Traveling to Chicago: What You Really Need to Know Before You Go

Traveling to Chicago soon? Let me help you skip the rookie mistakes.

If you’re heading to the Windy City for the first time, this is the guide I wish I’d had when I started planning.

It’s not a list of Chicago attractions or touristy things to do (but I do have them if you need them).

This is more like a chat with someone who’s done the homework for you.

I’m sure you have many questions, as many do when visiting a big city.

Let’s admit, cities are exciting, but they are also a lot of work, and the more planning you can do before you go, the better.

I’m here to walk you through the stuff that matters—the honest, down-to-earth tips that’ll help you feel confident and relaxed while you’re exploring.

So grab your favorite drink, pull up a chair, and let’s have a chat.

Traveling To Chicago: What You Need To Know Before You Go

Don’t Rent A Car Unless You Have To

Traveling to Chicago with a rental car is usually more trouble than it’s worth.

Between aggressive traffic, expensive parking, and lots of one-way streets, it can get stressful fast.

Unless you’re planning a scenic road trip outside the city (like Indiana Dunes or Starved Rock), you’re way better off using public transit.

The CTA (Chicago Transit Authority) runs the “L” trains and buses that will take you just about everywhere you need to go.

I love walking in Chicago, it’s a great city for that. So my advice leave the car behind.

Get the Ventra App

The Ventra app is a game changer. You can load money onto it and buy unlimited passes, and track buses or trains in real-time.

It’s way easier than fumbling around at station kiosks, especially after a long day of sightseeing.

If you’re staying for a few days, grab a 3-day or 7-day CTA pass.

It’ll save you money and take the pressure off figuring out individual fares.

Traveling To Chicago: Understand The Neighborhoods

Chicago isn’t just one giant downtown, it’s a patchwork of neighbourhoods, each with its personality.

The Loop is where you’ll find most “Chicago must-see” landmarks like the Bean and Art Institute.

Logan Square or Wicker Park is where you will find indie shops, murals, and great food.

Knowing a bit about the layout can seriously help with planning.

For example, staying in River North or the West Loop gives you easy access to restaurants and nightlife.

Lakeview and Lincoln Park are a little more relaxed.

Pick a hotel that is close to the neighborhood you will spend most time in.

Watch The Weather Like A Hawk

Chicago’s weather can be, let’s say, dramatic. Yes, it’s windy, but that’s just the beginning.

You need to be prepared for everything here. The trick is layers.

Pack things that you can easily carry and put on or take off according to the temperature.

Even in summer, bring a light jacket or oversized scarf you can stuff in your bag. And if you’re coming in winter?

Go full Arctic chic puffer coat, boots, gloves, the works.

Need help planning outfits? Here’s my go-to guide on what to wear in Chicago in the summer.

You’ll Be Walking—A Lot

Chicago is one of the best walking cities in the US. The streets are relatively flat, the sidewalks are wide,

There’s so much to see just by exploring on foot. Murals, architecture, pop-up markets, and food stalls are just a few of the things I’ve stumbled across on foot.

Comfy walking shoes are a non-negotiable. You’ll thank yourself when you’re halfway down the Riverwalk or hunting down coffee in Wicker Park.

I also opt for fashionable trainers as they go with just about anything.

When Traveling To Chicago: Don’t Skip The Lakefront

You might think of skyscrapers when you picture Chicago, but it’s also home to gorgeous beaches and a massive waterfront.

Lake Michigan honestly feels like the ocean, and the lakefront trail is perfect for walking, jogging, or just taking in the skyline.

If you’re traveling to Chicago between May and September, pack a swimsuit or towel, you might find yourself sunbathing at North Avenue Beach before you know it.

This is one of my favorite places to go and spend a morning or afternoon.

If you love people watching, like I do, it’s an absolute joy!

Here is what to pack for Chicago in Fall, Winter, Summer and Spring.

Safety Basics (That Actually Matter)

I’ve personally never had any problems in Chicago, but like any major city, you must stay vigilant.

The vast majority of touristy areas are perfectly safe during the day, and even into the evening; however here are some tips that are good to keep in mind

• Keep your phone tucked away on public transit, or better still, bring along a cell phone lanyard.
• Don’t wander side streets alone late at night.
• Double-check rideshare license plates before hopping in and if alone make sure someone knows where you are. (I send the photo of my driver/his license plate to a family member.)
• Walk with purpose (even if you’re lost). You will be surprised how much body language plays a part in safety.
• Don’t flash around expensive items.
• Get tamper-proof bags. This is the exact bag I use.
• Always be around of your surroundings.

If it’s your first time traveling to Chicago solo or as a small group, trust your instincts and lean on locals if you need help.

Midwesterners are friendlier than you might expect.

Museums Are Amazing—But Look For Deals

Chicago is home to some truly world-class museums, but the ticket prices can add up.

If you’re planning to hit a few in one trip, look for free admission days, especially if you’re with an Illinois resident.

Don’t forget to check out Chicago CityPASS for bundled attractions.

Food Is A Big Deal—But So Are The Neighborhood Eats

Sure, deep dish pizza is part of the Chicago experience. (Giordano’s, Lou Malnati’s, and Pequod’s are the big three.)

Here’s my review of the best places to find the best pizza in Chicago.

But don’t stop there. Chicago’s food scene goes way beyond tourist staples.

You’ll find amazing eats in tiny neighbourhood spots. From tacos and Korean fried chicken to pierogies and vegan soul food.

Ask a local, check Yelp, or just wander with an open mind.

You won’t go hungry. There are also some great food tours in the city which are a real treat.

Here are some of the best restaurants in Chicago.

Don’t Try to Do Everything When Traveling To Chicago

If you’re anything like me, your “Chicago sights” list probably started 50 items long.

Here’s your permission to trim it down. You don’t need to see everything to have a good time.

You’ll enjoy the city more if you don’t rush.

Focus on a few experiences that really speak to you, leave space for spontaneity, and save the rest for next time.

Here’s a great bucket list for Chicago to help you pick the ones that feel worth it.

Packing List Suggestions When Traveling To Chicago

No matter if you fly or drive to Chicago, read my tips on how to pack lightly in a carry-on.

This unisex RFID blocking concealed travel pouch is lightweight and comes in several colors.

These RFID Sleeves D sleeves are another perfect solution.

This Anker high-speed phone charging battery is the exact one I carry with me on all of my trips.

My daughter gifted me this FugeTek selfie stick and tripod setup for my birthday.

It has Bluetooth connectivity and is a breeze to use for taking selfies.

I never leave home on a trip without my Bobble filtration bottle. 

The replaceable carbon filter ensures fresh water whenever you need it.

This foldable water-resistant backpack would be great.

Not all beaches are created equally and these quick dry slip-on Aqua shoes will come in handy for the beaches in Chicago.

These men’s quick-drying trunks are essential.

For women, this one-strap one-piece bathing suit is amazing.

Consider bringing along quick-dry super-absorbent microfiber towels.

This wet-dry bag with handles is a good option.

These unisex polarized sunglasses come in a lot of lens colors and frame designs, and are extremely affordable too.

If you are fond of aviator-style sunglasses, these polarized aviators may interest you.

As an Amazon Affiliate, I earn from your qualified purchases.

Traveling To Chicago: Spend Smart—Splurge Where It Counts

Chicago can be budget-friendly, but it can also be expensive.

You have to plan a little more to make it more affordable.

Here are some quick ways to save:

• Use public transportation (seriously, CTA is a lifesaver)
• Alternatively, try a Hop-On Hop-Off Sightseeing Open-Bus Tour
• Stay in hotels outside the Loop
• Eat local instead of downtown chains
• Take advantage of free attractions like Lincoln Park Zoo or Garfield Park Conservatory
• Visit attractions later in the day when prices are discounted.

That said, it’s okay to treat yourself!

A rooftop cocktail, a ticketed show, or a river architecture cruise might just be the highlight of your trip.

Final Thoughts On Traveling To Chicago

If you’re traveling to Chicago for the first time, know this: it’s big, it’s beautiful, and yes it can be a little chaotic.

But it’s also welcoming, full of character, and packed with little moments you’ll remember long after you’re home.

Thinking of spending a weekend in Chicago here is a great itinerary.