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33 BEST Chicago Travel Tips From a Local for First-Time Visitors (in 2024)

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As a Chicago native, let me be the first to give you a warm welcome to my city! It’s a great place with superb architecture, fine food and many nicknames: Second City, Windy City, City of the Big Shoulders, to name a few. And these Chicago travel tips will help you enjoy this city in all its glory.

Repeatedly named best big city in the United States by Condé Nast Traveler, it’s no surprise Chicago is on your list of must-travel cities! As someone who was born in and is now living in Chicago, let me give you my top Chicago travel tips for mistakes to avoid while you’re in this major city to make your Chicago trip a great one.

I’m talking about the best things to do in Chicago and the worst, places to see in Chicago and ones to avoid.

Follow these Chicago travel tips for smooth sailing. The useful travel tips for Chicago covered in this Chicago travel guide are important things to know when planning on visiting Chicago for the first time — all from the perspective of a Chicago native. 

Planning a trip? Use my go-to resources:

Jump ahead to:

TOP Chicago Travel Tips: 33 Do’s and Don’ts of Visiting Chicago for the First Time

1. Renting a Car

Chicago Trip Public Transportation Chicago Travel Tips Chicago travel blog post

As you plan your visit to Chicago you’re likely wondering how you’ll get from place to place. Chicago’s public transportation system is one of the largest you’ll come across in the US.

It’s highly convenient to get around by bus or l train here using a Ventra card, and you can find fare information alongside other transit tips here.

Driving in the city can be overwhelming and you’ll easily waste valuable vacation minutes searching for reasonable parking. Public transit is a great way to get around Chicago and it’s a good idea to plan accordingly.

If you prefer car travel, stick with taxis and ride-shares. Unless you’re planning a day trip that’ll take you outside of Chicago, no need to rent a car here.

Besides, if you’re anything like me the best way to take in a new city is on foot anyway! Or, rent a Divvy bike from one of the many stalls across the city.

Even better, take a guided Chicago bike tour led by a local for a fun and unique way to experience Chicago!

2. Skipping the Deep Dish Pizza

Travel to Chicago for Deep Dish Chicago Style Pizza, must do in Chicago!

Forget what the haters say, you can’t leave Chicago without trying our deep-dish pizza! Some love it (me!), others love to hate it so take the plunge into a thick, cheesy slice and be your own judge.

Not sure where to start? In my opinion Giordano’s is one of the best places for a slice of deep dish pizza, but everyone has their own thoughts on this. Others swear by Lou Malnati’s. Read my guide for where to get the best deep dish pizza in Chicago, here.

Some establishments are known for a crispier crust, others for the size of a slice and still others for their sauce. The only way to really uncover your favorite is to try them all when you travel to Chicago. I won’t judge!

And if you’re really big on foodie travel, sign up for a Chicago food tour! This would be a delicious addition to your Chicago trip itinerary!

3. Missing out on Gourmet Donuts

things to do in Chicago, try gourmet dounuts
Photo by marina shana on Unsplash

Who knows why or how Chicago became home to a growing gourmet donut scene? Don’t question what’s good, I always say.

Swing by any one of these sweet spots for a fancy Chicago donut and smooth cup of coffee.

My personal favorite? A lemon pistachio old-fashioned from Stan’s with a cup of their coffee to cut the sweetness. Bite, sip, bliss.

Sign up for this Underground Donut Tour if you want a guide for your sweet adventure!

4. Sidestepping Museum Campus

Visit Chicago Museum Campus for skyline views Chicago Travel Tips

As a certified museum avoider, I won’t blame you for not wanting to spend hours of vacation time inside. Chicago has some great museums but, unless you’re taking a longer trip or the weather is crummy I say don’t wile away your days indoors. Still, a visit to museum campus itself is well worth it.

Spend some time out in the park for some of the best skyline views Chicago has to offer. Have enough time to really explore the museum scene?

You’ll find no shortage of options including: The Museum of Science & Industry, Field Museum, Adler Planetarium, Shedd Aquarium, Art Institute of Chicago — truly something to fulfill any interest.

5. Neglecting to Venture outside of the Loop

free things to do in Chicago explore Chicago neighborhoods
Photo by Pedro Lastra on Unsplash

Chicago has 77 different neighborhoods but if you’re not from around here, you’re probably most familiar with the Loop or downtown Chicago.

There are plenty of worthwhile attractions in the Loop, and if you’re willing to venture outside of downtown there’s even more for you to discover.

Get a feel for all the different neighborhoods here, or check out the ‘Beyond the Loop’ video series for inspiration.

If you’re looking for free things to do in Chicago, add neighborhood-hopping to your list.


6. Not Visiting During Summer Months

best time to travel to Chicago in summer
Photo by Robert V. Ruggiero on Unsplash

You’ve heard the horror stories, right? Chicago’s winters are not to be messed with. They’re bone-chillingly cold, face-bitingly windy and seem to go on forever.

While Chicago is gorgeous any time of year, you’re better off visiting us in the summertime. This city and all its people come to LIFE in the warmer months.

After spending most of the year coated in frost and bundled in layers, both the nature and the people of Chicago are renewed in summer.

Come enjoy the many patios, rooftop bars, beach days, gorgeous blooms and sunny skyline views we have to offer. Visiting Chicago should top your list of summer destinations, no question.

If you really want to avoid visiting during peak season, early fall is the second best time to visit Chicago.

All that said, if you do somehow find yourself en route to Chicago in the winter then follow the tips in this Chicago winter survival guide!

7. Ignoring the Rooftop Bars

Visit Chicago at Night Chicago Travel Tips things to do in Chicago at night

There are plenty of eye-level restaurants and bars to lure you in as you walk the city streets, but don’t forget to elevate your experience by checking out Chicago’s rooftop scene.

Whether you’re looking for a panoramic views of the city and Lake Michigan with great drinks or food, this city has something special in store for you.

Personal favorites of mine (all featured on the lists linked here) are: Cindy’s Rooftop, The J. Parker and Bernie’s Lunch & Supper. If you’re looking for things to do in Chicago at night, you can’t beat taking the city lights from up high.

8. Staying on Land the Entire Time

Chicago Travel Tips Visit Chicago Architecture River Cruise

My most recommended activity to visitors is a Chicago architecture river cruise along the Chicago River. There are a variety of providers and I’ve yet to have a bad experience with any of them, but if you’re looking for the original then sign up for this one led by the Chicago Architecture Center itself.

This is a can’t-miss Chicago tourist attraction for all and even the locals love it. Grab a drink or bite to eat on the Riverwalk before or after to round out the experience.

9. Forgetting Garrett’s as Souvenirs

Chicago-style popcorn? It’s a thing, and you’ll find it at Garrett Popcorn Shops. It’s an easy souvenir or gift, and you can even have it shipped back home if you don’t want to lug a full tin around. Get the Garret Mix for a fool-proof blend of cheddar and caramel.

10. Laughing off the Comedy Scene

This city has turned out some leading comedians, and it’s worth your while to catch a show while you’re visiting Chicago.

The Second City is a no-brainer, known for launching the careers of Tina Fey, John Belushi and Steve Carell, to name a few. Buy your tickets for an upcoming show then eat, drink and laugh your way through a fun time!

11. Coming Without a Must-Eat List

Chicago’s food scene is top notch, and you won’t want to miss out. Don’t let overwhelm lead you to eat at chain restaurants (unless it’s Portillo’s).

Instead, do some research and plan ahead a bit. Where possible, make reservations before your trip.

Especially if you’re planning to dine at one of the best restaurant in the West Loop or River North neighborhoods. Not sure where to begin? Start here. No question, eating well is a must-do in Chicago.

12. Prioritizing Navy Pier

Chicago Travel Tips Visit Chicago Navy Pier

A long-held tourist hot spot, most locals will be quick to tell you Navy Pier is not really worth the visit. It’s overpriced, crowded and small without much to really do.

Instead, spend some time wandering through Millennium Park, strolling and eating along the Riverwalk or biking the Lakeshore path.

There are plenty of green spaces and beaches alike from where to enjoy this great city, so skip the tourist trap that is Navy Pier.

13. Skipping Wrigley Field

Visit Chicago Wrigley Field Chicago tourist attraction Chicago travel blog

Whether you’re a baseball fan or not, Wrigley Field is an iconic site in Chicago. Especially after the Cubs broke their 108-year streak in 2016 and won the World Series championship there.

At the very least, visit the stadium and snap a picture before exploring the food and drink scene in the area.

Have more time on your hands? Show up and see if you can snag affordable, last-minute tickets for an ongoing game. Note that Chicago has two baseball teams, you could also opt for a White Sox game instead.

14. Adding Ketchup to Your Hot Dogs

The Chicago-style hot dog is an all-beef hot dog nestled in a poppyseed bun and topped with mustard and relish. That’s all you need — do not ask for ketchup.

That’s just not the way it’s done here. See here for a list of the best places to try Chicago-style hot dogs.

15. Ignoring the West Loop Dining Scene

It can be easy to spend all your time in the heart of downtown Chicago has a visitor to this city but only minutes away from the central downtown area in the West Loop neighborhood you’ll find some of the best restaurants in Chicago.

Start here for a list of must-eats in the West Loop to decide where you want to make your reservations.

16. Forgetting to go Window Shopping Along Michigan Avenue

Alright, let’s be honest if you’re visiting Chicago then you’re bound to end up on the Magnificent Mile at some point.

But just in case it’s not already on your radar, a stroll along the Mag Mile is a must. Apart from the shopping, you’ll come across some iconic views including one of the castle-like Chicago Water Tower.

18. Bypassing the Chicago Observation Deck at Willis Tower

Chicago skydeck view

Ask any native Chicagoan and they’ll likely say the real mistake is calling it Willis Tower. At least, that’s what you’d hear from those of us who grew up calling it the Sears Tower.

Regardless, this is one of Chicago’s longer-standing tourist attractions and has received many modern upgrades over the years. Worth checking out for the sweeping 360 city views from atop this tallest building in Chicago.

19. Forgetting About the Beaches

Oak Street Beach Chicago

Yes, Chicago is a major city with a gorgeous skyline. But we also have beaches! Spend some time on the ever popular North Avenue Beach or Oak street beach off of the Gold Coast neighborhood.

You’ll also find cafes and restaurants on the beach, like Whispers Cafe near Oak Street Beach. It’s pretty incredible to sit on the sand, looking out at Lake Michigan in front of you with the Chicago skyline as your backdrop.

20. Not Taking Advantage of a Walking Tour

Chicago is one of the most walkable cities you’ll experience, and a guided walking tour is a great way to get to know it better. You can explore a free walking tour (remember to tip your guide, though!). If you’re wanting a more unique experience, consider booking one of these options:

21. Ignoring the Free Tours of the Chicago Cultural Center

Incredible architecture, free art exhibits and events, guided tours all await you at the historic Chicago Cultural Center. It first opened in 1897 and served as Chicago’s first public library.

The stained glass domes are a photographer’s dream. Read more on the free ways to enjoy this space.

22. Buzzing Over the Coffee Scene

Chicago has no shortage of delicious specialty coffee shops with quirky and cool decor. There’s a coffee shop for every vibe here and you’d be remiss to not explore and find the one that suits you best!

23. Keeping Your Ears Away from Live Music

Chicago has a music scene, too. From Al Capone’s old favorite, Green Mill, to the House of Blues in River North and everything in between music lovers can easily find a good place to have a great time here.

24. Forgetting to Factor in the Festivals

No matter what time of year you visit, you can bet there’s at least one event or festival to add to your Chicago travel itinerary.

There’s the age-old Taste of Chicago, Grant Park Music Festival, Zoolights at Lincoln Park Zoo, ice skating at Millennium Park in winter months, Chicago Blues Festival and so much more. Consult the full schedule by Choose Chicago to plan your trip.

25. Not packing properly

Although the seasons in Chicago are defined and predictable, on a day-to-day basis the weather can be surprising. You might have 70-degree (F) weather one day and snow flurries the next as the seasons transition.

You might have blue skies and then a cloudy cool day. Layers are your best bet when packing for Chicago.

If you’re venturing here in the winter, you’ll absolutely want layers and a warm enough coat. Warm enough for Chicago is not the same as warm enough for cold weather everywhere else.

Our winters are best described as bone-chilling on their worst days! Hats, gloves,

26. Missing the Magic of Buckingham Fountain

buckingham fountain light show free things to do in Chicago

One of my favorite childhood memories includes stopping by Buckingham Fountain in the evening anytime we had family visiting from out of town. We would go to see the light show and changing colors at this pretty fountain. A simple and sweet experience.

27. Not Seeking Out The Original Rainbow Cone

You might’ve seen photos of the delightful rainbow cone. This family-owned business with tagline: life’s too short for just one flavor is expanding its presence and now you have even more opportunities across the Chicagoland area to get a taste of the 5-flavor stack.

28. Expecting Malort to Taste Good

If you’ve heard of Malort, you’ll know this liquor is considered a rite of passage of sorts in Chicago. You should also know, it’s notoriously awful.

Chicagoans have a love-to-hate relationship with Malort and this Chicagoan personally has not yet been brave enough to try Malort herself. But if you decide to take the leap at least you know what to expect.

29. Forgetting about the Italian Beef Sandwich

Another top Chicago food that’s not always discussed as often as the deep-dish pizza or hot dogs is the Italian beef sandwich. Here’s where to try one.

30. Skipping the Niceties

Chicagoans are not immune to the Midwest charm. Here you’re likely to find your hellos and good-mornings reciprocated. You can ask for directions with confidence. Chicagoans are a kind and hard-working bunch.

31. Thinking Your Chicago Trip Has to Break the Bank

There are plenty of free ways to enjoy this beautiful city. You can explore the various parks and beaches, stroll through neighborhoods with all different vibes, attend free events and festivals, sit along the riverfront and admire the architecture.

In addition to the Chicago Cultural Center mentioned previously, you can also visit the Lincoln Park Zoo or botanic gardens for free. Don’t let your budget be your barrier to visiting Chicago.

32. Missing Out on Savings With the Chicago CityPass

To get the most bang for your buck consider a city pass that allows you to explore multiple attractions while saving money. I recommend the explorer pass for the best value.

33. Assuming Chicago is Not a Safe Place

downtown Chicago is it safe city

Many people associate Chicago with violent crime and question whether or not it’s a safe city to visit. I understand the fear, and I recognize that we all tend to fear the unfamiliar.

As long as you employ the same common sense you would in any other big city you’ll be safe — don’t leave your belongings unattended, don’t go out alone late at night, consider investing in an anti-theft purse, etc.

There you have it, these tips should set you up for a great trip as you prepare to travel to Chicago.

Where to Stay in Chicago

There are so many great hotels to choose from when looking for where to stay in Chicago. Here are some options for different price points, but be aware that seasonality does also affect prices:

🏨 Budget: Kasa Magnificent Mile

Kasa Hotel offers apartment-style accommodations in a great location. You’ll be within a 20-minute walk to two popular beaches, close to public transportation as well as to the city center.

👉 Click here to check prices and availability

🏨 Mid-Range: Allegro Royal Sonesta Hotel

This boutique, eco-friendly hotel is centrally located in the heart of downtown Chicago. In addition to its excellent location, the rooms are comfortable and the property has a well-equipped fitness facility onsite.

👉 Click here to check prices and availability

🏨 Luxury: The Peninsula

If you’re longing for luxury on your visit to Chicago book your stay at The Peninsula. In addition to its great location the hotel features an award-winning restaurant, renowned afternoon tea, a half-Olympic indoor pool, a gym with fitness classes, city views from an outdoor terrace and more.

👉 Click here to book your stay at The Peninsula

When is the best time to visit Chicago

Chicago bean covered in snow

If you’re hoping for great weather on your Chicago trip, then your best bet is to visit Chicago during summer months including late May through the end of August. Early fall is another wonderful time of year to visit Chicago.

Chicago in fall is truly beautiful and the weather is still quite pleasant. If you visit Chicago in September or October you’ll also see the beauty of autumn in Chicago and likely experience some shoulder season benefits like more affordable accommodations.

While winter in Chicago is not my personal favorite season, it’s quite nice if you enjoy the festive holiday season. Chicago has fantastic Christmas markets, beautiful ice skating rinks, delicious hot chocolate places and some lights-focused festivals.

Ultimately, it depends on what version of Chicago you’re most interested in exploring. Chicago is a great destination year-round!

What to Wear in Chicago

Layers are best, because the weather in Chicago can be a bit unpredictable. Generally, summertime sees women in dresses, skirts, shorts or jeans with casual tops in light fabrics. Men are usually in shorts and t-shirts or tank tops.

Fall in Chicago still sees some people in shorts as temperatures cool down — we Chicagoans don’t like to say goodbye to summer any sooner than we have to! But this is also when we see the resurgence of ankle boots and sweater season.

If you’re wondering what to wear in sunscreen is needed year-round. Even when you can’t see the sun during some Chicago winter days, it’s important to protect your skin from it. This is my personal favorite sunscreen at the moment.

How Many Days in Chicago Are Enough?

There’s plenty to do and see in Chicago in 2 days through a week. If you’re planning to spend most of your time in the city center, 2-3 days in Chicago should be plenty.

If you’d like to venture out and really explore Chicago neighborhoods outside of downtown, you might want to plan to visit Chicago for a week.

How to Get From the Airport to Chicago City Center?

If you’re coming from O’hare airport, you have the option of taking public transportation. Follow signs that say ‘train to the city’ or something to this effect and they will lead you to the Blue Line train that goes to downtown.

I highly recommend consulting google maps on your phone and following the route it outlines to your exact destination.

You also have the public transportation option if you’re coming from Midway airport. From there, you’ll take the Orange Line train. If you’re traveling light and not in a rush, public transportation is the more affordable option.

Uber, Lyft and taxis are also options from either airport. Simply follow the signs to the designated pick up points for each. Note that O’Hare airport now has a shuttle to get you to Terminal 2 from anywhere else in the airport since that is where Ubers and Lyfts arrive.

What is the Best Way to Get Around Chicago?

Chicago has an excellent public transit system and is the preferred way to get around Chicago. You can also supplement public transit with ride-share options like Uber and Lyft, or taxi rides (which can often be more affordable than ride-shares!).

Chicago is very walkable, so you’ll also be able to get around by walking in some areas.

How do I prepare for a trip to Chicago?  What do I need to know about traveling to Chicago?

Reading through this list of Chicago travel tips and what NOT to do in Chicago is a great way to prepare for your Chicago trip! Before you visit Chicago, take the time to determine exactly what you want to get out of your trip and plan accordingly.

Do you want to see the museums, when will you go? Want to eat at certain restaurants? Make those reservations in advance!

Chicago is a friendly city, and like any big city it’s important to always stay aware of your surroundings and take standard safety precautions. I know you will love Chicago, there is something for everyone here!

How to Eat Like a Local in Chicago?

There are the quintessential Chicago foods to try that we covered above, including: Italian beef, deep dish pizza, rainbow cones, hot dogs and so on. But Chicago has a huge foodie scene.

The best way to eat like a local in Chicago is to simply, eat! And of course, avoid the national chain restaurants if you can. If you’re exploring different neighborhoods, you’re sure to also learn a lot about their unique vibes by exploring their food scenes.

What is Chicago famous for?

If you’re still wondering why visit Chicago? Is it worth it to visit Chicago? Well, yes! Chicago is known for its down-to-earth people, its comedy scene, foodie status and awe-inspiring architecture.

You’re sure to discover your own personal reasons for loving the windy city when you visit.

What Chicago Travel Apps Should I Download?

A great app for anyone who takes public transportation in Chicago is the Ventra app. Having both Uber and Lyft apps downloaded on your phone is also helpful so you can check prices between each if you plan to take ride shares.

These days, taking taxis is often less expensive than ride shares. Download the Curb app for taxis.

If you do plan to do any driving around Chicago, Park Chicago is a great app that allows you to pay your parking fare remotely so you don’t have to physically return to feed the meter. Spot Hero is great for actually finding parking.

Accessibility, Emergency Services and Tipping in Chicago:

For even more helpful Chicago travel tips I highly recommend consulting this information by Chicago’s own tourism board!

Final Thoughts: Chicago Travel Tips By a Local

As a Chicago native I can confirm this really is a great city both for living in and for visiting. Follow these tips and have a great visit to my city!

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