The author Lea Rose Allbaugh admiring the skyline of Chicago, Illinois

20 Chicago Travel Tips & Things to Know in 2023 (By a Local)

From visiting Chicago for the first time to becoming a local myself, there are tons of Chicago travel tips I wish I’d known sooner. For example, don’t make the mistake of trying to visit all the attractions in one day, and note that some major museums are closed on Mondays. 

With these and more local insights, I’ll save you the hassle and make visiting Chicago a breeze. It is the Windy City, after all!  

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20 Travel Tips for Chicago

Don’t try to hit up every attraction in one day

The author's hand and The Bean from afar
The Bean!

Chicago is chock full of fun attractions. From Cloud Gate in Millennium Park to Lincoln Park Zoo, the foodie scene in the West Loop area, and everything in between, Chicago’s got it all. As eager as you may be to hit up everything in one day, it’s just not possible or realistic to do so. 

Instead, plan things strategically based on time of day and where attractions are located in the city. If that sounds like a headache, we’ve got you covered with a 5-Day Chicago itinerary.

Take public transportation

The elevated "L" train passing by Chicago
The elevated “L” trains run through the city

The Windy City has one of the best public transportation systems in the country and I highly recommend that visitors take advantage of it. The Chicago Transit Authority (also known as “the CTA”) operates buses and the elevated or “L” trains which run throughout the city. 

Public transportation is affordable, reliable, and great for getting around Chicago. You can purchase a CTA card at any train station and most convenience stores. 

Try some classic Chicago foods, but it’s also okay if you don’t

Crostini and drinks on a table in bar avec in River North
Crostini from bar avec in River North

This may come as a controversial hot take, but don’t feel like you have to try all the Chicago staples like deep dish pizza or a Chicago-style hot dog. If you’re interested, definitely give it a go. Places like Pequod’s Pizza and Lou Malnati’s are great options for deep dish pizza, and Portillo’s for hot dogs. 

However, Chicago is full of so many incredible restaurants with every cuisine imaginable, so don’t feel like you have to limit yourself!

Wear good walking shoes

The author's shoes making an illusion of stepping the buildings on the city

Throughout the year, you’ll find that Chicagoans wear sneakers just about everywhere. When you visit Chicago, I recommend that you hop on board, too. Whether you’re exploring the Magnificent Mile, Millennium Park, or museums, you’ll want a pair of comfortable walking shoes.

Weed is legal

One of the Cannabis Dispensaries in Chicago
(photo: Jonathan Weiss / Shutterstock)

As of 2020, Illinois is one of the states where weed is recreationally legal. This means that in Chicago, anyone ages 21 and over can purchase weed and weed products. There are a variety of dispensary stores throughout the city. 

If you plan on partaking, just be sure you’re purchasing from a licensed seller and always adhere to the law. For example, don’t smoke in public places, while driving, on school grounds, etc.

Locals are friendly

Locals from Chicago crossing a street
(photo: Lissandra Melo / Shutterstock)

One of the reasons why Chicago is so great is the people! Midwestern hospitality is alive and thriving in the Windy City. So, if you ever have any questions or need help during your stay, it’s okay to go ahead and ask a stranger!

Many places are closed on Mondays

View of one of the exhibits inside the Museum of Contemporary Art
An exhibit at the Museum of Contemporary Art

If Monday is one of the days you’ll be in Chicago, be sure to check the hours of any attractions and places you plan on visiting. Though not all, many places like the Art Institute of Chicago, Museum of Contemporary Art Chicago, and Chicago History Museum close on Mondays. The same applies to many small businesses. To avoid hassle and disappointment, plan ahead! 

Check Covid mandates before you visit Chicago

The Lions outside the Art Institute wearing a mask
The lions outside the Art Institute wearing masks (photo: Kevin Kipper / Shutterstock)

Depending on the state of the pandemic, Covid mandates may or may not be in place in the city of Chicago. At times, mask mandates and proof of vaccination may be required for entry to certain or all businesses. Before your visit, be sure to check if there are any mandates in place, and then travel and pack accordingly. 

Always make reservations

The author looking at the menu on the rooftop of bar avec
Views from the rooftop at bar avec

It’s typical that for most Chicago restaurants, a reservation is required, or at least highly encouraged. Of course, this isn’t the case for more casual joints, but if you plan on having a sit-down dinner anywhere, it’s a good idea to make reservations in advance. 

Popular restaurants in the West Loop and along the Chicago River get especially booked up. And if you plan on visiting a riverside restaurant in the summer, there may be an additional patio fee.

Don’t underestimate the weather

The author posing for a photo with a colorful sky on her background
Chicago in February is still cold and snowy!

From the frigid temperatures of winter to the blistering heat in summer, Chicago really hits each end of the spectrum when it comes to weather. Before visiting, check the weather and pack appropriately. Packing layers is always a good idea!

Don’t be afraid to leave downtown and explore other neighborhoods

View of people and buildings in the neighborhood of Lincoln Park in Chicago
Lincoln Park, one of Chicago’s best neighborhoods

Downtown Chicago is lively and filled with some of the best attractions the city has to offer. Still, Chicago is SO much more than the Loop and areas like River North and Streeterville. 

It’s a city comprised of cool neighborhoods with a lot to offer, so don’t be afraid to leave downtown to explore off the beaten path! Neighborhoods like Lincoln Park, Wicker Park, Hyde Park, and Old Town are great places to begin.

Check major holidays and city events before you book

Colorful sign of the Lollapalooza in Grant Park
Grant Park closed off for Lollapalooza

Before visiting Chicago, be mindful of any major holidays or citywide events that may take place during your trip. Specifically, look out for events that take over Grant Park. These include Lollapalooza, Chicago Blues Festival, and Taste of Chicago. The Chicago city center becomes crowded during these times, making it difficult to visit certain attractions.

Save money with CityPass

A couple taking a selfie at the Skydeck in Willis Tower
Step out onto the Skydeck at Willis Tower! (photo: Thomas Barrat / Shutterstock) 

If hitting up Chicago’s top attractions and museums is high on your list, I highly recommend purchasing a Chicago CityPass. For a discounted flat rate, city passes will give you access to many must-visit sites. These include the Shedd Aquarium, Skydeck Chicago in Willis Tower (formerly known as the Sears Tower), and the Field Museum. 

You’ll also be granted entry to two of the following: the Art Institute of Chicago, Museum of Science & Industry, 360 Chicago Observation Deck in the John Hancock Center, and Adler Planetarium. 

Take advantage of free activities and attractions

View of the Tiffany Dome in Chicago Cultural Center
Tiffany Dome inside the Chicago Cultural Center

Chicago has tons of free attractions and activities, so be sure to take advantage of them! Some popular ones include the Lincoln Park Zoo, Lincoln Park Conservatory, Chicago Cultural Center, and Harold Washington Library Center. And of course, it’s free to explore iconic places like Millennium Park and the Magnificent Mile on Michigan Avenue. 

Don’t skip out on Chicago’s waterfronts

View from the outside of the Adler Planetarium
View from the Museum Campus area outside of Adler Planetarium

As beautiful as downtown Chicago is, don’t overlook the city’s waterfronts! Stroll the Riverwalk along the Chicago River for picturesque views or take a Chicago river boat tour.

You can enjoy Lake Michigan by either walking or using the city’s bike share program along the Lakefront Trail. Here, you’ll find tons of great spots for seeing the Chicago skyline. If you’re looking for a Lake Michigan beach day, head to Oak Street Beach or North Avenue Beach.

Check on museum discounts

View of a class on a school trip buying their entrance pass on a museum

Many museums in Chicago offer discounts to select patrons. These include students (bring your ID!), seniors, and Illinois residents. Occasionally, teachers and veterans are also eligible. Museums also offer occasional free museum days, so be on the lookout for those, too.

Trust your gut and use common sense when it comes to safety

Buildings around the River North at night
River North at night

At the end of the day, Chicago is still a major city. This means that although visiting is generally safe for tourists, crime can happen. While traveling, stay vigilant and always be mindful of your surroundings. When it comes to Chicago safety, trust your gut and use common sense. 

Chicago businesses may charge additional fees

A cup of coffee, a pen, a receipt, and a credit card on a table

On your visit to Chicago, be prepared to pay some additional fees or higher fee rates than you’re probably used to. Sales Tax is 10.25%, and the Hotel Accommodations Tax is 17.4%. Some restaurants also charge a surcharge (typically about 3%) in addition to tax and tip. This covers things like health insurance for their employees. 

Chicago driving “etiquette” is a little different

View of cars driving in Chicago under the clear blue sky

I’ll be honest, driving in Chicago is a different experience than driving in say, the suburbs. This being said, it’s definitely doable if you know some things ahead of time. 

First of all, city driving is obviously more chaotic, so be prepared for some impatient drivers. Chicago drivers occasionally swerve in and out of lanes, so be aware of your surroundings. Lastly, don’t be surprised if you don’t see too many turn signals being used.

Be mindful of homelessness

A homeless man sleeping on a public bench in Chicago
(photo: Page Light Studios / Shutterstock)

Like any major city, Chicago has a decent-sized homeless population. You’re likely to encounter homeless people around the city and sometimes on public transportation. Just be mindful that this is an unfortunate reality for many people. Although most situations will be fine, always listen to your gut when it comes to safety. 

FAQs About Visiting Chicago

Is Chicago unsafe for tourists?

Chicago is not unsafe for tourists. Like any city, Chicago has its fair amount of crime, but this typically happens in outlying areas. Popular neighborhoods like the Loop and River North are where most tourists spend their time. These areas are highly populated, well-lit, and quite safe.

How do you travel in Chicago?

Public transportation is the best way to get around Chicago. The public transportation in the city is organized, reliable, and easy to navigate. 

Is Chicago a walkable city?

Compared to many U.S. cities, Chicago is highly walkable. You may have to take public transportation to different neighborhoods or specific attractions. But if you’re exploring one particular area like the Loop, River North, or Lincoln Park, you’ll find it’s extremely walkable.


Chicago is (in my humble opinion) one of the best cities in America. Hopefully, these Chicago travel tips helped you feel more prepared for your visit!

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