Chicago Recap

It’s been a few weeks since we got back from Chicago and I already can’t wait to go back!

A few weeks ago, Chris and I headed to Chicago for a few days with his parents and it was absolutely AMAZING. The main point of our trip was to see Hamilton (which was amazing, BTW) but we got to squeeze in time with his college friend, eat a boat load of food, and enjoy the sights. We flew out of Boston Friday morning and flew back Monday night, so we got a solid few days to check a few things off our “must do” list! We did fly into O’Hare and ubered into the city, which was super easy. We opted not to rent a car and just ubered/taxied whenever we needed to, but also walked whenever we could!

Where We Stayed

We stayed at the gorgeous Palmer House Hotel, which is conveniently located on the same street at CBIC Theatre (where we saw Hamilton). We were immediately greeted by a gorgeous lobby, high (painted) ceilings, and the most helpful staff. The location was extremely central to all of the activities we wanted to do and it was nice to be so close to Starbucks (located on the lower level of the hotel).

A victim to the Great Chicago Fire just 13 days after the grand opening, the Palmer House Hotel welcomed its first guests in 1873, making it the nation’s longest continually operating hotel. The hotel has seen hundreds of famous guests, recently underwent a $170 million renovation, and is an extremely popular wedding venue (we saw two over our weekend stay!).

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palmer house hotel lounger


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the palmer house hotel staircase


What We Did

Although a majority of our trip was spent eating, we did stretch our legs a bit!

Lagunitas Brewing Company – I honestly hadn’t even heard of Lagunitas beer until we went to the brewery for a tour! The brewery itself was super cool and not like any of the other breweries I’ve been to. With neon lights, 70’s-esque decor, and delicious beer, the brewery was a great way to spend the afternoon.

wndr museum – Located in the West Loop, the wndr museum just opened in early fall, the museum offers gorgeous installations that incorporate art and imagination. Even though it’s a small space, exploring the different areas of the museum was so much fun!

lagunitas brewery

Hamilton – Okay guys, I need to be honest with you. I never had any interest in seeing Hamilton and didn’t think I’d like it. BUT, when Chris mentioned getting tickets for his parents for Christmas and going on this trip, you bet your bottom dollar that I invited myself. Turns out the play is FREAKIN AMAZING and I’m so glad I had the opportunity to go (thanks, babe!). I highly recommending checking it out if it’s in your city or if you’re planning a trip to a city where it’s playing!

Magnificent Mile – Second to Hamilton, walking Magnificent Mile was one of my favorite parts of the trip, even though it was cold AF. Walking around and exploring new cities is one of my favorite parts of traveling! It was fun to walk around, pop into a few stores, and experience the river before heading to Hamilton.

exploring the magnificent mile

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millenium park


360 Chicago – Any time I can get some cool views of a city, I jump all over the opportunity and on our last day, we headed to 360 Chicago to do just that. Located on the 107th floor, the observatory gives you 360 degree views of the city complete with a glass lookout where you can see all the way down to the street. Freaky. Only downside? You get a very short amount of time to check out the views and take your photos (60-90 seconds depending on your group side).

Millennium Park – When in Chicago…… take a photo in front of The Bean. During our visit, we actually stopped by twice and learned a lot about it after doing some Googling. Did you know that there are cleaners that come twice a day to clean the entire thing? It was also built with Chicago’s skyline in mind so that visitors to the art installation could be in a photo with a majority of the skyline still in view. GENIUS.

Where We Ate

Fair warning: we ate a lot while we were in Chicago

Vapiano – Our first stop in Chicago, we stopped into Vapiano for a quick bite once we landed and dropped our bags off at our hotel. Located literally right across from our hotel, the whole “grab a card, order your food, scan card” thing confused the crap out of me. Once we ate and left, I *finally* started to understand the concept. We got pizza and a caprese salad. Would rate 4/5 stars.

Girl & The Goat – Holy freakin’ delicious. First of all, I never thought I’d ever eat goat in my life, ever. Just thinking about their eating their cute little faces makes me want to cry. But IT WAS SO GOOD. The family style tapas restaurant is located in the Loop and has a cozy, romantic atmosphere. We opted for 8-10 plates to share among the four of us (not including dessert), which was more than enough. If you’re heading to the city, I definitely recommend checking it out!

What we ordered: goat empanadas, confit goat belly (pictured below), pan fried shishito peppers, grilled beef short ribs, crisp braised pork shank, spiced shrimp, sautéed green beans, roasted cauliflower, caramel corn & malt balls, and sticky tasty crunchy toffee yummy cake

palmer house hotel lounger

Goddess & The Baker – CUTEST SPACE EVER. Every detail of the space was clearly well thought out – from the gorgeous mid-century modern furniture to the organization of the pastry shelves. We stopped into Goddess & the Baker for a quick breakfast on Saturday morning and it was delicious! I opted for the pepper and egg sandwich and a coffee, while Chris had avacado toast, a slice of carrot cake (which was ginormous BTW), and a black honey almond matcha latte.

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coffee the goddess and the baker


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pastries the goddess and the baker


the goddess and the baker

Luxbar – After dinner drinks are always a good idea and heading to Luxbar to do just that is the perfect way to end the night. The American bar is known for it’s checkered floors, jazz music, and apparently has the best Manhattan, ever (I got a glass of wine so I cannot confirm).

Rosebud – One of Chris’ dads favorite spots, we headed to Rosebud’s for dinner Saturday night and we had ourselves a FEAST. I have to say – the Italian restaurant has delicious veal velasco and a damn good chocolate cake, which was bigger than my head.

Cindy’s – Roughly 294702957 people suggest we go to Cindy’s, so we went twice. Once at night for drinks and then lunch on our last day. Located within the Chicago Athletic Association, Cindy’s is a rooftop restaurant with gorgeous views of Michigan Ave. and Millennium Park with delicious eats. It is on the expensive side so I highly suggest going during the day for a meal to experience the atmosphere and pop in at night for a drink and to see the city lights.

What we ordered: Cindy’s house salad, beat & avocado salad, prime skirt steak, roman gnocchi, chicken parmesan, s’mores baked Alaska, and the taffy apple tart.

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cindys rooftop bar


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cindys rooftop gnocchi

Three Dots and a Dash – Hands down one of the coolest bars I’ve ever been to, Three Dots and a Dash is a speakeasy-style tiki bar with retro Polynesian-style decor. SO FREAKIN CUTE. But if I’m being totally honest, I wish I wasn’t as exhausted as I was so I could enjoy it more. The mai tai was also a little too sugary for my liking and have an extremely sensitive stomach, so I obv got the worst stomach ache after. BUT with that being said, I am 100% going back on my next trip.

Corner Bakery – Located on the corner of the Palmer House Hotel building, the corner bakery is literally on the corner of E Monroe and S Wabash and was the perfect spot for a quick bite. The coffee was also delicious and the cinnamon bun… brb I’m drooling.

Pizano’s – You have to get deep dish at least once while you’re in Chicago, right? We opted for simplicity and ordered the sausage deep dish and it did not disappoint. The interior was also so cute, cozy, and filled with Christmas decorations. Does it get any better?!

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Have you ever been to Chicago? Let me know what your recommendations are for my next trip in the comments!

Leave a Reply


  1. 11.26.18

    Yay! So glad to hear you loved Chicago and you thankfully made it before the first snow, which just happened last night! Looks like you did so many awesome and iconic things and the hotel you stayed at is one of my favorites!

    Denise | Fashion Love Letters

  2. 11.26.18
    Liz said:

    Chicago looks like such a dream! I’d love to go someday!

  3. 11.26.18

    What fabulous pictures – looks like you had an amazing trip!!

    xoxo Sarah

  4. 11.26.18
    Lee said:

    Chicago has been on my “must visit” list for ages! I so need to go. Looks like you had a great time!

  5. 11.27.18

    What a fun trip! I flew in to Chicago a few weeks ago but sadly didn’t get to explore. Cindy’s looks like a place I need to visit when I go back 🙂

    -xo, Azanique |

  6. 11.27.18
    Jessica said:

    Chicago is one of my favorite cities to visit! There is so much to do and eat!
    xo Jessica

  7. 11.27.18
    Em said:

    I am dying to go back to Chicago soon (only when it’s warmer haha!) Looks like you had a great time!

  8. 11.28.18
    Cindy said:

    What a great review of a memorable time spent together! Loved every minute. Great city.

  9. 11.28.18
    Laura said:

    I looks like you had a fabulous trip!! I definitely want to visit Chicago someday!

    xo, Laura

  10. 11.29.18
    Nailil said:

    I absolutely love Chicago and can’t wait to go back.

    Xx, Nailil

  11. 11.29.18

    I want to go to Chicago just to eat all of that food! I’ve never been to Chicago and I can’t wait to go!

  12. 11.30.18
    Avani said:

    Can you believe, I’ve never been to Chicago before! I need to visit there soon.. will surely keep your guide handy!