Two weeks after hubby and I got married, we headed to Chicago for a four-day weekend. Chicago was pretty high up on our list of cities to visit because we enjoy architecture, walking through cities, and eating good food. We definitely could have spent weeks if not months exploring Chicago, but we did try to fill up our four days while we were there with the best of Chicago, Illinois sights & bites. If you’re not sure where to eat when you are in Chicago, below is a list of some of our favorites.
CHICAGO EATS
Jam and Honey:
I had no idea that most restaurants in Chicago are BYOB. We went to this delicious space and sat outside with a couple bottles of champagne. The restaurant brought us orange juice so that we could have mimosas. I ordered the Nutella French toast, and hubby had the breakfast burrito. It was a little pricey for the food we received, but the food tasted great and the location couldn’t have been more central (right next to the zoo).
Lou Malnati’s Pizzeria:
Everybody and their ma (in a Chicago accent) told us to try deep-dish pizza, so we did. It basically is thick with a quiche-like consistency, and you actually need a knife to cut through it. This place had an hour-long wait when we got there, and we were hangry, but we waited anyway! Our seats were prime and the service was quick. Thank goodness the food was finger-licking good. The best part was definitely the crust, which is their signature recipe. Bonus, there’s a doughnut shop right next to it, so get yourself a fresh regular glazed doughnut after your pizza. Yummmm.
Asian Mix Cafe:
Hubs and I were so ready for some good Indian food in Chicago, but then we were tempted by the delicious reviews for a nearby Thai restaurant (also we were hangry). We ended up going with the Thai, and oh man was it tom yum yum! I ordered the red curry, and he had the green curry with chicken. We actually had it delivered, and they quickly sent us everything we needed. The pricing was great, and we would definitely order from there again.
Emerald City Coffee Shop:
Right underneath the Sheridan red line stop, you will find this little gem of a coffee shop. We came here one morning for a few breakfast tacos and coffee, and were not disappointed. if you’re not keen on breakfast tacos, their menu has a variety of delicious looking bites. If you get the trivia question right, you get a little discount for your coffee!
Asado Coffee Company:
It seems like most of our money in new cities goes to hipster coffee and unique coffee shops. But we have no regrets about that. Asado Coffee Company is a small hole-in-the-wall coffee shop with a simple menu and, most importantly, great tasting coffee. We started off our mornings here more than once and have zero regrets about that. My husband had a pour-over and I had an Americano. Even though the coffee might be a little pricier than average, the great taste and the friendliness of the staff made it worth it.
CHICAGO EATS WITH SIGHTS
Castaways Beach Club:
One of my friends who lives in Chicago was telling me that due to severely cold winters, any time the sun comes out and the weather warms up a bit, people are out of their minds with delight. The days we were there were warm enough to go enjoy North Avenue beach. We started at Castaways, which is a beach-side party spot with a rooftop bar, frozen drinks, food, and live music. We danced for a hot second, grabbed a few drinks, and then enjoyed the beach. Even in June the water was a tad chilly, but everyone was out there! This is a must-do! Even if you don’t get in the water, I would recommend renting bicycles because there’s a lovely path along the lake.
Cindy’s Rooftop Bar:
After we took plenty of pictures at The Bean, we headed to the Chicago Athletic Association Hotel, which has a hip, stylish rooftop bar/eatery with an incredible view. They have an eclectic list of specialty cocktails and seasonal bites. I will say that it is hard to get seated because there are so many people, but if you head out to the patio area you can wait until you find some seats or stand and enjoy the view!
Trump Tower:
Before the craziness of the election, we visited Trump Tower because it’s a gorgeous and very tall building. Plus hubby is an architect, so we checked out a ton of buildings off of the boat tour too. We took the elevator all the way to the top floor, grabbed a table overlooking the whole skyline, perfectly in the center, and ordered some drinks. The view was just incredible. Everybody looked really fancy up there, but we just trekked in with our backpacks and walking shoes. If you want to put your feet up, enjoy a cold beer, and take in the sunset breeze, this is the place to go.
CHICAGO SIGHTS
Lincoln Park Zoo:
I wish we had spent more time at the zoo, but we had a pretty packed day. The Lincoln Park Zoo is one of the only free admission zoos in the United States and one of the oldest zoos in North America. For a pretty dense city, this zoo is spread out over a generous 35 acres. There are always events taking place at the zoo, so make sure to check the calendar when you are there. Especially if you go during the holidays!
The Palmer House Hotel:
Have you ever visited a hotel for drinks and fallen in love with it so quickly that you looked up prices to stay that very night? We have. We walked into this absolutely gorgeous hotel, filled with intricate gold designs and luscious carpets. The lighting was dim enough to draw you in, and the leather couches made sure you wouldn’t want to leave. We ordered two cocktails and enjoyed good conversation and people-watching on those amazing sofas. The rooms are comparatively doable if you are interested in staying somewhere unique downtown.
Architecture Boat Tour:
As you may know by now, my husband is an architect. Because of this, anytime we go to a new city, he generally gives me a walking tour of the buildings that surround us. I really appreciate this because it makes me look at cities in a whole new light. Chicago was great for the both of us because we took one of the infamous boat tours throughout the city with a very educated tour guide.
My husband was skeptical of the guide at first, but once she started throwing down the facts and pronouncing architects’ names correctly, he was enamored. The tour was pretty packed and since we didn’t get in line until 10 minutes before it started, we were seated on the top deck of the boat. The only downside was that it was in direct sunlight, so we had to slather on the sunscreen, but there was plenty of shade and breeze during the tour.
Cloud Gate (The Bean):
How can you go to Chicago and not go to The Bean? Sure there were a ton of tourists, but this is something I would definitely not miss. The photo opportunities are fine, but the structure itself is pretty cool. Cloud Gate is the actual name for the stainless steel sculpture, and it is the centerpiece of AT&T Plaza at Millennium Park in the loop community area. This sculpture is made up of 168 stainless steel plates welded together, but it’s highly polished so that the exterior has no visible seams. I’m also a fan of it because it was designed by Indian-born British artist Anish Kapoor!
Walk the City:
The best part about Chicago is how walkable this city is. We spent five hours one day just walking around the city, going in and out of little shops, restaurants, and parks. Besides getting all of your steps in, you get to know the personality of the city by walking around it. I remember we went into an arts and trade fair randomly after taking a 20-minute nap in Grant Park. We loved seeing families and kids running around at the water structures in Millennium Park.
You can walk over to the aquarium, grab yourself a doughnut from Glazed and Infused, or maybe catch a show at Steppenwolf Theatre. And if you can’t walk somewhere because it’s just a little too far or you don’t want to, public transport is pretty darn efficient here as well.
I hope my Chicago, Illinois Sights & Bites guide is helpful for you. The abundance of history, architecture, and eats makes Chicago a fantastic city. If you’ve been to Chicago, what have been your favorite must-sees and must-eats?
Cheers,
