The Weekend Guide To Chicago

A couple weeks ago, I went to Chicago with my boyfriend for his birthday. I had surprised him with plane tickets for Christmas and we had been looking forward to it ever since. Unfortunately we were only able to go for a long weekend (#adultlife), but we were luckily able to squeeze in all of the main attractions and lots, I mean LOTS, of food.

We arrived early morning on Friday, which gave us about three days to sight-see and do activities until our flight back to LA on Sunday evening. Before going, I had done tons of research and talked to quite a few people from Chicago about recommendations on what to do and where to eat. We had a pretty solid list and made sure to check everyone off while we were there.

I don’t know if you know this about Chicago, but it has some incredible food. It was actually kind of crazy. My boyfriend and I would look at each other with a face of “this is the best thing ever” during every meal and were in total disbelief when one restaurant surpassed another on how delicious it was. While I wish I could tell every detail of my trip and how amazing it was, I wanted to share the main highlights of the weekend. The next time you are in Chicago, even just for a few days, you have to check out the below:

Things to Do:

Willis Tower: If you don’t know, The Sears/Willis Tower is the second tallest building in the United States. On the 103rd floor, they have the Sky Deck where you can get 360 degree views of Chicago. There sometimes can be a wait (we had to wait over an hour and a half to get to the top) so it’s best to plan ahead and give yourself plenty of time to spend there. The employees at Willis Tower informed me that Saturdays are their busiest days, and it’s best to go first thing in the morning. This is definitely a sight worth seeing, but it is important to plan for it in advance.


Millennium Park: Millenium Park is a beautiful park right along Lake Michigan. Most people know it because it is home to Cloud Gate, or The Bean, but it also features the Jay Pritzker Pavillion as well as Wrigley Square. It is a wonder place to walk around, enjoy the views of the city, and take in all of what Chicago has to offer.


Magnificent Mile: Magnificent Mile is located on the famous Michigan Avenue. It is a 13 block span of over 450 stores ranging from luxury to fast-fashion to specialty to food. Essentially, it is the “5th Ave.” of Chicago. Even if you aren’t in the mood to shop, I still recommend walking around Mag Mile just to see the beautiful architecture; the skyscrapers are some of the most breathtaking I have ever seen.


Navy Pier: If I were to go to Chicago again, Navy Pier would be at the end of my to-do list. While it is great in the summer with it’s ferris wheel and small carnival attractions, there really isn’t that much to do. The views of the city from the pier are beautiful, but you do not need to allot much time visiting here.


From the top of the Willis Tower


The Bean in Millennium Park


The ferris wheel at Navy Pier


Views from Navy Pier


Food & Drink:

Au Cheval: If you go to Chicago and skip Au Cheval, you won’t only be letting me down, you’ll be letting yourself down. This was hands down the best burger I have ever had; I literally told all of my friends it was life changing. They are known for their cheese burger and adding both an egg and bacon. I normally don’t like bacon burgers, but I listened to the waiter and had zero regrets. If you want to have your mind blown and eat one of the the best burgers in America, please go to Au Cheval.

Girl And The Goat: If you are adventurous and willing to try new foods, then Girl And The Goat is a must. They serve items like goat shank, beef tongues, and duck tartare, which may sound strange or gross, but everything was beyond incredible. I recommend getting the pig face and goat belly. They were each delicious in their own way and so decadent. I’ll be honest, I was nervous about the goat; I had never had it before and had no idea what to expect. It was actually so tender and full of flavor; I would go back to Chicago just for that dish. We finished off the meal with Caramel Corn & Malt Balls, which was vanilla malt ice cream coated in chocolate and topped with bits of caramel corn. Yes, it was as heavenly as it sounds.


Gibson’s: If you are wanting a nice steak dinner with old-school vibes, Gibson’s is your place. They have been around since 1989 and are known for their high-quality prime steaks. We started with the lobster cocktail, which was served cold with an artichoke and shared a wedge salad. My boyfriend claims this was one of the best salads he has ever had and I have to admit it was extremely fresh and crisp just as a great wedge should be. For our entrees, I had the prime rib (which is one of my favorite foods) and my boyfriend had the t-bone. We also had the loaded twice baked potato to share. Unfortunately, we were so full that we couldn’t even think about dessert, but we heard the pies were phenomenal.


Deep Dish Pizza: To be honest, this was one of my smallest priorities while I was in Chicago. The city’s two most famous deep dish pizza restaurants, Lou Malnati’s and Giordano’s, both have locations in Arizona where I’m from. Luckily, we did have time to grab a slice before we had to leave so we were sure to ask the locals where to go. We decided upon Gino’s East, and it was great quality deep dish pizza. Pequot’s was another recommendation, which I’m sure offers the authentic Chicago pizza experience.


Chicago Dog: It was my boyfriend’s mission to get a Chicago dog all weekend. He didn’t want some fancy restaurant or a chain; he wanted a random street vendor that served up the best dog’s in town. While we were out and about, we were constantly keeping our eye out for a hot dog stand. Finally, we hit the jackpot in Millennium Park; there was a vendor just a short distance away from The Bean. This was our moment. So we got our dog’s Chicago style, no exceptions, and it was well worth the hunt. I can’t say that I’d normally eat “street meat”, but this was a rare instance. I totally recommend getting a Chicago dog with all the fix ins. I promise you will have no regrets.


Cindy’s: While I went to a few different bars while I was in Chicago, Cindy’s is the one worth mentioning. It is located on the roof of the Chicago Athletic Association Hotel and has beautiful views of Millennium Park and Lake Michigan. They serve food here, but the patio is what’s worth going for. They have incredible craft cocktails that you can sip while sitting around a fire pit and taking in all the views. I recommend getting the Kick in The Daisy (a fresh watermelon tequila drink) or the Grey Garden (a refreshing vodka lavender cocktail).

Craft cocktails at Cindy’s


The Chicago Dog


Rooftop view from Cindy’s


Let’s connect! Instagram | Pinterest | Facebook


  1. March 4, 2017 / 2:19 am

    The Willis Tower shot is so cool but I’d be so scared!

  2. September 20, 2017 / 7:11 pm

    What a lovely guide! Visiting Chicago is on my list of places to visit!

      September 20, 2017 / 7:21 pm

      thank you! you definitely have to visit it’s a great city!

Leave a Reply

Your email address will not be published. Required fields are marked *