Chicago Travel Diary

I feel like I say this at the top of just about every travel diary post, but we were over the moon excited to travel to Chicago. It had been high on our bucket list for years, and it was time we finally made it happen!With three full days to explore the lively city, we hit the ground running every day in an effort to cover as much as humanly possible (no surprises there). Between the delicious food (hi, deep dish pizza!), stunning architecture, and thunderstorms that came out of nowhere, we were constantly entertained by all that the city had to offer…and infinitely grateful that we packed rain jackets.

Keep on reading to get all of my recommendations!

We stayed at the Chicago Athletic Association and absolutely loved it. As if its location right next to Millennium Park weren’t enough of a selling point, it also has a Shake Shack in the lobby. Yep, you read that right. Plus, by staying in the hotel, you get the perk of being able to head up to their popular rooftop bar, Cindy’s, at any time. More on that below!

Architecture River Cruise: This was the absolute best way to start our trip. Even though it was a little rainy during our cruise, we got an amazing lay of the land of downtown Chicago and felt so much more informed walking around during the remainder of our trip. I’d highly, highly recommend making the time (and spending the money) for this!

Lincoln Park: This park is so lovely, and the surrounding neighborhoods are too. We spent roughly half of a day making our way through the Conservatory, the Zoo, and finally to some shopping at Halsted and Armitage (more on that below in the ‘Shop’ section).

Millennium Park: Directly across the street from our hotel, we spent a lot of time both in this park, as well as observing it from our room. The Cloudgate sculpture (aka The Bean) is seriously cool in real life and we somehow managed to get a photo with no one else around. I still don’t know how we did that, but I’m so thrilled we did!

Art Institute: Just a block from Millennium Park is the spectacular Art Institute with a notable collection of Impressionist and Modern art. Though you’ll likely start in one of those two places, I’d also recommend heading downstairs to the miniature rooms section—it’s a little hidden gem!

The 606: Big fans of any sort of highline, we were eager to check out Chicago’s version. We started near Logan Square and ended in Wicker Park, where we got delicious smoothies and hung out listening to the cicadas buzz in the trees. It was a really peaceful end to the day and more than ensured that we got our step count in for the day.

Wrigley Ville: While there were no home games happening during our stay, we still made a point to head out to Wrigley Field to see the stadiums and buy Cubs merch. I’m now the very proud owner of a little boy’s baseball tee 🙂

Lake Michigan: It was v hot most days we were in town and if we had had any more time on our hands, I would have definitely spent it sunbathing along Lake Michigan. It’s so stunning!

Skydeck at the Willis Tower: Having learned all about the magnificent engineering behind the Willis Tower (formerly known as the Sears Tower), we were really excited to head to the top on our last day. In retrospect though, I would say that you should skip this tourist attraction. Even though we purchased tickets online for a specific time window, we were forced to wait in line for 3 hours. Since we got there pretty early in the morning, we were able to swing it but it was one of the most disorganized, tiring travel experiences I have ever encountered. And to add insult to injury, our photos didn’t come out *that* great in the end. Save yourself the headache and skip it!

Miracle Mile: There are shopping opportunities galore along Miracle Mile, but I particularly enjoyed the local shops to Chicago, including Ikram and P.O.S.H.

Jayson Home: We were nothing short of obsessed with this design store. It’s a miracle I didn’t leave with two coffee tables, three rugs, and four candles.

Halsted and Armitage: Just a few blocks from Lincoln Park, this area of Chicago is filled with great shopping, delicious restaurants, and beautiful surrounding homes. Seriously, try not to take a photo of just about every house you pass on the side streets.


The Allis at Soho HouseSituated in the heart of the West Loop, this breakfast spot is très chic. Highly recommend coming here for the avocado toast and staying for the vibes.

3 Arts Club and Café at Restoration Hardware: All I can say is “wow,” and that goes for not only the design of this place but also the crowds. If I could have done it over, I would have popped in a couple hours after they open, picked up an iced latte from the bar, and then walked around the property. Trust me, that’s the way to do it.


Portillo’s: Speaking of a crazy busy restaurant, Portillo’s was the definition of hectic. But the hot dogs were good, so I’ll give them that!

Parson’s Chicken and Fish: A favorite amongst locals, this was the perfect spot to come for a refreshing afternoon drink.

Pequod’s and Giordano’s: Going to Chicago without eating deep-dish pizza should be a crime. We heard so much about both of these places and had to experience them both for ourselves.

Summer House Santa Monica: Though we didn’t actually eat here, I thoroughly enjoyed its décor and was sincerely tempted by their cookies.


Ema: AKA the Mediterranean meal of my dreams. The cherry on top? Once you’re done with dinner, you’re smack dab in the bar scene and can pop into a couple to see what they’re all about.

Girl and the Goat: I read about this spot in nearly every Chicago guide I could get my hands on, so I came in with very high expectations. While it didn’t quite live up to the hype in my book, it was still a delicious dinner that I would recommend. Just maybe don’t go in expecting to be blown away 🙂

Au Cheval: My top priority next time I visit Chicago will be getting the burger from this spot. Given that the wait was 3 hours in the middle of the day, I’m guessing it must be pretty damn good…


Guthrie’s Tavern: This nondescript bar was maybe one of my favorite places we visited during our trip. We popped in after our visit to Wrigley Field and got a little tipsy while playing board games—what more could you ask for?

Cindy’s: Located on the rooftop of our hotel, this trendy restaurant boasted amazing views of Millennium Park and delicious drinks. The lines to get up to the top on Friday and Saturday were out of this world, so definitely make a reservation if you’re not staying in the hotel.

Cherry Circle Room: Also located in our hotel was this gem of a restaurant. We frequented the bar and were obsessed with just about every last detail in the place.

Well, there you have it! A whirlwind itinerary of the windy city. We had the best time exploring many corners of Chicago and can’t wait to come back someday.

Have you been to Chicago? Please share your favorite spots below!

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