Chicago – Best Things To Do for First Timers

Welcome to The Windy City!

What’s up guys!

It’s Brendan and I wanted to share with you my trip to the one and only, Chicago! I’ve been to the city twice before and it remains on the top of my list of favorite places to visit. My family and I decided to go last minute for a quick 48 hour trip and like always, it didn’t disappoint. There are so many incredible places to see and of course, amazing opportunities to get great photos for the gram! I want to share some of the Best Things to do in Chicago.

What I love about The Windy City is that it’s like New York but way more relaxed and CLEAN. Chicago takes pride in how clean they keep their city and I don’t blame them. It makes for great picture taking. The architecture of the buildings is inspiring, it even had my brother inspired to go to school for architectural design. They’re very modern and pleasing to the eye, with skyscrapers lining every street. Everywhere you go is picture-esque, I couldn’t put my camera away!!

The city is so well designed, with intricate roads and highway weaving in and out of each other that minimize traffic and makes getting around extremely easy. And don’t even get me started on the townhouses here!! They are exactly what I see myself living in. Hopefully one day I’ll have my own! Every time I visit, I fall more and more in love with this city. It has the perfect balance between city and nature.

Chicago has everything there is to do and definitely deserves more than a two-day stay. But with that being said here is my 48-hour, jam-packed adventure into the Windy City!

Where to Stay

~ Loews Hotel Chicago ~

We had the pleasure of staying at the luxurious Loews Chicago Hotel, which offers great views of the city and Lake Michigan. We began our first day, bright and early with some free room service. Who can resist that?! We ordered the donut French toast (yes, DONUT) with blueberries and freshly cut apples. It tastes just as good as it sounds. Of course, we had to have their gourmet pancakes and followed that off with the banana coconut smoothie which was to-die for. What a great way to begin the day!

Things to do in Chicago

~ Big Bus Tour ~

For first timers, especially for those who don’t have a rental car, the Big Bus Tour is really convenient if you’re looking to hit up all the popular sites. They have stops all throughout the city and you can hop on and off whenever you’d like. We bought a one day pass for only $36 and spent the entire day site seeing, coming and going as we please. Such a great deal! You’d spend twice as much taking an uber around.

If you sit on the second level of the bus, you get to see the city from the comfort of your seat. It was so nice to just sit there and take everything in.  They even have great guides who know a lot about the history of Chicago. Don’t worry about waiting too long for a bus, they have so many of them so you don’t have to wait more than 10 mins at a stop which is really nice.

Here’s there’s website for more info: Big Bus Tour.

~ Giordano’s: Chicago’s Original Deep Dish Pizza ~

For all you foodies out there, Giordano’s Pizzeria is a MUST! You can’t go to Chicago and not pleasure yourself with the original deep-dish pizza. We went around lunchtime and surprisingly, it wasn’t too busy. However, we had to wait a whopping 45 mins for our small deep-dish to cook. It’s the price you pay for delicious and authentic deep dish pizza! The Classic Giordano is an easy go to for a great price. It has pepperoni, mushroom, green pepper, and onions. It’s cheesy, thick, and crunchy all at once. It’s perfect for first-timers like us and the small size was able to feed three of us with plenty to spare.

Deep dish pizza at giordan's in Chicago

Unfortunately when we went, the lighting was just too dark to get great pictures of the pizza. However, here’s their website to get a good sense of what deep dish is all about: Giordano’s.

~ Navy Pier ~

Once, we were done gorging ourselves with great pizza, we hopped back on the bus and headed to the Navy Pier. The Pier is a great place to enjoy views of the lake and has tons of cool spots to take some pics. Before getting to the main area of the pier, we first strolled through the Crystal Gardens. It’s free to enter and is really cool to see. Last time we were here, it was closed down so I was very excited to finally see what was inside. It feels like you’re walking through the greenhouse at Hogwarts!!

The Crystal Gardens lead right into the main area of the pier which has perfect views of the skyline of Chicago. The buildings tower to incredible heights and seeing them from afar is definitely a sight to see. The pier also has a newly built ferris wheel and carnival area with some rides for the kiddos. I love coming here to look at all the sailboats cruising in the lake off in the distance. They also offer boat tours that take you out into the water for even better views of the city from afar. Make sure to bring a jacket! The lake winds can be ruthless.

~ Millennium Park ~

My favorite part of the tour is the staple of Chicago, The Bean, also known as the Cloud Gate. It’s a dope sculpture that looks like a giant metallic jellybean, hence the name. It’s like an interactive piece that feels like it’s always moving. The reflectiveness of the sculpture warps the view of the buildings and trees surrounding it, making for some neat photos. I got really lucky because right as I got there, it started to downpour. So everyone took shelter underneath the sculpture, clearing out the entire area on the side for an amazing photo opp! The crowds can get pretty large, but hey, I don’t mind playing in the rain for a great pic!

After exploring the bean, the rest of Millennium Park has so many areas to check out. Buckingham Fountain, Columns, etc. And it’s even more beautiful at night, so definitely take a walk over there in the evening too if you can!

~ Ramen-san ~

raw tuna sesame crisps and shio ramen at ramen san in chicago

Our last night in Chicago we sought out my family’s favorite dish: RAMEN. If you don’t know already, I’m part Japanese and always on the hunt for great ramen shops. And boy did we find some GOOD ramen in Chicago! On Hubbard street sits Ramen-san and if you like noodles or Japanese food in general (OR BOTH) you gotta stop by this place. It’s hard for me to finish an entire bowl of ramen, soup and all, but I slurped up every bit of the Shio ramen bowl. The Shio ramen consists of chicken broth, a molten egg, tofu, and nori. YUM!!!!! We also started off with raw tuna on sesame crisps with poblano and avocado which was super delicious.

Long story short, I’ll definitely be coming back here next time I’m in the area! You can find their menu and instagram on their website here.

There you have it folks!

For all you first time Chicago goers, I hope this gives you some inspiration for the best things to do while visiting! Hopefully next time I’ll be able to stay longer and venture out into some more awesome areas. Til next time!

Thanks for reading!



  1. Caitlin Johnson
    August 13, 2017 / 2:25 pm

    I might be going to Chicago next summer for a family reunion. I hope I get a chance to visit all these cool places.

  2. Melanie Hill
    August 20, 2017 / 8:41 am

    I’ve never been to America but your description was so tantalising I really want to visit Chicago😊

    • themillennialaffair
      August 27, 2017 / 1:44 pm

      So glad this post gotyou inspired!!!

Leave a Reply