8 Things You NEED to Know Before Visiting Chicago

Photo of a woman looking at the Big Bean from on top of a balcony at Millennium Park in Chicago, Illinois.

Don’t get caught off guard! In this blog, I share eight things you NEED to know before visiting Chicago, Illinois. I also throw in a few tidbits to help you prepare for your next trip based on my Hun and I’s recent 3-day weekend trip to Chicago, Illinois.

1. The Wind is Serious Business

First and foremost, it’s windy. Like, really windy! Rumor has it that the origin of Chicago’s “Windy City” nickname could’ve come from the hot-aired breath of Chicago politicians or, perhaps, because of the cold breezes due to the city’s proximity to water. Why Chicago is named the Windy City is as unclear to me as it is to historians. At the end of the day, the nickname doesn’t matter much to me as what to do about the actual wind.

What you need to know before visiting Chicago: Bring a hair tie, MOISTURIZE your hair, or bring a static removing product. Taking pictures may be a challenge, so try to secure loose clothing and/or jewelry and you’ll survive the strong gusts of frigid wind.

2. Public Transport is AMAZING

Chicago has one of the largest public transport systems in the nation. Not to mention, there are ride share services (Uber, Lyft, etc.), taxis, scooters, and bicycles, too. With so many things to do in Chicago one thing’s for sure – you will have no problem getting around Chicago on a budget!

When my Hun and I walked around the city, we had the opportunity to spot a few unique transportation options. Did you know you can rent a trolley, pedal pub, brew bus, or a party bike taxi – techno-beats included. Oh yeah! Transportation is readily and easily available. Walking is very common in the City and I highly suggest you stroll around town (bring a buddy, for sure) to soak of the vibe. Even more amazing is there are accessible transportation options available, too.

What you need to know before visiting Chicago: Purchase the city’s Ventra card and take public transportation. Not only is it reliable and efficient, but unlimited passes are cheaper than $25 for a few days.

3. Multi-Leveled Streets

Multi-leveled whaaaat, you say? Yeah, a few Chicago streets have two or even three levels to them. What’s even more confusing is the multi-level street could all have the same name. For example, let’s think about the well-known Wacker Drive that runs through the heart of downtown Chicago. Not only is there a Wacker Drive, there’s a “S. Wacker Dr” or “Lower Wacker Dr”.

One thing you need to know before visiting Chicago is there are multiple multi-leveled street names. Lifechicago.com explains it best – When traveling to Chicago, you need to know the “Top” or the “highest level” (aka- “Upper level”) is the name of the main street, which handles most business and commercial fronts. The second level is usually “Lower [insert street name]” and the bottom level can be named the “lower lower” or “service” level. There are stairways to connect all levels. In our Wacker Drive example, “this double-deckered street comprises an upper-level riverfront boulevard and a lower-level roadway for commercial and through traffic, and pedestrian walkway at the water level.”

What you need to know before visiting Chicago: Map your route before you go, pay close attention to street names, then choose your own adventure. Note that once you go underground, your GPS (ie- digital map app) signal will disappear. To combat this, you can either download an offline map of Chicago or follow signage to the nearest street level to re-establish a cell signal to find your way.

4. The Truth About Crime & Safety

Let me be honest – this one caught us a little off guard. Starting from the metra ride from O’Hare airport to the downtown Loop area, we saw cops everywhere. The officers often traveled in groups of two or three and we even saw a group of four on the corner watching activity in an unmarked car!

I’ve heard it said that in Chicago, there is a sharp contrast of wealth AND race, not to mention a history of criminal gang activity. What’s the result? Heightened tension and, sadly, crime, which some say is the reason for the increased police presence. It’s no secret that Chicago was ran by infamous mobster Al Capone and continues to see gang activity to this day.

Let’s Talk About Safety

Even though Chicago was unfairly named the nation’s “Murder Capital”, CBS News released a ranking on the deadliest U.S. cities with Chicago being number 38 out of 62 . Take it as you will, but I don’t give too much credit to the numbers. I say this because the closest cities to where I live – Baltimore, Maryland and Washington, D.C. were ranked numbers 2 and 13 respectively.  To this day, I never had any issues spending time in either city. Anywho, I digress. There were police officers EVERYWHERE in downtown Chicago attempting to keep the streets safe and if you’re not used to it, it can raise a few eyebrows.

On the flip side, some groups feel they are over, and unnecessarily,  policed, albeit targeted. To speak to these concerns, NPR recently released an article referencing decades of police corruption, so who is really keeping who safe? Thankfully we didn’t have any run-ins with the law, witness illegal activity, or experience any threats of violence, but the police presence can certainly be felt on the streets of Chicago.

What you need to know before visiting Chicago: Use the buddy system. Like most large cities, bringing a buddy with you for safety as you move about town is not a bad idea. Following basic safety etiquette, like don’t flash expensive items, observe your surroundings, and watch the news for city happenings before you go, can go a long way towards feeling safe.  

5. This Isn’t Project Runway

Let me be clear- Chicago is NOT the fashion capital of the world. I repeat, Chicago is NOT the place to be for fashion. During our time in the city, we observed the local dress and I would give it an overall rating of “very comfortable”.  Chicago is no NYC, Paris, or Milan, that’s for sure; but it is one top cities for sports in the U.S. This warms my heart because I felt right at home in the relaxed environment of jeans, basic (or sports) tees, and sneakers.

As far as weather is concerned, Chicago sees all four seasons. Plus, the temperature is a bit cooler with a chilly breeze the closer you are to water. Speaking of seasons, here’s what to reasonably expect for weather:

  • Summer: 78°F – 92°F (26°C – 33°C), average rain 3.7 – 4.3 inches;
  • Fall: 70°F – mid-40s°F  (21°-7°C) driest month;
  • Winter: 30 – 38°F (-1°C – 3°C) average snowfall 37” for the year (ie- LAYER UP IT’S COLD);
  • Spring 50s°F (10 – 15°C) to 70°F (21°C).

What you need to know before visiting Chicago: Wear what’s comfortable to you, but dress for the weather and dress for your destination or activity.

6. Shocking Sales Tax

The “Second City” has an incredibly high Sales Tax rate. If you didn’t know any better, you would see a combined state & local sales tax of 10.25% pop up on your next food or souvenir purchase. This tax breaks down to a city tax of 1.25%, county tax of 1.75%, transit authority tax of 1%, and state tax of 6.25%. If you think that’s high, the Hotel Accommodations Tax is 17.4%, comprised of a state occupancy tax of 11.89%, city occupancy tax of 4.5%, and local occupancy tax at 1%. Yikes.

What you need to know before visiting Chicago: By virtue of reading this blog, you have officially been warned. Be prepared to accommodate these taxes in your budget as you consider food, souvenirs, and accommodations.

7. RSVP, Anybody?

We all know the good places book up months in advance. Don’t wing it. Include a healthy food budget for Chicago because there are over 7k restaurants, the most breweries of any metropolitan are in the nation, 20+ Michelin-starred restaurants, and a place to eat for any budget. Know that with reservations come some pretty steep wait times.

Even though some establishments don’t offer reservations, you will have to wait longer than normal at everyday restaurants. Whether getting a Chicago dog, deep-dish pizza, or hot Italian beef sandwich, you may have to wait upwards of 5, 10, 45, or 75+ minutes. Take us for example. I RSVP’d to Michael Jordan’s steakhouse a few weeks in advance of our trip. As soon as I saw an opening, I booked it and within the next two hours the restaurant was fully booked for the next month.

What you need to know before visiting Chicago: Be prepared to wait in line and wait for your food, or not eat at the restaurant at all. Arrive at least 20 minutes before your reservation (or before you want to dine if the restaurant doesn’t take reservations) just to get your name on the list. Be patient, be respectful, have empathy for those in the restaurant industry, and enjoy your delicious meal.

8. Proper Greenspace

The Chicago Park District announced the city ranks among the top five of the Trust for Public Land’s 2021 ParkScore rating, the national gold-standard comparison of park systems across the 100 most populated cities in the United States. I must say, one thing that shocked us was the amount of public parks in the city. About 98% of Chicago’s residents live within a 10-minute walk of a park. How awesome is that! The parks are clean, beautiful, and a welcome respite to the concrete, iron, and glass jungle.

What you need to know before visiting Chicago: Spend time at Millennium Park (big bean), Grant Park (fountain), Lincoln Park (zoo and conservatory), among other gorgeous tree-lined greenspaces.

Those are my 8 things you need to know before visiting Chicago! I hope I was able to provide helpful information, and a little insight, to assist you in planning your next trip to Chicago, Illinois. This is by no means an exhaustive list, so if you have more to add I invite you to drop a comment below.

Antoinette | Frolic & Courage

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