Summer Weekend in Chicago – 2019 Eats

In my humble opinion, Chicago is one of the best cities in the country to visit. It has fantastic food, friendly people, sports, and museums. The city is at its very best in the summer months when it seems as though everyone is spending every moment outdoors. This year, I visited Chicago in June and lucked out with beautiful sunny weather and cool nights. It was a welcome reprieve from the Florida heat and humidity!


I visited my best friend Emily. One of the great things about visiting a friend repeatedly is that she knew what I had and hadn’t seen and what areas of town might be new and fun to me. On this visit, we spent most of the weekend in the River North and West Loop neighborhoods. I’ve talked about past trips to Chicago in this post and this post if you’d like to read more about Chicago. Even though the trips were 5 and 6 years ago, most of the recommendations are still up to date.

I arrived on a Friday at noon, so our first stop was lunch. We decided that tacos sounded perfect and took a short walk from Emily’s building in River North to Barrio for tacos and drinks. We ordered chips with a selection of three salsas; the salsa verde was my favorite, although I enjoyed the tomato and jalapeno as well. I ordered grilled octopus tacos for my main, which were fantastic! The tacos came in a chimichurri sauce topped with roasted jalapeno, avocado, and potato crisps.

Barrio patio

Our next stop was Cindy’s Rooftop for drinks and views of the city. Cindy’s is a restaurant/bar at the top of the Chicago Athletic Association Hotel. There is a beautiful, airy, enclosed portion of the restaurant, but we spent most of our time on the open-air terrace to take in the panoramic views of Millenium Park and Lake Michigan. We had to wait in a short line to go to Cindy’s, but you can make reservations on Resy.

Cindy’s Rooftop
View from the terrace

One of my favorite activities of the weekend was playing City Mini Golf in nearby Maggie Daley Park (a 5 minute walk from the Bean). About half of the obstacles are Chicago-themed, like Cubs, Bulls, and the Willis Tower. Mini golf is always fun, but especially when it’s in a beautiful setting with locally themed obstacles. We had a blast and it took under an hour to get through the course.


We ended the evening with the most incredible dinner at Ema, a Mediterranean restaurant opened by former Top Chef Duels winner CJ Jacobson. We enjoyed a mezze dinner of shared small plates and tried two spreads, falafel, grilled halloumi cheese, grilled octopus, chicken kefta, and braised short rib. My favorites were the falafel and the chicken kefta, but everything we ate was excellent, even the bread. Chef CJ has another restaurant in Chicago, Aba, which I’m told is also fantastic.

I love trying new workout classes when I visit bigger cities so on Saturday morning, Emily and I took a SoulCycle class. I have been hearing about SoulCycle for years and as an indoor cycling enthusiast, had been wanting to try it for awhile. Honestly, it wasn’t my favorite group exercise class but it was still nice to start the day with a sweat. Since this isn’t a fitness blog, I won’t go into a full review of the class, but generally, I didn’t like that there are no metrics in the class so you have no idea how hard you are working.


Emily had previous plans at lunchtime on Saturday so I enjoyed a solo lunch at Cafe Spiaggia, another Top Chef restaurant where Chef Joe Flamm is the executive chef. I was seated facing the window, where I had views of Lake Michigan and enjoyed a three-course lunch. I started with a perfectly cooked large meatball, had handmade cavatelli with peas, ricotta, spring onions, and ramps for my entree, and finished the meal with a scoop of strawberry balsamic gelato. Everything was delicious, the only thing missing was Chef Joe himself! Before I left, I peeked into the larger Spiaggia restaurant, where I saw the pasta being made. I had a wonderful experience, but my only complaint was that I felt I was tricked into buying a $7 bottle of Evian when I would have gladly drank free tap water.

Cafe Spiaggia
Lunch view over Lake Michigan
Handmade pasta

To walk off my enormous lunch, I walked back to River North down the Magnificent Mile, stopping to shop at Sephora and H&M. When I got back, I rewarded myself with an hour at the pool before meeting Emily for a long walk. We strolled along the Riverwalk where it seemed the entire city was having drinks and enjoying the beautiful summer sunshine. We then walked along Lake Michigan until we arrived at the very impressive Buckingham Fountain. It was donated by a philanthropist as a memorial for her brother. Later that evening, we all guessed at how many jets the fountain has and were shocked to learn that it has 193!


Emily and I at Buckingham Fountain

After getting cleaned up for dinner, we went to the West Loop for dinner/drinks. The West Loop is a popular neighborhood that is known for it’s trendy and high-quality dining options. We ate authentic Italian food at Bar Siena (the sausage and brussels sprout pizza was a standout). Bombolini (donuts) and gelato are sold from a walk-up window on the side of the restaurant. Judging by the line wrapped around the corner, they are worth the wait!


Inside Bar Siena

After dinner, we had drinks at The Hoxton; we started upstairs at Cabra and ended the night downstairs at Lazy Bird. Cabra is a Peruvian Cevicheria with a rooftop pool and bar. I would love to have dinner there on our next trip to Chicago – just reading the menu reminded me of Alex’s and my trip to Peru. Lazy Bird is a slightly more relaxed bar in a library setting with craft cocktails and live music. The musician performing when we were there did a medley of Disney hits and other sing-along favorites. It was a great way to end the night!

Upstairs at Cabra

On my last morning in Chicago, we walked to Meli Cafe for brunch and strolled along the RiverWalk before I headed to the airport for my flight home. Thank you so much to Emily for being the best host! I had such a great weekend in Chicago and cannot wait for the next visit!

Farewell until next time, Chicago!

Barrio, 65 W Kinzie St, Chicago, IL 60654
Cindy’s Rooftop, 12 S Michigan Ave, Chicago, IL 60603
Ema, 74 W Illinois St, Chicago, IL 60654
Cafe Spiaggia, 980 N Michigan Ave #2, Chicago, IL 60611
Bar Siena, 832 W Randolph St, Chicago, IL 60607
Hoxton (Cabra and Lazy Bird), 200 N Green St, Chicago, IL 60607
Meli Cafe, 540 N Wells St, Chicago, IL 60654

City Mini Golf, 337 E Randolph St, Chicago, IL 60601
Buckingham Fountain, 301 S Columbus Dr, Chicago, IL 60605

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