which totally surprised me. Now normally I find observation decks to be pretty cool but huge tourist traps and not THAT worth the money. BUT. Please trust me when I say, you want to go to the Willis Tower Skydeck. It’s actually pretty affordable compared to some other cities’ observation decks, and it provides an unparalleled view of the city as well as far beyond all the way to Indiana, Wisconsin, Michigan, and the farthest parts of Illinois.

Pro tip: Go here around an hour before sunset (for us it was 7pm), and try to go on a weekday. The crowds weren’t bad at all, and the city was still steeped in daylight. As we enjoyed the view from every angle, the city slowly started transitioning to night right in front of our eyes. We got a gorgeous view of the sunset and then watched as all the lights turned on in twinkly clusters, giving us a best-of-both worlds experience of Chicago.

Comedy Show at The Second City

I’d heard many good things about this place. It was the stomping ground of such greats like Tina Fey, Stephen Colbert, and … so I knew I had to include it in our nighttime plans at some point. We ended up going to the improv hour, and you guys, it was the BEST comedy show I have ever seen. Ever. I was laughing the entire time. To be honest, I was in a bit of a crummy mood before the show, as I was tired and just out of sorts, but all of that went out the window as soon as the show started. Trust me, this is a must!

Wicker Park/Ukranian Village

Not an absolute must, but this was one of my favorite parts of Chicago to explore. We went here on our last day, so we were pretty free and relaxed, having already seen all the main sights. Wicker Park is this trendy part of Chicago that’s home to some of the best coffee shops and brunch spots of the city, and along with the Ukranian Village, shows a totally different side to the city than Downtown. This part is much quieter and more quaint, without feeling suburban at all. It still feels like Chicago, but a Chicago of a slightly different dimension.

Where to Eat

This is a pretty brunch-heavy list, as we often ended up just grabbing dinner where it was convenient, and Chicago does love its brunch, so I focused the itinerary on that. I will also include a couple places I didn’t get a chance to try, but have heard great things about!

Beatrix

We loved this place so much that we went here 3 times. No joke. It helped that it was a mere 10 minute walk from our hotel, located in River North. Favorites from the menu were the Cauliflower Grits, the Quinoa Cakes with poached eggs, and the delicious Chia Cereal Bowl. I honestly could have gone there 5 more times because there were so many more things on the menu I wanted to try. Also! Two of the three times I got the Iced Banana Joe, which is an iced coffee blended with a banana. Do yourself a favor and GET IT. If you like bananas, this is DREAMY.

The Allis at The Soho House

Trendy, Instagrammable, and an absolutely delicious brunch. What’s not to love? I was a huge fan of the plush pastel couches, the general decor and vibe of the place, and the make your own omelet (ham, goat cheese, and mushrooms for moi).

Goddess and the Baker

I heard tons about this place and was super excited to see that it was a short walk from our hotel as well! I ended up getting the Special smoothie bowl, which was a matcha green smoothie bowl. It was good, but what I was really after was the dessert. The cheesecake brownie was OUT OF THIS WORLD. What, you don’t have dessert after brunch? 😉

Lou Malnati’s

Deep dish pizza is a must when in Chicago. You may be familiar with the long-time battle between the two main deep-dish restaurants, Lou Malnati’s and Giordano’s. After a LOT of research, I decided on Lou Malnati’s, and we were not disappointed. I loved that the crust there was thinner than I was expecting with deep-dish, which didn’t make it super heavy. We got the Chicago Classic one, which came with lean sausage, mozzarella, and tomato sauce.  We also split a strawberry spinach salad because #balance :p

Bandera

This was a pretty random choice because we were starving one night and the few places I had on my list were either super far or had already closed. LOL, really, 9pm??

Well we ended up loving this place so much that we came here twice. If you go, GET THE SKILLET CORNBREAD. This is not a drill. I swear it’s worth everything, and you better bet we had it two days in a row. Also delicious was the BBQ salmon, which we also split for the perfect meal.

Jeni’s Ice Cream

I believe I’ve raved about Jeni’s before, as it recently opened in DC, but seeing as they have a couple locations in Chicago, I knew I had to introduce my mom to the deliciousness. One of the days was in the high 80s, and ice cream was the perfect mid-day treat to fuel the abundance of walking we were doing.

I got a half scoop each of Brambleberry Crisp and Cookies ‘n’ Cream on a waffle cone, and I never wanted it to end. <3

 

Some spots I sadly didn’t get a chance to try, but know for a fact are amazing, are Baker Miller Bakery, Ann Sather, Lula Cafe, The Winchester, Summer House Santa Monica, Eden, Range, Little Goat Diner, and Do-Rite Donuts.

Where to Get Coffee

Is anyone shocked that this is a separate list? Chicago LOVES its coffee, and they do it WELL, so if nothing else, just trust me on these?

Dollop Coffee Co

This was the first coffee place we went to, on our very first day there, and it was lovely. Their staff is the absolute sweetest, and their locations are all perfect for spreading out and lounging with a good book. So I did just that with my Harry Potter book, while my mom caught up on the royal wedding on her phone. 🙂

Their coffee is reliably delicious too!

Intelligentsia

One of the most famous Chicago chains that I was super hype to try. They’re quite famous for their oat milk lattes, or at least that’s what the Chickpea in the City always raves about hehe, so of course I had to get that.

My mom and I both loved our hot oat lattes, and we enjoyed them with a bag of Garrett’s popcorn (which by the way was good but not great; a little greasy and heavy for our liking).

The Wormhole

Ah, words cannot describe how adorable this place is. It’s all 80’s themed with a DeLorean parked inside, tons of Star Wars relics, and a bunch of 80s movie posters all over. Plus a bunch of other things I couldn’t even identify ’cause, well, I’m a late-90’s kid.

Their coffee was so so good; I got the cold brew with almond milk, and savored every last drop as I sat looking around at the cool interior. A must!

Caffe Streets

Okay. This was easily the best coffee drink of the trip. Honestly one of the best coffee drinks of my life, on par with Portland’s Heart vanilla latte.

The drink I am talking about is…the iced banana oat latte. Okay, please bear with me. I know this is the SECOND time I’m mentioning bananas in coffee and you’re probably thinking bananas have no place in coffee, and this gal is CAH-RAZY, but I promise you this drink is mind-numbingly delicious.

They use real banana in the latte, and the oat milk works perfectly in there to create a party in your mouth. It’s like a coffee banana milkshake. But better. Ugh, I can’t. I wish I could order it in mass quantities to my house, but I’ll just have to settle with getting each and every one of you on board with this if you ever visit. Seriously, guys, it’s that good.

 

And a couple I sadly didn’t get a chance to try are CC Ferns and Asado. Both have the CUTEST interiors and supposedly amazing coffee, so make sure to hop in here if you get a chance. They both do close quite early, and Asado doesn’t always follow the hours on their website, so I would advise calling ahead.

A couple more tips for you:

1. Get the Chicago GO card to save big on major attractions; you can even build your own and put only the attractions you know you’ll visit. You also get to save time in lines this way!
2. Walk everywhere! Walking is the absolute best way to get to know a city. Well, that and going on a quest to try all the best coffee and food hehe. But I seriously walked over 20k steps most days there and didn’t even think about working out. Trust me, walking that much is a HEFTY workout in and of itself, as was apparent by both my mom’s and my appetites at dinner. 🙂
3. Indulge more than you normally would, but don’t throw all healthy habits out the window. I still made sure to have a few servings of greens or fresh veggies in my day, as well as some fruit. I tried to make sure most of my meals were balanced and contained enough of each macronutrient to keep me fueled. I also stuck to journaling every night, partly because I wanted to record all the memories, and partly because it’s necessary for my sanity. That being said, allow yourself to let loose a bit. That’s what vacation is for, isn’t it?

I hope you all enjoyed my Healthy Chicago Travel Guide. Travel is one of my absolute favorite things to do, and I hope to have lots more guides like this one on the blog in the future. Please feel free to comment your favorite Chicago activities and places, and hopefully this post has awakened some wanderlust within you. 😀

Linking up with Amanda today!

 

Ever been to Chicago?

Do you enjoy traveling? Do you tend to stick to routines when traveling or do you treat yourself a little more?