Kaylie & Dion
Things To Do
Urban Kayaks on the Chicago River
An amazing way to see the sights downtown and get your workout on! We've done both a guided architecture tour on the river, and a self-guided session on the lake exploring the marina, and both were amazing.
High Five Ramen
Okay I know it's the summer but if you're in the mood for ramen, High Five might be our favorite Chi restaurant. It's a tiny gem in the basement underneath Green Street Meats, and you can find the entrance in the alley, just look for the door with the handprint! Be prepared to wait, it only has about 15 seats inside, but wandering West Loop in the meantime is always fun!
Cloud Gate
"The Bean" is possibly the most basic tourist destination in Chicago, but it really is worth seeing! Also the location of our very first picture together as a couple on social media :)
Chicago Architecture Center
If you're into architecture, the Chicago Architecture Foundation River Cruise is amazing! P.S. there's a bar on the boat :)
Offshore Rooftop & Bar
The biggest rooftop bar in the country! The views of the city and lake from the Navy Pier are incredible!
WNDR Museum
Get your Basic Instagram Bitch on at this cool interactive art museum! Recommend getting tickets a good deal ahead of time.
Oak Street Beach
Yeah it's a beach in the the midwest, but the city views and a cool beach bar make up for that! If you're feeling active, we love renting Divvy bikes and riding south on the Lakeview trail to the Navy Pier or even further to the Adler Planetarium, all the views are amazing. Download the Divvy app to find bike stations!
Cabra
Peruvian food holds a special place in my heart, and I've turned Dion onto it now too. But it was easy because Cabra does it right! A Michelin star restaurant with an amazing rooftop- views of the skyline AND access to the boutique hotel pool right in the middle of the tables! If you're not into Peruvian, check out one of the equally amazing sister restaurants in West Loop- Girl and the Goat (upscale American), Duck Duck Goat (Chinese), or Little Goat Diner (great brunch).
Eataly Chicago
If you love Italian food, this is the place. Not only are there four Italian restaurants and a couple bars inside, but the whole thing is a huge Italian market where you can browse wine, charcuterie, pasta, and all things Italy while you wait.
Michigan Avenue
Fun fact: Dion and I came to Chicago to visit friends and attend a festival before we were officially dating, and he asked me to be his girlfriend in the Top Shop on Michigan Ave! Little did we know we'd be living together a couple blocks away four years later :)