Chicago is literally such a fun city for me to visit, and this trip was my first time coming in Feb/Winter! If you are new here, my husband, Andrew, goes to Chicago two times a year for work. These past couple years, I have been able to tag along on his trip, which is SO fun. Because it is a work trip, I am often by myself 85% of the day. Exploring and doing all the girly things is my JAM. Last year, I got my favorite hot pink Dior Saddle bag, which is such a wonderful memory.
Every trip, I like to try new restaurants and experiences, so my list of Chicago favorites definitely grows. If you are going to Chicago soon, definitely look at my other Chicago trip posts to get a good idea of what to do. As always, please message me on Instagram (or email me kellyruthhans@gmail.com) for any help with planning your itinerary!
This trip, we stayed at the newly renovated Holiday Inn Wolf Point. This hotel is connected to The Mart, which is where Andrew has work so it is insanely convenient. There’s not a lot of restaurants/shopping there, but if you don’t mind walking an extra 10 minutes places, it’s a great location. The hotel was amazing and super friendly staff. They don’t offer free water for guests (which is such a crime, in my opinion), but a hack is to fill up a water bottle in the fitness center (always free).
Blue Door Kitchen and Garden: We had brunch here and it was not only super cute, but great food and mimosas! Great location to walk around after, too. I ordered the Omelet and my friend ordered the Avocado Toast. SO yummy. They have an “outdoor” seating area, which is really just a greenhouse style patio. SO adorable.
RPM Italian: Chicago has several of these restaurants, all with different cuisines (seafood, steak, Italian). This restaurant was so nice and the atmosphere was awesome. They also offered SEVERAL Gluten Free pasta dishes and main courses. 10/10
Shaw’s Seafood: This is a repeat restaurant for us. We have to go every time, it’s just that good! Amazing seafood and sushi. Great atmosphere and vibes. Its a classic Chicago staple that has been around for decades. Super cute date night spot, too!
Cindy’s Rooftop: Okay… this was a curveball, spontaneous, spur-of-the-moment restaurant for me. Might have been my favorite restaurant I went to in Chicago. It is inside a hotel and the views are OUTSTANDING. This is a must go to for any trip. I went for brunch and had no reservation, but was able to walk in on a Saturday morning. The breakfast was super good. This would be a fun place for cocktails in warmer months because of the rooftop terrace. Restaurant is located right in between the Bean and The Art Institute, so easy to make a day trip out of.
Hampton Social: There are a few locations downtown Chicago. Super cute coastal vibes and we loved the food and drinks. For a drink, I got a drink called “I Glitterally Cannot” or something like that. It was similar to a Cosmo and had edible glitter. Super cute!
Goddess and the Baker: If you are looking for a good coffee/bakery shop, this is it! Tons of locations downtown Chicago and super good! I got the avocado toast on gluten free bread and it was heavenly! Lots of GF/DF options to try, too.
Art Institute of Chicago: This is a classic thing to do when in Chicago, and this was my first time going. It is literally so massive and one could easily spend some good time in there. I am a browser when it comes to museums… I don’t like to read every single plaque. So it took me about 2-2.5 hours, which is perfect for me. Lots of cool paintings and I really liked the Egyptian wing!
Millennium Park/The Bean: Another must do in Chicago that I had yet to explore! This is definitely a cute place to take pictures… but for the every day tourist like me, I saw it… took a few pictures..then went on my way to the Art Institute (right next door). 5 minutes tops. But still a great thing to see!
Shopping: I love shopping down Michigan Avenue. So many fun designer stores to pop into as well as a great Zara and H&M. Chicago also has a super cute brand called Alice & Wonder that sell really cute city of Chicago gear. Right next door is this adorable gift shop called Posh that has the cutest things (and lots of French items)!
This trip, I also got to meet one of my OG blogging friends who lives Downtown Chicago! Literally so wild! We have been Instagram friends for at least 5 years… probably more! It was so great meeting her IRL!
Chicago in February is COLD. Pack lots of layering pieces and coats
Chicago is extremely walkable. I only ordered an uber one time becasue it was early in the morning and literally 20 degrees (30 minute walk). But once the sun came out, I ended up walking all around and back to hotel.
Fleece Lined leggings literally are a game changer. I was actually warmer wearing these than anything else…and they looked cuter!
Streets that I feel super safe walking on are: State, Michigan Ave, and Dearborn. I try to stay on those if I can.
My tip with nicer bags: I do cross-body and put my coat on after I put my purse on. No fear!
Outfits I Wore:
LTK Posts:
Chicago is a super fun city to visit and I always have a good time. If you’ve been, what are your favorite places or things to do?
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