Chicago Travel Guide: Best Things to Do, Eat & See

Chicago was one of those trips where I thought I knew what I was getting myself into. This Chicago travel guide is based on my own experience exploring the city, from figuring out that infamous Chicago wind to checking out attractions, trying local food, and exploring downtown. I had my plans, I had my hotel booked, and I was ready to explore the city. What I did not have was a proper understanding of just how cold Chicago could feel.

Thank you for reading this post, don't forget to subscribe!

As a Southern girl, I underestimated that Chicago wind. That wind almost blew me away literally. I was out there realizing very quickly that Chicago cold is a different kind of cold, and I probably should have done a little more research before packing.

Still, I had a really good time. I stayed downtown, explored some popular Chicago attractions, ate some of the city’s famous food, and got a little taste of what makes Chicago such a fun city to visit. Looking back, there are definitely things I would do differently next time, especially when it comes to the weather.

So if you’re planning your first trip to Chicago, here’s what I experienced, what I learned, and a few things I’d put on your list for your own trip.

Where I Stayed: Club Quarters Hotel Central Loop Chicago

I stayed at Club Quarters Hotel, Central Loop Chicago, located at 111 West Adams Street.

The location was convenient for exploring downtown Chicago, and the staff were very kind during my stay. One thing I will say, though, is that the room was TINY for two double beds.

Now, this was partly my fault because I am a Southern girl who apparently wasn’t prepared for how small some city hotel rooms can be up North. When you’re used to having more space, you might walk into a downtown Chicago hotel room and think, “Oh… so this is it?”

If you’re traveling with another person, especially if you’re bringing larger suitcases, definitely pay attention to the room size when booking. Don’t just look at the number of beds.

That’s a Chicago hotel tip I learned the hard way.

Chicago Food Experiences: What I Tried

One thing I knew before visiting Chicago was that I needed to eat.

Chicago has a serious food culture, so I wasn’t about to leave without trying some of the city’s classics. From deep dish pizza to Chicago-style hot dogs and Italian beef, there is plenty to try.

I also went to Harold’s, because if you know, you know. I’m always interested in trying places that have a reputation and are part of the local food experience.

And yes, I had deep dish pizza.

I cannot remember the name of the restaurant right now, but I will add it once I find it because I definitely want to give them their credit.

The restaurant was within walking distance of my hotel, which made it even better. Being able to walk somewhere, grab dinner, and head back to the hotel without having to arrange transportation was convenient.

My advice? Come to Chicago hungry. Don’t spend your entire trip eating at the same types of restaurants you could find at home. Try the foods Chicago is known for, but also leave room to explore the city’s different neighborhoods and food cultures.

CityPASS

If you’re planning a Chicago trip, I also recommend checking out CityPASS, which bundles admission to some of the city’s top attractions and can help you save compared with buying individual tickets. As a CityPASS affiliate, I may earn a commission if you purchase through my link, at no additional cost to you.

Museum of Illusions Chicago

One of the attractions I visited was the Museum of Illusions.

This was such a fun stop because it isn’t your typical museum where you’re quietly walking around looking at exhibits. A lot of the experience is interactive, and you can really have fun taking pictures and playing around with the different optical illusions.

If you’re traveling with friends, this would be a fun place to visit together because you’re going to want somebody taking pictures of you.

And honestly, that’s part of what makes attractions like this fun for a city trip. You don’t always have to spend hours at one attraction. You can visit, have your fun, take your pictures, and continue exploring.

Navy Pier

I also made my way to Navy Pier while I was in Chicago.

Navy Pier is one of those places that you hear about before visiting Chicago, so of course I had to see what the hype was about. It’s a fun place to walk around, grab something to eat, shop, take in the lake views, and just enjoy being outside.

There are also attractions and entertainment throughout Navy Pier, including the Centennial Wheel. During warmer months, you can also enjoy boat rides and other activities along the waterfront.

I definitely recommend adding Navy Pier to your Chicago itinerary, especially if it’s your first visit.

Exploring the Chicago River: A Chicago Travel Experience

I also got to experience the Chicago River while I was there.

This is one of those moments where I wish I had taken better notes during my trip because I forgot just how much I actually did until I started putting this post together.

The Chicago River is such a big part of the city’s scenery. You have the water, the downtown buildings, the bridges, and all that beautiful architecture surrounding you.

If you’re visiting Chicago, make sure you spend some time around the river. Even if you don’t take a boat tour, walking around the Riverwalk and taking in the views is worth adding to your day.

Chicago Events to Know About

If you’re coming to Chicago to visit, there are several well-known annual events worth knowing about when planning your trip. From massive music festivals and food celebrations to cultural events highlighting Chicago’s rich Black history and arts scene, the city has something happening throughout the year.

Event dates can change from year to year, so be sure to check the official event websites for the current schedule before planning your trip.

Lollapalooza

One of Chicago’s biggest summer events, Lollapalooza is a massive music festival held in Grant Park. It attracts music lovers from around the world and features multiple days of performances across several stages.

Taste of Chicago

If you’re coming to Chicago for the food, Taste of Chicago is one event you’ll want to know about. Held in Grant Park, it’s one of the world’s largest food festivals and gives visitors the opportunity to sample food from restaurants and vendors throughout the city.

Chicago Air and Water Show

The Chicago Air and Water Show is a huge annual lakefront event held around North Avenue Beach. You can watch impressive aerial performances and water demonstrations along Chicago’s lakefront.

Chicago Blues Festival

Music lovers should also know about the Chicago Blues Festival, which is billed as the world’s largest free blues festival. The event takes place in Millennium Park and celebrates the blues tradition that Chicago is famous for.

Chicago Jazz Festival

The Chicago Jazz Festival is a free four-day jazz celebration held over Labor Day weekend. It brings together jazz musicians and fans for performances throughout the city.

Bud Billiken Parade

The Bud Billiken Parade is one of Chicago’s most significant annual cultural events and is held in August. It is the largest African American parade in the United States and has a long history of celebrating Black culture, community, education, and youth.

Chosen Few Picnic & Festival

For house music fans, the Chosen Few Picnic & Festival is a major Chicago event held in Jackson Park. It combines a large outdoor picnic with performances celebrating Chicago’s influential house music culture.

African Festival of the Arts

The African Festival of the Arts is a major celebration of African and African American arts and culture held in Washington Park, traditionally around Labor Day weekend. It features art, music, food, fashion, and cultural experiences.

Silver Room Block Party

The Silver Room Block Party is an iconic South Side community event featuring music, arts, fashion, vendors, and local culture. It’s a great example of the community-centered experiences visitors can find beyond Chicago’s traditional tourist attractions.

Black Creativity Exhibition

The Black Creativity Exhibition is an annual arts and science program at the Museum of Science and Industry that celebrates the creativity and achievements of Black artists, innovators, and creators.

Planning a Chicago trip around an event? These are just some of the annual events worth putting on your radar. If you want to experience a different side of Chicago, consider timing your visit around an event that matches your interests, whether that’s food, music, arts, culture, or Chicago’s vibrant Black community.

Things to Do in Chicago on My Next Trip

Even though I visited some of Chicago’s most recognizable areas, there is still so much I want to see.

So if you’re planning your own Chicago trip, here are some things on my next-trip list that you can consider adding to yours.

Millennium Park and The Bean

I definitely want to spend more time around Millennium Park and see Cloud Gate, better known as “The Bean.”

It’s one of those Chicago landmarks that you see in pictures all the time, but I’d like to take my time exploring the area instead of simply checking it off a list.

Chicago River Architecture Boat Tour

I saw the Chicago River during my trip, but next time I want to experience it from the water.

An architecture boat cruise is high on my list because Chicago is famous for its architecture, and seeing the buildings from the river gives you a completely different perspective.

Chicago Museums

If you love museums, Chicago has plenty to choose from. The Art Institute of Chicago, Field Museum, Shedd Aquarium, Adler Planetarium, and Griffin Museum of Science and Industry are some of the major attractions worth considering.

I definitely want to explore more of Chicago’s museums on my next trip.

DuSable Black History Museum and Education Center

This is another place I want to visit.

Chicago has such a deep Black history and culture, particularly on the city’s South Side. The DuSable Black History Museum and Education Center is a great option for travelers who want to learn more about African American history, culture, and contributions.

For Black travelers, I think it’s worth going beyond the standard tourist attractions and making time for the history and culture that helped shape the city.

Explore More Chicago Neighborhoods

I don’t want my next Chicago trip to be all downtown.

Chicago has 77 neighborhoods, and I want to experience more of them. That means trying more local restaurants, checking out different cultural areas, exploring neighborhood shops, and seeing how different parts of the city feel.

For Black travelers especially, I’d make time to experience some of Chicago’s Black cultural spaces, restaurants, music, history, and neighborhoods rather than only seeing the attractions that show up on every generic tourist list.

Spend More Time Along Lake Michigan

I also want to experience more of Chicago’s lakefront during warmer weather.

Chicago has beaches, waterfront parks, boat cruises, kayaking, water taxis, and other activities along Lake Michigan. If you’re visiting during the warmer months, there’s no reason to spend your entire trip indoors.

And yes, I would absolutely consider doing a boat activity next time.

I might even be bold enough to try something like kayaking.

Maybe.

Chicago Is a City for Food Lovers

If you are planning a trip to Chicago, please don’t just eat whatever you normally eat at home.

Try the food Chicago is known for.

Deep dish pizza is an obvious one, but don’t stop there. Try a Chicago-style hot dog, Italian beef, local fried chicken, and whatever other foods catch your attention while you’re there.

I also recommend checking out restaurants in different neighborhoods rather than only eating downtown. Some of the best travel memories come from finding a restaurant you weren’t expecting.

Best Time to Visit Chicago

Chicago: Find the best flights at Expedia.com

If you’re using this Chicago travel guide to plan your first trip, the weather is something I would pay close attention to. Let me save you from making my mistake.

I would not choose March for a first Chicago trip if you’re looking for comfortable weather.

March can absolutely be a fun time to visit, but the weather can still be cold and unpredictable. For me, the wind was the biggest issue. I was not prepared for it at all.

If you’re visiting Chicago for outdoor activities, walking around the city, enjoying the lakefront, and spending time at places like Navy Pier, I’d personally look at late spring, summer, or early fall.

Summer

June through August is a great choice if you want to experience Chicago outdoors. This is when you can really enjoy the lakefront, beaches, Riverwalk, boat tours, festivals, outdoor dining, and Navy Pier.

The downside is that summer can be busier, so expect more people and potentially higher prices.

Fall

Fall would probably be my personal choice for a future trip. You get cooler weather without necessarily dealing with that brutal winter feeling, and you can enjoy walking around the city without melting.

Spring

Late spring can be beautiful, especially as the city starts warming up and outdoor activities return. April and May can offer a better balance if you want spring weather without the full summer crowds.

Winter

If you love cold weather, snow, holiday events, and winter activities, Chicago can absolutely be beautiful during the colder months.

Me personally?

I’ll pass.

I’ve already learned my lesson.

Chicago Travel Guide: Travel Tips I Learned

Check the Weather Before You Pack

And when I say check the weather, I’m talking about the actual weather, not just the temperature.

Pay attention to the wind.

That Chicago wind had me questioning every decision that led me to that city.

If you’re traveling during a colder season, bring layers, a warm coat, gloves, and something to protect your ears. Comfortable shoes are also important because you’re likely going to do a lot of walking.

Don’t Assume Every Hotel Room Will Be Spacious

If you’re used to Southern hotels with plenty of room to spread out, don’t assume a downtown Chicago hotel room will be the same.

Look at the square footage before booking, especially if you’re traveling with another person.

Plan Your Days by Area

Chicago is a big city, so don’t plan your itinerary like everything is right next door.

Group attractions together by neighborhood or area when possible. You’ll spend less time going back and forth and more time actually enjoying the city.

Try the Local Food

Don’t come to Chicago and eat the same things you eat at home.

Try deep dish pizza. Try a Chicago-style hot dog. Try Italian beef. Check out local restaurants. Try something you’ve never had before.

Travel is about experiencing the place you’re visiting, and food is one of the easiest ways to do that.

My Coca-Cola Versus Pepsi Moment

Now let me tell y’all something that genuinely shocked me.

I ordered a Coca-Cola.

They didn’t have it.

They had Pepsi products.

Now listen. I grew up drinking Coke. I feel like I was drinking Coca-Cola in the womb. Coca-Cola is basically a Southern staple to me.

Then I had a conversation with a friend from up North who casually told me that she loves Pepsi and doesn’t fool with Coke like that.

I was FLABBERGASTED.

Like… what do you mean you don’t fool with Coke?

Apparently, I had some regional beverage assumptions that needed to be checked.

So if you’re from the South and you’re heading to Chicago, don’t be shocked if you run into some Pepsi loyalty.

These are some of the biggest lessons I took away from my Chicago trip, and hopefully they make planning your own trip a little easier. Consider this part of my Chicago travel guide for first-time visitors.

Final Thoughts on My Chicago Trip

My Chicago trip was definitely a learning experience. I hope this Chicago travel guide helps you plan a Chicago trip that gives you plenty of time to experience the city beyond the typical tourist stops.

I learned that I underestimated Chicago weather. I learned that hotel rooms in big Northern cities may be smaller than what I’m used to back home. I learned that I apparently have strong feelings about Coca-Cola. And I learned that one trip to Chicago definitely isn’t enough to experience the city.

I actually did more during that trip than I remembered, from visiting Navy Pier and the Chicago River to checking out the Museum of Illusions, eating Harold’s, trying deep dish pizza, and exploring downtown.

But there is still so much more I want to see.

I want to experience Chicago when the weather is warmer, spend more time outside, explore more neighborhoods, eat more food, learn more about the city’s history and culture, and finally get on one of those boats I’ve heard so much about.

So would I go back?

Absolutely.

Just not in March.

Next time, I’m checking the wind first.