Visiting Chicago Like A Local – Sweet Home Chicago

Having a local guide helps you really explore a country/city to its fullest and so, no travel blogger could fully call themselves a travel expert if they can’t do this in their own city. Consider This My Ultimate Guide For Visiting Chicago Like A Local!!!

A question EVERY traveler will ask each other is, “Where are you from?”.

It’s a simple question but when you’re on a sabbatical with no exact plan of when or if you will return “home”, you start feeling like you have to add to your response. A simple question becomes so complex; you start questioning what is “home”?, where is it?, is it the last place you permanently lived at? where you were born? or do you go the cheeky route and say something like, “Well today, this is home.”

I decide that these strangers asking me this simple question required a disclaimer,

“Well I’m from Chicago but haven’t lived there since I started traveling x months ago. And did I mention I’m Guatemalan too?”

Being a traveling nomad is G R E A T…BUT having a place you call “home” makes you appreciate not only your travels but your “home” city even more.

Visiting Chicago Like A Local – Plan Your Visit






Best Time To Visit Chicago

Visiting Chicago Like A Local - Promontory Point

The best time to visit Chicago is during the time locals call, “Summer Time Chi“. “Summer Time Chi” happens during June – Mid September when Chicago has the best weather. If you travel to Chicago during this time, you can guarantee you will get the best taste of what the city has to offer. Join in and do as the locals do by filling your days with tons of activities.

Getting Around Chicago

Visiting Chicago Like A Local - Navy Pier

Moving around in Chicago is very easy. Public transportation is a common way of getting around especially if you are visiting Chicago like a local and also economical too.

Trains / Bus

Chicago’s train system is very well organized and able to get you to all tourist and local spots. When you arrive, ensure you pick up a Ventra Card (Available for purchase at all train stop kiosks and refillable for all your train and bus travels in the city.)

Just ensure you check the schedule for operating times as only the “Blue Line” runs 24 hours and many others stop operating at 1:00 am then resume operation anywhere between 4:00 am – 5:00 am depending on line.

If the train can’t get you to your location, buses can certainly get you there. You can use your Ventra card to pay for both bus and train rides.

Learn more about using public transportation in Chicago by visiting the Chicago Transit Authority website here.


Uber is available in Chicago. If you have a bigger party this may also be cheaper than using public transportation. I always price out even as a local. 


Have more in your party and want to venture outside of Chicago? Consider renting a car. Drivers in Chicago for the most part are easy to share the roads compared to drivers in other cities in the US.

Find your sweet wheels HERE.


English is the predominant language in Chicago but visiting Chicago like a local, don’t be surprised if you find yourself exploring neighborhoods where Spanish may be the first thing you hear. (Like Little Village, Pilsen and Humboldt Park)

Additionally, the second biggest Polish population after Poland is Chicago? So if you are in neighborhoods near Midway Airport, Portage Park or Belmont Craigin, you can guarantee you’ll hear Polish as well.

Where To Stay In Chicago

Radisson Blu Aqua Hotel Chicago


  • Chicago Athletic Association – A great hotel if you are looking to be morphed into time as this hotel has a very 1920’s feel.
  • Radisson Blu Aqua Hotel Chicago – This beautiful modern hotel has all the amenities one could ask for including a gym, indoor/outdoor pool, bar, sauna and steam room. I had a stay-cation here and was left wanting to extent my holiday.


Great neighborhoods to consider staying when visiting Chicago like a local:

  • Chicago Loop – Right the action and close to all major city attractions
  • Pilsen – One of my fav places, filled with art, culture and character.
  • Wicker Park – Hipster neighborhood offering a wide range of restaurants and shops
  • Lincoln Park – Upscale, close to the lake and not far from the city center.
  • Logan Square – A bit outside of the city, (But connected well with public transportation) this is a cool place to experience lots of great bars, eateries and mom & pop businesses.
  • Fulton Market – Where creatives and young professionals hang out.

Must Do While Visiting Chicago Like A Local

Bicycle Ride – Cruise on the south side part of the lake toward Promontory Point for great skyline views.

Baseball Game

  • Sox Stadium is perfect if you want to take in some tailgate action outside of the stadium before the game.
  • Wriggly Field gives you a taste of old school baseball seeing the legendary Cubs play. Don’t forget to get into the action with a pregame in the many bars around the stadium.  

Pilsen neighborhood – Take a stroll during the day for some fabulous street art by Chicago favorites.

Second City – The place to go for a comedy show when visiting Chicago Like A Local. Legends like Tina Fey, Chris Farley, Mike Meyers and Amy Poehler have studied here.

Chicago River Walk – If you get lucky, catch the bridges separate to let ships through the river. Want to really immerse yourself into Lake Michigan? These are some of my favorite ways to enjoy the lake and river in Chicago.

Bahía Temple – Outside of the city and don’t forget to pack a picnic to enjoy along the lake. (If you have time be sure to visit the “Home Alone” movie house which isn’t far away.)

North Avenue Beach – Lively place to catch some sun and enjoy the lake despite it being called “Beach”.

Must Visit While Visiting Chicago Like A Local

Visiting Chicago Like A Local

As a world traveler, I can confidently say that there are plenty of tourist-worthy attractions in the Windy City. Even a local like myself can’t get enough of them.

To help you plan your trip and explore the best tourist attractions that Chicago has to offer, be sure to check out my guide of the top Tourist worthy attractions in Chicago. This guide will provide you with all the information you need to make the most of your visit and explore the city like a local!

Where & What To Eat

Visiting Chicago Like A Local - Deep Dish Pizza

From Chicago style, to the iconic deep dish pizza, my Chicago eats for tourists by locals food guide has you covered. You will find the best local recommended places to eat at, includes what dishes to choose and offers tours to give yourself and your taste buds the best city experience.

Where To Party

I’m partial to a bit of drinks and parties both at home and while I travel. Lucky for me, I’ve traveled, I’ve partied and gathered a bit of expertise on the industry and what tourists look for. Chicago nightlife offers something for everyone and will not disappoint a tourist also partial to a good night out.

The key is knowing where to go for what you want. This travel guide to nightlife in Chicago will have you where you want to spend the night in this city. From cocktail, local gems, live music and where to dance, I have you covered. I’m an expert after all.

Where Else To Visit Near Chicago

Exploring cities near Chicago can be a fun and adventurous way to spend a vacation. With short flights and car trips, you can maximize your time and see more than you thought possible.

See the places I, (a travel blogger), think are worth checking out as they are easy to explore from Chicago using my Easy Trips From Chicago ideation guide.

Cheap flights with cashback

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