20 Chicago Travel Tips & Things to Know (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 top Chicago attractions in one day, and 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 the Lincoln Park Zoo and 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 the 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.

🖨️ Get a free, printable version of our Chicago itinerary here!

Take Public Transportation

Overlooking view of the "L" running through the Loop — *The “L” running through the Loop (photo: EarthScape ImageGraphy / Shutterstock)*

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 hot take but don’t feel like you have to try all the Chicago food staples like deep dish pizza or a Chicago-style hot dog. Chicago is full of so many incredible restaurants with every cuisine imaginable, so don’t feel like you have to limit yourself!

However, if you do want to try the classics, Pequod’s Pizza and Lou Malnati’s are great options for deep-dish pizza and Portillo’s is a go-to spot for hot dogs.

For more, check out my full Chicago food guide.

Wear Good Walking Shoes

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

You’ll find that sneakers are the go-to shoe for most Chicagoans. I recommend that you hop on board during your visit. 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 — *(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!

And if you’ve just moved here or are thinking about it, know that there are tons of ways to make friends in Chicago, too.

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*

Be sure to check the hours of any attractions and places you plan on visiting if a Monday is a day you’ll be in Chicago. Many places like the Art Institute of Chicago, Museum of Contemporary Art Chicago, and Chicago History Museum are closed on Mondays. The same applies to many small businesses. Plan ahead to avoid hassle and disappointment!

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)*

Covid mandates may or may not be in place in Chicago, depending on the state of the pandemic. 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*

Reservations are highly encouraged (and sometimes required) at most Chicago restaurants. 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. Note that there may also be additional patio fees if you plan on visiting a riverside restaurant in the summer and sitting outside.

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!*

Chicago really hits each end of the spectrum when it comes to weather, from the frigid temperatures of winter to the blistering heat in summer. Check the weather and pack appropriately before visiting. 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 — *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.

Chicago’s amazing neighborhoods have a lot to offer. 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*

Be mindful of any major holidays or citywide events that may take place during your trip. Specifically, look out for events that take over downtown Chicago and Grant Park. These include Lollapalooza, Chicago Blues Festival, and Taste of Chicago. The 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)*

I highly recommend purchasing a Chicago CityPASS if hitting up Chicago’s top attractions and museums is high on your list.

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, the 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*

There are tons of free attractions and activities in Chicago, so be sure to take advantage of them!

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*

Don’t overlook Chicago’s waterfronts. Chicago is home to a beautiful river and a stunning Lake Michigan coastline. It would be a mistake to overlook them!

Stroll the Riverwalk along the Chicago River for picturesque views or take a Chicago river boat tour. You can enjoy Lake Michigan by 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.

Head to Oak Street Beach or North Avenue Beach if you’re looking for a Lake Michigan beach day.

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 and Chicago 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*

Chicago is still a major city at the end of the day. This means that although visiting is generally safe for tourists, crime can happen. Stay vigilant and always be mindful of your surroundings. Trust your gut and use common sense when it comes to Chicago safety.

Chicago Businesses May Charge Additional Fees

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

Be prepared to pay some additional fees or higher fee rates than you’re probably used to when dining in Chicago. Sales Tax is 10.25%, and the Hotel Accommodations Tax is 4.5%. 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 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 people don’t use their turn signals.

Be Mindful of Homelessness

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

Chicago unfortunately 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.

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Hopefully, these tips help you feel more prepared for your visit! Chicago is (in my humble opinion) one of the best cities in America and I hope you love it as much as I do. Next, read my guide on day trips from Chicago for more adventures in the Midwest!