36 Hours | Chicago Illinois

I’ve always loved Chicago. I actually planned on moving there after I graduated from college, but just never got it together enough to actually do it. So now it’s one of my favorite places to visit! I thought it would be a great place to base my next  36 hours series post on. Here’s my cheat-sheet to the latest everything and anything fun, yummy and fabulous in Chicago. I organized it in a way that makes it super easy to traverse and explore without having to double back or get lost. Enjoy!

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Last month I had an amazing opportunity to check out a new boutique hotel line by the Hyatt called Hyatt Centric. Hyatt Centric hotels are focused more on the modern traveler and are located in popular, urban locations. The decor leans towards modern and it will fulfill all of your hipster fantasies 😉 Also their concierge is knowledgeable in all of the latest, trendiest places. So places that your average tourist just doesn’t hear of. Does this sound amazing? Yes. Yes, it does. And it’s totally my kind of traveling. So when I got offered the chance to check out the new Hyatt Centric The Loop, it was an emphatic YES, please 🙂

NATIVE FOODS  |  HYATT CENTRIC THE LOOP  |

HYATT CENTRIC THE LOOP  |  AIRE

ART INSTITUTE  |  JENI’S ICE CREAM

DAY ONE

COFFEE + breakfast
do-rite donuts and coffee
I wanted to start my first morning in Chicago off right, and what’s better than donuts and coffee? I love hitting up locally-owned coffee shops and Do-Rite was even better because it had DONUTS. And just any donuts…they even had vegan donuts! I bought a vegan blueberry cornmeal pancake donut with maple buttercream. ZOMG so freakin’ good you guys. And yes, my soymilk Dark Matter latte was the perfect pairing 😉 $7

do
architectural walking tour
After a morning pick me up, it was time to walk around the town a bit and get to know it. I met up with Chicago Greeter, Maureen who walked us all over the downtown area sharing fun tidbits, gossip and facts about Chicago’s most well-known architectural landmarks. She was a fun little firecracker of a lady and so completely entertaining and enthusiastic about her adopted city. Her stories were a delight and her British accent made them even better. Definitely one the best ways to get to know a city I tell you. AND huge bonus, it’s FREE. Yes, that’s right, totally free. And amazing. So do it 😉

LUNCH
HOWELLS AND HOOD
Try to end your walk near the river and then it’s just short jaunt over to Chicago’s Tribune Tower (a historical landmark) and a gorgeous feat of architecture with its notorious flying buttresses. On the ground floor you’ll find a great place to stop for beer and lunch. And actually its the place to be if you’re a beer aficianado, because it’s has the most beer on tap in Chicago. Pretty impressive. I ordered the beet salad which was perfectly filling, but not to much to weigh me down. Places to go and people to see and all that…$25

play
CHICAGO BOAT TOUR
After lunch head back across the river and down to the riverwalk and hitch a ride on Chicago’s First Lady. I sat on the top deck and got a great view of the river front. I’d definitely recommend a warm jacket that cuts the wind. And a hat! Be prepared 🙂 It was great seeing all of Chicago’s famous architectural feats by boat. And it was a lot easier to get a good view of them rather than on foot. The tour guides on these tours are volunteers as well. It’s so great to see the enthusiasm, the locals have for their windy city. $40

STAY
HYATT CENTRIC THE LOOP
It was quite the day already, so I decided to check in and take a minute to recharge (and warm up) at the hotel. I walk into the lobby and impressed right away with the amazing artwork in the lobby. The paintings are by the super talented Francine Turk, and were custom made for the hotel.

The hotel itself is housed in a historic 1927 art-deco building right in the heart of the loop. One on the best places to be in Chicago because you’re pretty much dead-center to everything. The building used to be offices but has been converted quite successfully into modern chic hotel rooms. When renovating they kept most of the historical touches, for example the presidential suite is completely walled in original wood paneling and is jaw-dropping.

The rooms themselves are all different, but were created with a minimalist-style that I admire with an eye to efficiency and…luxury. The rooms are “smart” as in they know if you’re in the room or not and adjust the thermostat accordingly. The beds are super comfy and the linens are high quality. They even embroidered my initials into my pillowcase. What the…how awesome is that?!

There’s a lounge area on a lower floor that has tvs, games and free snack foods available at all times. I found myself down there quite often grabbing an apple or snack mix. They even host beer tasting and other fun events there. So fun. $180/nt

drink
airE
After unpacking and a bit of relax time, I realized it was perfect time for happy hour. I decided a trip to the Hyatt Centric’s roof-top bar, Aire, was in order. This place is the perfect after work happy hour destination. And actually seemed like a locals’ favorite. It was busy without being too crowded. I enjoyed some bubbly perched in front of a fire pit and got to watch the sun go down. Ahhh. $15

shop
humbolDt house
After spending most of my time downtown, I wanted to venture a little farther out of the box. Perfect opportunity to hop into an Uber and do some window shopping. I’d been jones to visit Humboldt House after seeing all of the eye candy on their Instagram account. Destination decided. And this place lived up to my expectations. Old and new mixed together with locally-made artisan items ranging from beauty products to home goods. A total feast for the eyes.

DINNER
parlor pizza bar
What’s a visit to Chicago without pizza, am I right? This is a fun new place that’s not your typical Chicago-style pizza, but just as tasty and reasonably priced. Their wood-fired pizzas offer local ingredients and is always super fresh. Their specialty pizzas are fun and sometimes a bit adventurous. Example? A guacamole pizza! Great scene at night too. $25

HOWELLS AND HOOD | GATHER

HYATT CENTRIC THE LOOP  |  CHICAGO BOAT TOUR

HYATT CENTRIC THE LOOP  |  COCHON VALANT

DAY TWO

BREAKFAST
COCHON VALANT
I’m always one for breakfast in bed. I decided this morning was the perfect opportunity. The Hyatt Centric offers room service a little bit differently with their knock-and-go style service. The restaurant in the lobby, Cochon Valant provides the food from the room service menu. With knock-and-go, basically you place your order and when it’s ready the bring it up to your room, they knock on your door, place it down and go. You’re free to open the door in your pjs snag your food and run back to bed 😉 I ordered the vegan muesli cereal and it came looking like a work of art with the way the fruit and cereal was arranged. Loved it! They have great coffee too, so if you feel like a coffee before a coffee, they have your back 😉 Cochon Valant offers a great lunch and dinner menu as well. $16

COFFEE
wormholE
Time to head out to explore some more. And one of my favorite neighborhoods is Wicker Park. An easy trip on the “L” and you’re in hipster central. I’d say it’s time for another latte. Wormhole is hipster coffee at its finest 😉  $4

BREAKFAST II
GLAZED AND INFUSED
After getting my caffeine fix squared away, it was time to window shop. Wicker Park is full of fun shops and restaurants. Walk down Milwaukee Ave and pass by the Glazed and Infused window. If they still have donuts (they tend to sell out super early) buy a few of those puppies and enjoy a mid-morning snack. Those extra calories are WORTH it! $3

SHOP
gather
Right past Glazed and Infused you’re going to want to turn left on North Ave. Keep walking until you see Gather. Then walk in and just enjoy. Another great shop like Humboldt House, you’re going to find unique home goodies and fun apothecary items. I spent a good half hour in this small shop and enjoyed every minute of it.

LUNCH
native FOODs
While walking around Wicker Park I stumbled onto Native Foods Cafe. It’s actually a vegan food chain, so not a locally-owned place, but tasty and reasonably priced vegan food nonetheless. I ordered the chicken, bacon, avocado club with lemon dill potato salad, a lemonade and a vegan carrot cupcake. Deliciousness! $18

do
ART INSTITUTE or Lincoln Park Zoo
Time for some adventure. I’d recommend either the Art Institute or the Zoo. The zoo is a little bit closer to Wicker Park if that helps. I decided to hit up the Art Institute this time around though, and it was beautiful and inspiring and pretty-much everything you’re imagining. Definitely a must-see. $29

DINNER
antique taco
Back to Wicker Park we go! I wanted to hit up this super, fun and trending taco spot. They have a tasty-looking taco selection, I tell you. I’d highly recommend the habanero popcorn too. Grab a margarita while you at it and enjoy. $25

DESSERT
jeni’s ice cream
Desert, oh, desert! Do yourself a favor and swing by Jeni’s. You won’t be sorry! Everyone loves ice cream! $5

DRINK
violet hour
Since you in the neighborhood, who not swing by this institution. One of Chicago’s most popular bars, this is a fun one folks. AND it’s not just fun, their drinks mean business. They have a James Beard Award-winning bar program and offer a seasonal cocktail list that changes with the season. $15


I hope you enjoyed this peek into the less touristy, more aesthetically-pleasing side of Chi-town 😉 Let me know if you’ve visited any of the spots I mentioned OR if there’s any cool spots I missed.  Would love to swing back around and visit them next time!

You can also view my google planning map here.