Chicago for First-Timers

Going to one of the best cities in the world?! Well, I got some pretty great recommendations for you first timers. I am lucky enough to call this beautiful city my home and I can honestly say it is one of the best cities in the world. There is an endless amount of things to see and do, so you will never be bored. It is a lively and vibrant city that doesn’t sleep. Each season offers plenty to do, but I always recommend visiting in the summer since there is nothing better than a Chicago summer.


Chicago Musts for First-Timers:

The Bean and Millennium Park – this is a classic, and you most likely have seen pictures of the bean. It is a cool place to walk around and hang out at for a bit. Millennium Park also has live music and movies in the summer that you can enjoy for free. In the winter, they have an ice rink that you can check out too, just make sure to dress warm :).

Wrigley Field – home of the Chicago Cubs who won the world series after a century of being cursed. Now, this stadium is not only iconic to see but there are a ton of bars and restaurants in the area that are so much fun to go to especially on game day.

Lake Front/Beach – the lake front is so beautiful at any time of the year but if you are lucky enough to make it in the warmer months, then check out the beach for a fun day in the sun. You can also, walk, run, or bike the many miles of lake front path. There are also restaurants along the way, where you can get some food and refreshments (mostly open during the summer).

Michigan Avenue/Magnificent Mile – I love Michigan Avenue the most in the winter when it is all decorated for the holidays and it just fills my heart with joy. But during the summer months, you will find it filled with street performers and tons of people walking around. This iconic street is filled with endless shopping and restaurants so you will find plenty to explore.

River Walk – in the winter you will find snow globes you can grab some drinks in and keep warm. In the summer months you can sit outside, sip some wine and watch the boats go by. There are also plenty of restaurants along the way with some pretty views of the river as well.

Restaurant Row (West Loop) – west loop is a town in Chicago filled with tons of amazing restaurants and bars. Make sure to check out the iconic Girl and the Goat, but make reservations well in advance.

Check out some of my favorite restaurants in Chicago here!

Navy Pier – this is where you will find the huge Ferris Wheel that has some spectacular views. The pier is filled with shops, entertainment, and lots of restaurants. It is also home of the new, biggest rooftop in the world called Offshore. If you really want to get fancy, then you can even enjoy a nice meal as you cruise on a boat and get a skyline view of the city.

Deep Dish Pizza – you cannot visit Chicago and not try deep dish pizza. So make sure that you make it at least one of your meals while in town. Some famous spots include: Lou Malnatis, Gino’s East, Pequods, Giordanos, and Pizzeria Uno.

Lincoln Park/Zoo – the best part about the zoo is that it is free and Lincoln Park is super pretty in general. In the winter, you can come see the zoo decorated in many, many lights and even watch the light show. The summer months are the most busy, since most of the animals are outside enjoying the heat. The zoo always has events going on, so whichever season, you will find it to be a good time.

Sears Tower/Willis Tower – formerly Sears tower (which is what all Chicagoans still call it); now called Willis Tower contains the famous skydeck. Although it is super cool, it is not for the faint of heart because you are literally standing on glass from the 103rd floor. The wait times can be super long and out the door sometimes, so plan accordingly.

Catch a Sports Game – Chicago has some of the best and most loyal fans. I mean we waited over a century to have the Cubs finally win the World Series, and we housed the one and only Michael Jordan. Depending on the season and how much time you have; I highly recommend experiencing a sporting event. My favorites are definitely the Chicago Blackhawks games because the atmosphere is unreal.

Nightlife – there is no shortage of nightlife in this city. Clubs, dive bars, outdoor bars, underground bars, pubs, sports bars, jazz bars, bars with cool drinks, bars with live bands, bars with djs, day party bars, weekday hot spots, LGBTQ bars; you name it, Chicago probably has it. Different neighborhoods have different types of scenes as well, so it really just depends on what you are in the mood for but you will have endless places to choose from.


Since, I am a local this is definitely not the last post on Chicago. I hope to be writing so much more on this amazing city especially as I discover more of it.

Happy Travels – xoxo Dre ❤

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Just a girl living out her dreams of traveling the world.

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