Chicago Food and Sights – A weekend getaway

Chicago Food - Cindy's Rooftop view

I almost forgot what a fun city Chicago is to visit! From Minneapolis, it’s only a 6 hour drive or 45 min flight making it a perfect little weekend getaway. As the years go by, and as my tastes and interests have grown, it’s been so fun to go back to these cities I visited when I was younger. Speaking of TASTES, Chicago food is some of the best! Travis and I have done a good amount of traveling in the last couple years and I have to say I’ve gotten good at researching and planning trips, from big to small! If you’re looking for ideas: restaurants, sights and things to do – here it is.

Since this was a short trip, we chose to fly via Southwest airlines, which offers early morning flights for cheap. We took a 6am flight on Saturday morning of labor day weekend. It was a little rough getting up so early to get to the airport, but I have to say it was so nice to have the entire day ahead to explore! And bonus, you can save the money for that extra night of a hotel stay and put it towards food or shopping!

*Side note: this post is not sponsored. I’m sharing the details of our trip just because I want you to have a fun experience and get good deals too! Enjoy!

We stayed at the Cambria Hotel in the Loop / Theater district of downtown Chicago. The location was PERFECT. Walking distance to tons of sights and restaurants, which helps you save on uber or train rides. The hotel was awesome. They let us check in super early (8am!) which was great for our early flight.

Chicago Food

Our first stop was breakfast/brunch and I had read about a cute cafe called “The Lula Cafe,” a little ways out of downtown. We took the train to Logan Park, which was super easy to do. The cafe has a trendy hipster vibe, with great coffee and creative brunch food. We had a just a few minutes to wait at the bar with a coffee before we got a table. Travis got the breakfast burrito and I got the sweet corn & grits with cherry tomatoes, parmesan and a slow-cooked egg. So good!

Another restaurant I had read about online was called Au Cheval, known for their amazing burger. I had read to expect a long wait, but we were still totally taken off guard by the wait time!! Any guesses? For a table of four our wait was….. 6 hours!!! What?! We couldn’t wait that long for dinner, so we headed across the street to get some appetizers at the tavern. Then explored the areas cocktail bars for drinks and had a great time, forgetting all about Au Cheval. As we’re walking home for the night (it’s after midnight), we get the call that our table is ready! So funny. By then, we could all eat again so back to Au Cheval we ran for the best burger I think I’ve ever had in my life. Yes, it was that good. My advice, get to the restaurant 30 minutes before they open and wait in the line outside, or be prepared for a ridiculous wait and have a plan B. Whatever you do, make it happen. This burger is BOMB. (PS – yes that is bacon!) 

Chicago Food - Au Coeval is the best burger!

When you think of Chicago food, you probably think of deep dish pizza. But honestly, it’s not my favorite style of pizza (I know, how can you be in Chicago and not get that?), but we’ve been there, done that. So we decided to get a good authentic Italian, Neapolitan style pizza. I’d read great things about Spacca Napoli, a little pizza place tucked away in a neighborhood a little north of downtown. We hopped on the train and I heard a group of people talking about how great Spacca Napoli is! A great sign. This cute spot has a patio and the inside is adorable. It was super hot so we ate inside. Appetizers, salad and pizza were all delicious!

At the top of the Chicago Athletic Association Hotel is a gem of a restaurant, Cindy’s Rooftop. Right on Michigan Ave, this place has the BEST view. Large windows and garage doors that open into the view of Millenium park, the bean and downtown skyscrapers. It’s a must-see! Going into it, I thought this place was all about the view and therefore the food would be mediocre. I was so wrong! The food was AWESOME.

*Side note: there was a wait to get up to the rooftop. The line starts in the lobby of the hotel near the elevators. We stood in line for 10 minutes before they opened for lunch at 11am. A few minutes after we sat down there was not an open table in the place! They DO take reservations.

THE FOOD: Bison Burger with beet ketchup and kale + sweet potato fries was to die for. I got the goat cheese tartlet which was also amazing!

THE VIEW: speaks for itself!

Chicago Food - Cindy's Rooftop downtown view

Chicago Food - Cindy's Rooftop view

Chicago Food - Cindy's rooftop, buffalo burger brunch

I’m always in search of cute coffee shops with good quality coffee rather than going to a starbucks. We stumbled upon the coolest coffee shop as we were waiting for our table at Cindy’s. In the lobby of the same hotel is a coffee shop called FairgroundsThis is probably the coolest coffee shop I’ve ever been to! They brew craft coffees from all over the country as well as nitro coffee and cold brews on tap. You can get a coffee flight and try multiple coffee flavors too! If you know me at all, you know I LOVE spyhouse coffee and Fairgrounds had spyhouse coffee! So cool!

Chicago Food - Cool Coffee Shop

Chicago Sights

Some things to do in the city:

  • Walk along the river
  • Shop
  • Walk and eat in Navy Pier
  • Rent bikes and bike the city
  • See a show

Chicago Food & Sights - River view

Chicago Food & Sights - skyline view

Stay tuned for a post about our recent New York City trip! For other weekend getaway ideas see my post on Denver.

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