48 Hours in Chicago, Illinois: Best Things to Do and Eat 🏙️

Being one of the most famous cities in the United States, Chicago, Illinois draws visitors from around the world with its iconic skyline, cultural richness, and vibrant atmosphere. Renowned for its architectural marvels and its unique food scene, the city provides plenty to eat, see, and experience throughout the day and late into the night. For the next 48 hours, we'll be getting a little taste of urban sophistication and midwestern charm as we enjoy the best of the windy city. And this is actually both of our first times in Chicago, so we're really excited to see what the city is all about. And fun fact for you, I almost came to Chicago for university. We were comparing between here and Savannah, and I ended up going to Savannah, which is where I met Chad. So thank goodness I didn't come to Chicago. No, I wouldn't be here right now. I know, we wouldn't be here right now. We wouldn't have Chad and Claire. But anyways, we're going to start the day off with some delicious food, so let's head on out. We have made it into Gordano's, which has been around for decades, and they're famous for their deep dish Chicago-style pizzas. And of course, we already put in an order for that, but it takes 45 minutes to make. So we went ahead and got some appetizers just because we are very, very hungry. Got a little Caesar salad and also their soup of the day. But something that I thought was really cute was they call this place Italian-born and Chicago-raised, so it's kind of got a little mix of both. I'm excited to try deep dish pizza for the very first time because I've only seen pictures. I haven't even seen one in real life before. So this is our first time seeing a deep dish pizza in person, and wow, is it deep. Look at that. It's like a lasagna. Wow. I feel like this is the cutest pizza I've ever seen. It's just so thick and full of goodness. Oh my gosh. What's interesting is the toppings look like they're inside of the pizza and not on top. Like on the top, it's just sauce, which is something I've never seen before. It's like a pie, a pizza pie. A lot of cheese. So much cheese. Wow. Wow. Ooey gooey goodness. There's actually less sauce than I thought there would be and more cheese. Yeah, it's a very different experience. It feels a lot more hearty than a normal thin crust pizza and because it can hold so many toppings, it feels more like a healthy meal. You get the proper bite. Yeah, there are a lot of vegetables in there. So this one that we got is called the Chicago Classic and there are onions, green bell peppers, mushrooms, and also pepperoni. Yes, bundle up. It's cold outside. So I ended up having a second slice of pizza, so I am busting full. In order to walk that off, we've decided to come over to Millennium Park to hopefully see the Chicago Bean. I think that's what they call it. Or the Bean, I guess. I can't stop laughing because the Bean is way smaller than what I thought it was going to be. I don't know why, but in pictures, maybe because of the distortion of it, it just looks ginormous and it's just a little jelly bean. But I think it's so cute. I do think it's a really cool art piece because the reflection of the city does make it just seem so extravagant. And even though it's under construction, I'm really glad I finally get to see it in person. So a few first impressions on the city of Chicago. Honestly, it has not been what I expected. The people have been super friendly, the city is beautiful, and yeah, it's just been a lot of fun. Especially during the holiday season, they keep the twinkle lights on all day, so it feels really festive and there are Christmas trees up everywhere. This is a great time of year to visit for sure. Another food that Chicago is known for is donuts, so we went to Fire Cake's Kraft Donut Shop and got two different ones. Oh, I've got to take my gloves off for this. The first one we got is one of their iconic flavors, I guess. It's their pistachio old fashioned, and I think what makes it old fashioned is the shape of it. It's kind of jagged on the ends, it's not the perfect circle. It looks really good, very green indeed. Good donut. It's windy. A windy city. The next one is the German chocolate cake, and I guess a little preview of what's happening tonight. We're going to be going to a German restaurant, so this is kind of like a little appetizer before we, you know, enjoy our German feast. But let's give this a taste. As a chocolate lover, I think I like this one even more. The outside's actually kind of crispy, you know, you can hear the crunch as you eat the donut. So moist on the inside. The inside has some sort of like jam or jelly, so I'm going to try to make it there. You know, it's like a chocolate cake, honestly. That makes sense. More cake than donut. But I see the donut resemblance. So I have to say, this has been one of the coolest tours I've been on, just because she does such a good job at telling you what you want to know, and all the different like architectural styles of the buildings that you're passing, and also like structural marvels. Like, this one building, they apparently could only build on like a certain amount of land, because on both sides it was either the river or this train station. And so they did it, and then they built, and it went over and up. I was like, what? How can people just do that? I think it's really incredible. Yeah, but we highly recommend this tour. We'll link in the description box if you're interested. Even if you're not interested in history or architecture, it's just really cool to be able to get a different perspective of Chicago from the river. For dinner this evening, we've come over to the Burghoff restaurant, and it's been open since 1898. And apparently back then, you could get a beer for just a nickel, and it came with a complimentary sandwich. Of course, those prices are not around anymore, but I did still get a beer because they are known for it, and they're also known for a root beer. So that's what Chan got. Cheers! For our starter, we decided to get the Gretchen's potato pancakes. They're so cute. They actually look nothing like what I expected them to look like, and they smell very smoky. Almost like bacon. Oh yeah. Oh yeah. A little bit sweet, a little savory, a little bit crunchy, and a little bit cozy. Yeah, it has a big jam in it. Ah. So our food just arrived, and I'm looking down at my plate, and I am instantly transported back to Austria. I know this is technically a German place, but you know, they're connected. They're close in proximity, but they have the schpatzel right here, and then the marinated meat. It just looks so good. I love this type of food. And I decided to get the Reuben because Chicago altogether is known for their corned beef. Of course, the Reuben has lots of it in there, and we also have some beautiful house potato chips. This looks so, so tasty. Let's dig in. To continue the German festivities, we will be going to a German Christmas market right here in Chicago. Yeah, it actually first started in 1996, and since then, it has been welcoming a lot of people from around the world, and apparently it was created to encourage trade with Germany. So I'm really excited to see a lot of like the German goods. You can buy some gifts, so we'll be on the lookout. Yeah, this is also our first Christmas market together, so I can't wait to see what kind of goodies they're selling, and maybe we'll pick up some festive ornaments for a treat. One thing I wanted to add is apparently my heritage is from Germany, so my great-grandfather came over. I was talking to my grandma once, and she said that when she was a kid, her parents would be speaking in German when they needed adult conversation. So I guess when they were fighting or whatever. Yeah, same thing with my parents. They would speak in Taiwanese. $13 please. So we have scoured the We have picked up our hot chocolate along with a souvenir mug, which we both think is extremely cute. I love that because honestly, you could even hang this up on the Christmas tree as like its own ornament, but let's give it a try. Good whipped cream. Oh, good hot chocolate. Wow, that is so rich. I've been so excited for this just walking around. There's so many vendors that sell it. All right, your turn, Claire. Especially good when it's so cold outside. So everything here is pretty much cash only. So we did bring cash from home, and it's fun to hold cash in your hand. I feel like no one really takes cash anymore. It's actually typically credit card only. So it's fun to, you know, hand over the wad of cash, get some change in return. Yeah, so vintage. Yeah, it feels like old times. That hot chocolate did not last long. It has been a frigid day, and we slurped that hot chocolate down like there's no tomorrow. I think we're actually going to end the video here for now, just because we're going to come back to the hotel and cozy up. But this was just a little taste of the Christmas market. We're going to come back tomorrow night and feast up on some more German goodies. But with all that said, night night. Good morning from day two in Chicago. We are making our way to a very iconic restaurant chain that serves beef sandwiches and hot dogs. I'm so excited. We've been waiting to get these delicious hot dogs in our mouth. And I was looking at the pictures. They look very unique. Definitely a hot dog I've never had before. It was so cool to stand up there and wait for our order because you can see all of the workers multitasking. They're all working together to pump out these Italian beef sandwiches and hot dogs. And it was really cool to just see them in action. Very interesting. My goodness. So first walking into this place, I can immediately feel like the heritage that Portillo's has in the city of Chicago, because they have all these like antiques like up behind me is this original banner from 1938 of the Stanley Cup. And I just thought it was really cool that they have that piece of history right up there front and center. And it kind of gets you ready to eat and taste a piece of Chicago. So right here we have the Italian beef sandwich and some peppers right on top. Huge peppers. It's like a soft, tender beef sandwich with all the juices and the peppers. It has like a tiny bit of a kick. Not much, but like the perfect amount. So next up is the Portillo's beef hot dog. Pretty classic. It has pickle, peppers, tomato, and then this like sesame. Oh, it's a poppy seed bun apparently. All right, let's go to try. I like the pickle and the tomato on there. It takes it down a very different path. It's like fresher, like a garden. I got a big chunk of that banana pepper and the pickle, so a lot of sour flavors coming through. But I do agree with Chad, it does feel like you're eating something a lot fresher. It has that bit of, you know, kind of like the garden vibes that Chad was talking about. The garden dog. If you go back for seconds, you know it's pretty good. I went back for another hot dog because I couldn't get enough of it. And actually something I forgot to mention is we ordered it without the celery salt because we were recommended to do that. Apparently with it, it's a little bit too salty, so I don't know. I thought it tasted pretty good without it. What else did we get? We also got the Portillo's chocolate cake, which is another classic. It looks very, very moist, almost like that cake we had in Paris. This is the most moist. Is it most moist or moistest? Both of them sound wrong, but man, look at it glisten. Cheers. Oh, that's a good chocolate cake. Delightful. Truly delightful. We have made it over to Maggie Daly Park and I actually signed us up for some ice skating this afternoon. We are so full of hot dog right now, but I think the exercise will be good for us. It'll help us digest. And also what's really cool about this ice skating rink is that it's a ribbon and it goes all throughout the park. And so I've never ice skated on like a pathway before, so I think it'll be really fun. Oh, I can see the path now. It's pretty cool. There's the path. I gotta say, ice skating is so much fun because sometimes when you're going on that downhill, you don't even have to do much effort and you're just flying basically. We just finished our first lap around the rink and it is so cool. But one thing I've never experienced before is like a downhill or an uphill on the ice, just because anything we've ever been on is like a lake, which is completely flat. That's right. But like, it's pretty exciting. Yeah, we were like using our muscles extra hard going up the hill and then when you go downhill, you get, you know, you start to get faster. Yeah. And I get nervous, but this is really fun. It's a really cool concept. Yeah, I love it. And the city behind us, like it's just amazing. So Chad completely surprised me. He brought me up to Cindy's Rooftop, which is actually mentioned by our hotel when we were checking in. And I am blown away by this view. You can see the bean where we were just ice skating, another ice skating rink, and also Lake Michigan all the way out in the distance. So this is such a beautiful spot. We've come at sunset so we can watch the lights of the city start to glow as the sun sets. So I got the tree hugger. And then here I have an old fashioned and I was looking up online that apparently the old fashioned came from Chicago. I haven't verified that. But I thought I'd try it in honor of that fact. The possible fact. Yeah, the possible fact. It's like you're drinking a forest. bratwurst or some sort of food, some dinner and then hot chocolate and maybe a German beer. We'll see. It's definitely a very busy Christmas market tonight. But we got a bratwurst with sauerkraut and I put some mustard on the top and then we also got a dark beer to share. It's really cute. Like it's small. Yeah, it's miniature. Goodbye. I'm such a fan of sauerkraut and mustard and sausage. I don't even know how you fit this whole thing in your mouth. Go for this part and then get the bite. Get the bread after. No, that's the opposite. Yeah, go for that. Exactly. Kind of. Yeah, yeah, you got it. So next up we got some lentil soup. It is perfectly hot and just delicious. I love it. I just want to eat lentil soup in the forest all the time or in the city. I feel like this Christmas market is just getting me so excited for when we go to Europe and experience the real Christmas markets there. It's gonna be a fun time. I know it. So we just went to get a Bavarian pretzel and I haven't used cash in a long time and I gave him 25 cents short and Chad told him like she's trying to trip you and I'm like no, oh my god. I gave him extra quarter but oh so embarrassing. Very good pretzel. Thank you. The Christmas market food tour continues on and we have pierogies now. I think that's how you pronounce it but we got them filled with beef and we got all the toppings so we have sour cream, bacon, and onion. I don't know if that's traditionally how it's supposed to be eaten but it sounded pretty good so we got it all. Dense dumpling. Oh wow. All right. It won't stop us. This is something that I would get multiples of. I think it's really good. Yeah. You like it? I do like it. Oh wow. Don't judge me. Don't judge me. What's next? What's next? I feel like we just keep eating and eating handing over cash. All right. Next up is strudel. What do you think? I'm embarrassed by my zip lock bag. They are all really good. I like the cherry. So we went and got a cherry strudel along with a hot chocolate. Yep. Cheers. Cheers. That's a great strudel. Flaky on the outside, gooey goodness on the inside. Oh yeah. Yeah. Wow. It's so pretty. Yeah. A little bit tart as well. I mean after making strudel in Austria, oh I just appreciate it even more. It's like the type of strudel that while you're eating it you just know like if I died in this moment, I'd be all right. We know what Chad wants to be buried in the grave with. This strudel. We decided to get another Bavarian pretzel because the first one was so good and this time we got it with mustard so we're doing it right. And then also we got some cappuccino nuts that we smelled like was wafting around in the air. Smells so good. We tasted them. Chad got a little bit of that and I think we're going to end the video here because we are pretty much filled up and we're going to go and snooze the night away. But thank you so much for joining us here in Chicago. If you want to watch us travel to 50 countries around the world, hit subscribe. With all that said, we'll catch you on the next one. Bye!