Chicago, Illinois Travel Blog
Food | Stay | Entertainment
Chicago has quickly become one of my favorite cities to visit. You get the best of both worlds with having the city life, but also amazing beaches with fresh, clear water, something you definitely cannot get in NYC. Here are some of my favorite eateries, entertainment, and places to stay in Chicago, Illinois:
Food
RAISED | An Urban Rooftop Bar: Located inside the Chicago Renaissance Downtown Hotel.
We ordered the garlic ciabattas and their french fry tower which were AMAZING! The drinks were also very good and the service was exceptional. The vibes inside were also a 10/10. They have a very cute inside ambience and you’re also able to sit outside on the rooftop and get a gorgeous view of the city.
Bandit: Located in the West Loop. This spot was a high-vibe, eccentric bar that really scored aces for the atmosphere. We ordered food and did bottomless brunch, which was $35 for 2 hours. The best part about bottomless was not having to ask the waitress once for a refill because she was on top of it. There was a DJ but the music was really low, you really had to tune in to hear each song (my only complaint).
Giordanos - Home of the Deep Dish: You can find one around every corner basically.
We couldn’t come to Chicago and NOT dry the famous deep dish pizza. The deep dish took about 45 minutes to an hour to come out so sip on a few drinks and order an appetizer while you wait. Coming from New York, I knew it wouldn’t compare, but it is always fun to try new foods!
Tao: Located a few blocks away from the Magnificent Mile. If you read my New York Travel Blog then you’ll know I am a huge fan of this establishment. I had high expecations going in considering how amazing the uptown location in NYC is and I have to say the aesthetic of this chain is phenomenal. The interior is gorgeous, the vibe is spectacular, and the cherry on top was that they played good music, not loud enough where you can’t hear your conversations at dinner, but also not low enough where you can’t hear it at all.
Stay
21C Museum Hotel: located right near the Magnificent Mile and Chicago’s Riverwalk. I have to say, this is by far one of my favorite hotels I’ve ever stayed at (I love a good boutique hotel). The rooms were spacious, clean, and modern. My ONLY downside is the room amenities lacked a refrigerator and a microwave, but we made do without. The hotel iteself is located above an art museum. The first two floors have beautiful art exhibits and they even had live music in the lobby one evening. My travel hack (thanks to TikTok) led me to find @hotel, a third-party booking platform that provides discounted prices for stays around the world and we saved $200 for this trip!
Entertainment
ROOF on theWit: Located at the Hilton Hotel.
Unfortunately, they had a $20 cover charge for non-hotel guests (I thought we got rid of cover charges a long time ago, gross), but the rooftop area was gorgeous. It was not huge, but not too small either and the crowd was very diverse. My advice, pre-game before you arrive as one shot (house liquor) was $25.
Another thing you HAVE to do in Chicago is see the famous Bean at Millenium Park. The park itself is beautiful and clean and there are a lot of establishments in the surrounding area.
The NOW Massage: Located in Lincoln Park. There are three locations in Chicago (the other two being in the South Loop and Lakeview).
I always try to make time for a little bit of wellness when I travel. We booked their 80-minute ‘The Healer’ massage which was an energy balancing massage focusing on mind, body, and spirit for $145. The place was very cute and zen and they offered beverages and additional add-ons.
Chicago is also known for its beaches! I really didn’t know what to expect the beach to be, especially being on the outskirts of the city. We first stopped at Navy Pier, which had a strip of places to eat and drink before you get to the carnival rides, games, and just an overall super cute venue. We just had to take the ferris wheel which showed us amazing views of the city, it was honestly breathtaking and a highlight of our trip.
