Friends! Oh my gosh it’s been awhile since I’ve posted a travel guide, in fact it’s been exactly 3 months! We traveled straight from Charleston to Chicago (and stayed for THREE MONTHS)!!! It was literally one of my most favorite places we’ve lived for so many reasons that I’ll get into. This was one of our most unique stays because were able to live through quite a few seasons- we caught the tail end of Summer (since we arrived September 1), and then were able to experience Fall (it was short lived but SO AMAZING), and then left Chicago December 1 (so it felt like winter)! Our last time here (see my Chicago travel guide) was in in the winter, January of 2021 (when unfortunately everything was pretty much still shut down from the pandemic), so getting to experience OPEN Chicago was truly so incredible and I don’t have enough good things to say about it! I think my love for the city shined through the content I shared on Instagram 🙂 Let’s get right into my updated Chicago travel guide…

WHERE TO STAY:

Again, we stayed with Suite Home Chicago and rented a 2 bedroom/2 bathroom unit in one of their apartment buildings and I could not recommend staying with them more (see my apartment video tour here)! They really know how to accommodate travelers and make it feel like your home away from home. We stayed in a new apartment building this time (which we preferred) since it was RIGHT next to Michigan Avenue and the River. It was truly the most convenient and BEST location- we walked everywhere!! To be specific, we stayed at the Optima building on Illinois St. which had a great pool, amazing gym, very nice and welcoming front desk staff, and my favorite part- was right above Whole Foods 😉 Definitely check them out if you’re planning on living or visiting Chicago!

WHAT TO DO:

Definitely check out my originalChicago Travel Guide where I share all the things we did last time we visited, so just to update the list, here is what we did this time around while staying in Chicago for 3 months:

Architectural Tour (#1 recommended thing to do in Chicago)

Visit and walk around the Gold Coast- Oak Street shopping!

Take a stroll through Lincoln Park- absolutely gorgeous especially during the Fall!

Ferris’s Wheel at Navy Pier

Starbucks Reserve- 4+ story Starbucks that serves cocktails + food

Michigan Avenue (all the shopping)

Lincoln Park- ride bikes around Armitage Street then ride around and look at the stunning houses

Take a bike ride along the Lakefront Shore Bike Trail (we did this almost daily it was our FAVORITE)

Millenium Park- go check out the Bean (super neat art installation)!

Walk or ride bikes over to West Loop- up and coming area of Chicago

Ride bikes or take a long walk along the 606 (similar to the high line in NYC)

Go to a Chicago Cubs game at Wrigley Field (so much fun!)

Ribbon Ice Skating (of course this is only in the winter but amazing!)

Go to a concert at House of Blues Chicago- so fun!!

If it’s warm enough- go to the beach at Oak Street (so fun to jump into the lake)

WHERE TO EAT/DRINK:

BRUNCH/COFFEE: 

Ralphs Coffee

Foxtrot- these are everywhere around the city, my favorite one is on Armitage where you can sit outside

Collectivo- specifically the one on Clark St- it has the BEST outdoor patio, firepit, everyone is reading/chatting/hanging out, it’s the best vibes- we went here every weekend!

Real Good (get their housemade almond milk)

Kanela-my favorite omelette I’ve ever had

JuicerX- my favorite smoothie shop

Beatrix- I recommend the West Loop location

Burrito Beach- quick/easy spot to grab breakfast burritos

Summer House- this is a very trendy brunch and dinner spot!

DRINKS/DINNER: 

Carmine’s- an Italian food, Chicago classic!

Avli on the Park- incredibly aesthetically pleasing greek/mediterranean dinner

Tuco and Blondie- delicious Mexican food!

Happy Camper- a little of everything here, good pizza, fun vibes!

Siena Tavern- great Italian dinner right downtown

Smith and Wollensky Steak House- fancy dinner spot along the river

Roka Akor- modern asian food (so so delish)

Roberts Pizza- truly a hidden gem! it’s a delicious pizza spot RIGHT on the river

Big Bowl- easy Thai/Chinese takeout (my favorite is the Chinese chicken salad)

Nonnina- charming Italian spot right downtown

Hampton Social- lively spot for dinner/drinks

Wildfire

DESSERT:

Jeni’s Ice Cream- this is a must!

Ingrained- vegan, organic, gluten free, refined sugar free desserts

OTHER THINGS TO NOTE:

• My favorite workout studio in town is: Bodyrok (I actually ended up getting a membership and am hooked. It’s lagree form pilates and the instructors are amazing)
• Zazu Salon was where I recommend getting your hair done!
• Definitely consider getting the DIVVY app for bike riding around town! This saved us SO MUCH without a car. It was so fun to ride along Lakeshore Drive Bike Path (it’s over 16 miles along the lake and absolutely BEAUTIFUL). Definitely a highlight for us the 3 months we visited!