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Weekend City Guide to Chicago, IL

Chicago is one of the most fun cities I’ve been to. I mean, where else can I go and have a gourmet all-you-can-eat buffet with bottomless mimosas in a day club at noon on a Saturday? I fell in love with Chicago so quickly and I can’t wait for my next visit. Here’s what I did, wanted to do, and plan to do next time I’m in the windy city (which btw gets cold at the drop of the hat so be smarter than me and ALWAYS bring a coat).

Where To Stay

Moxy Chicago Downtown

This is one of the coolest hotels I’ve ever stayed in. I mean, the room we stayed in had oversized bunk beds. It also has a super lively bar downstairs with amazing drinks, and a taco shop too! It’s in a prime location, a quick Uber ride to everywhere you want to go.

Chicago Athletic Association

This is such a chic, luxurious hotel. It has multiple restaurants, a game room, a bar, and more! Even if you don’t stay there, you should still go check it out! There are plenty of photo opps and experiences to take advantage of while you’re in town.

Hotel EMC2

This is a super fancy, hip hotel in a prime location in Chicago. It has The Albert, an amazing restaurant, as well as other shops and cafes. I love how chic this place is! I HAVE to check it out one day soon.

Where To Eat In Chicago


Honestly, any time I go to a city with an Eataly, I’m going there. They have the best pasta dishes in existence, amazing Italian food shopping, and endless restaurant options. The place is basically a market for all things Italian. There’s a pizza place, gelato spot, a sit-down restaurant or two, bars, and of course shops where you can find everything from authentic ingredients to kitchen tools! I went to my first one in New York and have been obsessed ever since. I’m super excited because we’re getting on here in Dallas soon and I can’t WAIT!


If you’re craving something sweet and are low on energy, get over to Bombobar for your fix! They have these insane shakes that almost taste as good as they look. I say almost because the sweets on top are okayyyy but the shakes are SO good. They also do these huge stuffed donuts, gelato sandwiches, and hotter chocolates (that are kind of like the hot version of the shakes.)

Garrett’s Popcorn Shop

Honestly, if it doesn’t come from Garrett’s, I don’t want popcorn anymore. It was SO dang good. The caramel was great – but the cheddar STOLE THE SHOW! Its literally like eating fresh cheese on popcorn (it might actually be that but who knows). The lines are long, but trust me when I say they’re worth it!

Lou Malnati’s Pizzeria

If you HAVE to have some Chicago pizza while you’re in town, I suggest going to Lou Malnati’s. The place is packed with super long waits, so you know it must be good. I ended up ordering to go and still had to wait over an hour. It is my understanding that it is some of the best Chicago pizza in the city. That being said… I can now confirm that I do not like Chicago pizza. I KNOW! Don’t hate me. I’ve had it many places but figured if I tried it in actual Chi-town at the best place that serves it then I would be in love. While I can admit that I love the toppings on the pizza, I just can’t get behind that sour deep crust. It’s not my jam…not even with ranch (I tried).

Velvet Taco

If you live in Dallas, just skip this part. I know you’re rolling your eyes at me right now because we have Velvet Tacos everywhere. But if you’re NOT from DFW, you’re going to LOVE Velvet Taco and they have one right in Chi-town. It’s kind of an Indian-inspired taco spot with all types of different tacos from Spicy Tikka Chicken to Shrimp and Grits! Whatever you choose (and you can’t go wrong) make sure you get some Red Curry Coconut Queso and the best red velvet you’ve had in your life! You can thank me later.


I’m going to talk more about this place in “nightlife” section, but if you’re into brunch, parties, and bottomless drinks, this is your place!

Portillo’s Hot Dogs

If I have one regret about my trip to Chicago, it’s not going to Portillo’s more often. Unlike the Chicago pizza, I surprisingly LOVED my Chicago dog! I’ve had them at other places (cough cough *SONIC* cough cough) and was not impressed. But this real, authentic, delicious freaking hot dog was SO FREAKING GOOD I would easily go back to Chicago just to get 10 more. This is another one you should NOT leave The Windy City without trying.

Urban Belly

I originally ran into Urban Belly because after a day of drinking and walking round, I had to pee LMFAO. But they make you buy something to use the restroom, so I figured what the heck. Turns out, they have dumplings and more. If you know me, you know dumplings are one of my favorite foods so I was happy to oblige. Let me tell you those dumplings were THE BOMB. I scarfed them down so fast. Plus they were super cheap, which is honestly pretty normal for most places I’ve been.

Things To Do In Chicago

Walk The River

One of my favorite things when I go to new cities is to just walk around. You’ll always discover parts of the city you otherwise wouldn’t. Chicago is no different, except for that they have a huge, beautiful river running plum through the middle of it. It’s lined with hotels, restaurants, and businesses so you’ll really see if all.

Go To The Bean – It Might Surprise You

I was shocked to learn that The Bean wasn’t surrounded by skyscrapers! But it’s actually in Millennium Park in Chicago. When we were there, there was a huge food festival going on just behind it! Of course there were tons of people, so I must suggest that if you want to avoid the crowds maybe try going early in the morning.

No. 18 Karaoke

My friend Jessica recommended this place to me. And while I couldn’t make it there on my trip, I’m definitely adding it to my list for next time! From what I hear you can rent a private room for $30 an hour and sing your heart out! (Check out Jessica’s Chicago Travel Series to see what else she recommends you do while you’re in town!)

Go To The Navy Pier

It’s way more than just a Ferris wheel – although you’ll want to see that too. There are a few rides and great views of the lake and the city. It was one of my favorite places to snap some pics while I was there. More than anything, it has what I can only describe as a food mall underneath. It’s a fun spot to walk through and people watch. Just make sure you stop by Garrett’s Popcorn Shop and get some cheese popcorn before you leave. Actually, if you don’t do that before you leave Chicago you’re missing out. Best popcorn I’ve ever had in my LIFE.

Nightlife In Chicago

The Violet Hour (a secret bar!)

One of my Instagram friends, Kerrie (@foodsparks), told me about this gem! According to her, there’s a graffiti wall on a building, and you can’t see the door unless you look reallllly close for the handle. She said there will be random people standing in a line on a sidewalk, but that’s where this speakeasy is! She said she loves it because it’s beautiful inside with marble and velvet notes. I HAVE to check it out next time. Also…good luck finding any pics of it online because apparently NO cell phone usage is allowed inside. I mean…clearly I HAVE to go now.

Moxy Chicago Downtown

Moxy is actually a hotel in Chicago, which I’ll get to later. Right now, let’s talk about the bar at this place! It’s everything a hotel bar should be. Super lively (and by that I mean tons of people but not too many), fun games, delicious drinks, cool neon colors and most importantly, great music! I was pretty stoked to have this bar in our hotel. So much so that we finished up there both nights that we were in town.


Okay, technically this is a day party but BRUH! You do not want to miss it. When I asked my Insta-friends where to go while in Chicago, an overwhelming number of them told me to head to Fremont for brunch on a Saturday. It was EVERYTHING! Amazing brunch with everything from a fresh oysters and shrimp to pizza and Mexican food. All in what is essentially a two-level club with dj’s, multiple bars, and BOTTOMLESS DRINKS! As if the food wasn’t enough, right? I could go on and on all day about why I loved this place but I’m trying to keep this brief so just do yourself a favor and GO.

Three Dots and a Dash

One of my supafly friends on the gram recommended this place to me! Its essentially the coolest tiki bar in the city. I mean, just click play on that video up there!

So, would I revisit to Chicago?

I dont think Ive ever travelled to a place that surprised me as much as Chicago does. It was such a beautiful city, from the architecture to the nature aspects. I fell in love with The Windy City so quickly and look forward to the next time I can go back and do all of the things!

Have you ever been to Chicago? Did I leave some places off of this list? Sound off in the comments below! Or better yet, tag me in your favorite Chicago spots on Instagram – my handle is @gingermarieblog.I cant WAIT to go back and explore even more.