16 Important Things to Know Before Visiting Chicago, Illinois

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Are you planning your first solo trip to Chicago, Illinois? Be sure to read this post before you visit!

From the ease of getting around, to the countless restaurants, Chicago is by far my favorite city to visit. I’ve already been four times and, as I write this, I have a fifth trip planned in just over a month.

While I can’t — and don’t — consider myself an expert on all things Chicago, I have made some mistakes I want you to learn from.

It’s my mission to take these mistakes and turn them into valuable, tangible advice that makes you go, “Wow, I’m glad I knew that before my trip!”

In this post, I’m going to share 16 Chicago travel tips and must-knows to help you plan the best solo trip possible. By the end, I hope you’ll have a few of those “wow” moments and be readier than ever to travel my favorite city.

Ready, friend? Let’s go to Chicago!

THIS POST IS ALL ABOUT THINGS TO KNOW BEFORE VISITING CHICAGO.

16 THINGS TO KNOW BEFORE VISITING CHICAGO

DON’T LET THE NEVER-ENDING HEADLINES DISCOURAGE YOU FROM VISITING

Before we get any further, I have to address an everlasting (but understandable) topic: is Chicago safe?

The fact of the matter is, Chicago is a major metropolitan city in America. And just like its peers — NYC, SF, Seattle, Boston and Philadelphia — safety is an ongoing concern.

You will always have to be cautious and weary when visiting a large city, especially as a solo traveler.

But please, and I repeat, PLEASE do not let the never-ending headlines discourage you from visiting.

Chicago is an amazing city, and I’d hate for you to avoid going just because people are trying to talk you out of it.

Just know that I will never do that. I’ll come straight to you with the facts so you can make an educated, informed decision.

I’m considering writing a full guide where I discuss whether Chicago is safe to visit. Let me know if that’s something you’d be interested in! I might even make it a series and write that kind of guide for every destination I cover.

Read this post for more solo travel safety tips.

CONSIDER PLANNING YOUR TRIP AROUND ONE OF CHICAGO’S ANNUAL EVENTS

If you didn’t know, Chicago hosts a rather absurd number of yearly events — many of which are free.

I don’t plan trips around events too often, but Chicago is an exception. The good thing is, there are all sorts of events each season.

So whether you visit during summer or winter, you’ll be sure to find something exciting to partake in.

Here are just a few of Chicago’s annual events:

• Taste of Chicago
• Lollapalooza
• Chicago Jazz Festival
• Chicago Blues Festival
• St. Patrick’s Day River Dyeing
• Chicago Ducky Derby
• Faces of Fitness Chicago

I could go on and on, but to save your eyes and ears, consider following a few accounts on Instagram to stay in the know.

@chicagobucketlist, @chicago_forfree and @do312 are some of my favorites. I always check them when planning a trip to The Windy City.

TAKE ADVANTAGE OF WALKING & PUBLIC TRANSPORTATION

Chicago has a walkability score of 77%, which is higher than most cities, including major ones like Los Angeles.

In fact, the city is consistently ranked third-most walkable in the US, just behind SF and NYC. So you better believe it when I say getting around is easy (and cheap, must I add).

Even if you want to go a bit further and explore one of Chicago’s seventy-seven distinct areas (which you totally should), you can easily get there by taking public transportation.

Chicago has a full, extensive public transit network called CTA, which stands for Chicago Transit Authority.

There are 127 bus routes and eight rapid train lines, with more routes and stops regularly being added.

Consider getting an unlimited pass if you plan on heavily using public transit during your trip.

The CTA has some of the best, most competitive rates for these passes. A one-day pass costs $5 and a three-day pass costs $15. Both give you access to all bus and train routes, with free transfers within two hours.

You could very much spend five days in the city and not take a single Uber or Lyft. The transit is just that good! I promise I’m not an official spokesperson or anything (although I’d happily accept the offer).

Consider reading my guide on getting around Chicago if you’re interested. In it, I go into further detail about the best ways to navigate through the city.

USE THESE APPS FOR GETTING AROUND

To piggyback off the previous tip, I suggest that you download a few special apps for getting around Chicago:

• Google Maps: the king of directions. This great for driving, along with public transit wait times and fares.
• Citymapper: this is my favorite app for walking directions. The directions are SO much more helpful than Apple Maps.
• Transit: great for public transit directions, fares and wait times. These are often a bit more accurate and rapidly updated than Apple Maps or Google Maps.

WEAR GOOD WALKING SHOES

I promise this is the last tip regarding transportation. I must reiterate that Chicago is highly walkable, so you’ll likely be walking a lot during your trip.

And while that’s great, please remember to wear some good walking shoes. You don’t want to end your trip realizing there are blisters on your feet.

I like the Hoka Bondi 9 shoes. They weren’t too expensive and literally feel like I’m walking on clouds, they’re so bouncy. Consider buying these or reading this guide for the best travel shoes.

THE DOWNTOWN AREA IS COOL, BUT DON’T HESITATE TO CHECK OUT OTHER NEIGHBORHOODS

Chicago is often called the city of neighborhoods, which makes sense considering there are 77 of them.

The downtown area is called The Loop. Why? Because all of the trains (called the “L”) meet or “loop” there. Pretty clever, innit?

While there’s TONS to do in Downtown Chicago — like an architecture river tour and The Art Institute — that’s not all the city has to offer…

Consider venturing out into a neighborhood like Wicker Park, Andersonville, Lincoln Park or Logan Square. Here, you’ll have a much more local experience with lots of bars, boutique stores and restaurants.

YOU WON’T FIND THE BEST FOOD IN DOWNTOWN CHICAGO

This may not come to your surprise, but the best food isn’t located in Downtown Chicago.

Sure, you’ll find some iconic spots like Portillo’s and Al’s Beef, but if you’re looking for the GOOD spots, you’ll have to look elsewhere.

I’m afraid there’s no universally-agreed “best foodie neighborhood” in Chicago, but contenders include Bucktown, Logan Square, Wicker Park and Lake View.

DON’T STOP IN THE MIDDLE OF THE SIDEWALK

Oh my goodness, please don’t do this. I can’t stand it when I’m walking and someone abruptly stops in front of me. It makes me want to rip my hair out.

If you must stop for a second to check your phone or take a bite of that delicious Chicago-style hot dog, step to the side.

DON’T EVEN BOTHER TRYING TO STUFF EVERYTHING INTO A THREE-DAY ITINERARY

Look. Chicago is a big city with countless things to do and you’d (respectfully) be a fool if you think you can do or see it all in one short trip.

If anything, I think it’s much better to keep your itinerary realistic and stick to a handful of special experiences.

That way, you’ll still have stuff to do on future trips (because trust me, you’ll want to go back time and time again).

If you’re worried you’ll miss the essentials, don’t worry. I include them in my three-day Chicago itinerary here. Check it out if you’re planning your first solo trip to the city.

PACK LAYERS IF VISITING DURING SPRING OR WINTER

These are the city’s shoulder seasons and if you didn’t know, Chicago experiences all four seasons — sometimes in just a few hours!

And I’ve lived in Illinois my entire life, so I know what I’m talking about. It’s actually quite annoying, but I won’t get into that right now.

Just know that if you’re visiting during spring or winter, you need to pack layers. ESPECIALLY for winter. Temperatures get painfully low, and I’d hate for you to freeze your ears off because you didn’t pack correctly.

PACK SWIM GEAR

Yes, pack swim gear for Chicago. The city has 26 free public beaches, including Oak Street Beach, Ohio Street Beach and North Avenue Beach, which are some of my favorites.

Trust me, you’ll want to take a dip in the water during the hot, humid summers.

FIND A HOTEL BASED ON WHAT YOU’RE DOING

I believe that, in order to maximize efficiently, you need to base your hotel on what you’re doing.

For example, if you’re visiting the Art Institute, Millennium Park and Field Museum, you’ll probably want to stay in South Loop. If you’re attending a Cubs game at Wrigley Field, though, you might want to stay in Lake View instead.

It’s smart to do this so you don’t spend extra time transporting through the city. As a PTO traveler, you likely don’t have a bunch of time to travel, and I’m sure you’ll want to make good use of the time you do have.

IF NOTHING ELSE, MAKE SURE YOU DO THE ARCHITECTURE RIVER CRUISE

There’s probably one activity both locals AND tourists enjoy: the architecture boat tour. If you’ve done even just a small amount of research so far, you’ve probably stumbled upon this.

It’s basically a 45 to 120-minute cruise on the Chicago River that takes you through the city while a volunteer teaches you about the architecture.

And while that might sound a bit uneventful to some, it’s an absolute must-do for your first trip. Because even if you don’t care for architecture, the experience itself is worth the time and money.

TIP A FAIR AMOUNT TO WAITERS & HOUSEKEEPERS

15-20% is a good percentage for waiters and a few dollars is adequate for housekeepers, so long as the service is good, of course!

IT’S POSSIBLE TO VISIT CHICAGO ON A BUDGET

I’m sure you’ll be happy to hear this if you typically travel on a budget.

Chicago is one of the cheaper major cities compared to Los Angeles and New York. And even with this being the case, there are several things you can do to maximize your money in Chicago:

• Buy an attraction pass like CityPASS or Go City Chicago. These passes can be a great bang for your buck since they bundle activities instead of you having to buy each individually. Just be sure to do your research and confirm you’re actually getting a deal. Use the Attraction Pass Decision Tool in the TSS Freebie Library for help!
• Visit popular attractions during off-peak hours. If you’ve already started planning your first solo trip to Chicago, you’ve probably noticed that the prices for certain places like 360 CHICAGO and the Museum of Ice Cream change depending on time of day. Try to visit during the less busy hours to save a few dollars. On top of saving money, there won’t be as many people there, which is a win-win situation in my book!
• Use public transportation. I already touched on this earlier, but I figured it didn’t hurt to reiterate that you can easily save $80-100+ on Ubers if you utilize the city’s public transit network, CTA. It’s not difficult to learn and fairly reliable.
• Stay in a cheaper area. Yes, Gold Coast and Streeterville are nice, but those are some of the more expensive areas to stay during your trip. If you’re visiting Chicago on a budget, I recommend staying in South Loop instead, as the hotels and guesthouses here are a bit more affordable. Read my full accommodations guide here for all of my recommendations.

…and those are just a few ways to save money in The Windy City. Read my budget travel guide for more tips. In it, I share over 40 tips for saving money when traveling.

BRING CASH

While you can use your credit in many restaurants and bars, there are quite a few places — including the food trucks — that may only take cash. I recommend bringing about $20-50 in cash for those instances.

Consider getting the Charles Schwab debit card before your trip to save money on ATM fees. This is a popular debit card in the travel community because they never charge any ATM or foreign transaction fees.

FINAL THOUGHTS: CHICAGO TRAVEL TIPS

In this post, I shared 16 Chicago travel tips and must-knows. I think it’s important that you’re aware of these so you can be fully prepared to visit the city.

Please let me know if any of these travel tips helped you!

Now, friend, it’s your turn. I’m opening the floor for you to start a conversation in the comments. Here are some discussion topics:

• Are you currently planning a trip to Chicago? What phase are you in? Are you just thinking about it or have you already created an itinerary? Let me know if I can help!
• Have you been to Chicago before? What mistakes did you make and take note of so you don’t make them again?
• What travel tip in this guide made you go, “Wow, I’m glad you said that?”

I’d love to hear your thoughts! If you feel more comfortable chatting with me directly, shoot me a DM on Instagram or email me at demarcus@thesolosolstice.com.

ABOUT DEMARCUS

DeMarcus is a Midwest-based travel content creator and the founder of the solo travel blog, The Solo Solstice. He began his solo travel journey in December 2025 and since has been creating practical, in-depth travel guides for a like-minded community of first-time solo adventurers.

Visit the About Page to learn more about DeMarcus, and visit the Ethical & Responsible Tourism Page to learn more about his efforts to promote responsible tourism.