Is Chicago Worth Visiting? 10 Reasons That’s a Yes

Known for architectural buildings such as the Sears Tower, its theatres, and food such as Chicago-style deep-dish pizza, Chicago is a city that millions flock to from all over the world. Almost 60 million people visit The Windy City annually.

With that kind of popularity, it’s hard not to want to check it out. However, you may also wonder, “Is Chicago worth visiting?”.

Chicago Downtown. Cityscape image of Chicago downtown during twilight blue hour.

I’ve visited Chicago once (twice if you count a quick trip for food, but we’ll get into that later). Although it was a short 2-day trip, the city left me awestruck.

There is, without a doubt, a lot to do and see. So much, in fact, that a couple of days may not seem like nearly enough time to fit in everything. While I didn’t get to experience all that I wanted, I checked a few items off my list. Would I return? Absolutely!

With all the good that Chicago has to offer, like any other tourist city, there are some drawbacks. Together, we will go over some of the cons as well as the many pros of why you should put Chicago on your travel destination bucket list!

Why you may not enjoy Chicago

The weather isn’t always the greatest

Cityscape with snowfall and street lights in the center of Chicago. Beautiful winter night in Chicago.

Like many midwestern states, Chicago tends to be gloomy for half the year. For much of the winter, it’s brutally cold, snowy, and icy. The cloud cover can undoubtedly dampen one’s spirits if they’re looking for sunshine and warmth.

Not all hope is lost, though. If you want to visit Chicago but avoid the cold, the summer is an excellent time to go.

Lots of traffic, always

Traffic in downtown Chicago with people, train, car and bus

If sitting in heavy traffic isn’t your cup of tea, Chicago may not be for you. It can easily take 30 minutes to travel the span of a mile due to the congestion mixed with never-ending traffic lights.

Because of this, drivers can get a bit aggressive, and you’ll hear car horns at every turn. My taxi driver blared his horn at least three times while I was in his car.

It can be expensive

From parking to transportation to tourist attractions, nothing in Chicago comes cheap. The hotel I stayed at charged upwards of $40 per night just to park there. Taxis cost more than expected to travel a short distance. Most of the activities that people visit Chicago to do and see cost quite a bit.

However, there are a few things worth checking out that are free. Most of the free activities involve walking, so you’ll want to pack a good pair of shoes.

Why Chicago is worth visiting

1. Some of the most well-known food around

Deep Dish Chicago Style Pizza

Nearly everyone has heard of Chicago-style pizza and Chicago-style hot dogs. Chicago prides itself on having the ‘best’ pizza, hot dogs, and Italian beef.

Chicago-style pizza is deep-dish and fully loaded. With toppings, cheese, and sauce, one slice is enough to fill you. It is hearty, comforting, and absolutely delicious! I tried Giordano’s when in Chicago and was genuinely impressed.

Chicago-style hot dogs are another must-try. Whatever you do, just don’t request ketchup! It’s almost an insult.

On that note, the Italian beef sandwiches from Portillo’s are amazing! When living in Ohio, my husband and I once traveled 6 hours each way just to get an Italian beef sandwich with dipping gravy. It was 12 hours in the car for 30 minutes of food-coma goodness! It was a long day but so very worth it. When you try one, you’ll understand.

2. Plenty to see without spending a penny

Chicago skyline with skyscrapers and Buckingham fountain in Grant Park at dusk lit by colorful lights.

Chicago is a magnificent city to see if you’re up for some walking. With many parks and trails offering scenic skyline views, you’ll see just why it’s often voted one of the most beautiful cities in the United States.

Buckingham Fountain is a popular destination within the city. While it is captivating to watch at any time, nighttime is the best time to visit. As the sun goes down, Buckingham Fountain offers light, and music shows every hour. The water reaches up to 150 feet, which is quite impressive.

The Lakefront Trail is an 18.5 miles-long path that connects the four lakefront parks of Chicago. You can walk, run, bike, and skateboard, making it perfect for nearly everyone. Plus, you’ll be treated to the stunning views of Chicago.

The Lakefront Trail was one of my favorite things when I visited. I walked for miles taking in the views without realizing how far I’d gone.

3. Plenty of iconic architecture

Willis Tower

Did you know that the skyscraper was invented in Chicago? This has made an eternal impression in the world of architecture. With many iconic buildings to see, it’s easy to understand why people visit Chicago for the structures and their histories.

One such building is the Willis Tower, formerly known as Sears Tower. At one point, the Willis Tower was the tallest building in the world.

If you’re feeling brave, take a trip up to the Skydeck on the 103rd floor. The glass ledge gives you breathtaking views spanning four states in perfect conditions. I can attest that while a bit heart-stopping, the Skydeck is a thrilling experience.

Another notable architectural mention is Aqua, a hotel resembling a waterfall. Then there is Tribune, which features parts of some of the most famous structures across the world.

4. Some of the best museums in the world

The Field Museum is located on Lake Shore Drive next to Lake Michigan, part of a scenic complex the Museum Campus, Chicago, Illinois, USA
Editorial credit: Vlad G /

Chicago is home to 67 museums. From world-class art to anthropological collections, the art scene has something for everyone. With so many museums to choose from, it’ll be difficult to decide which ones make your must-see list.

The largest and most complete Tyrannosaurus Rex can be seen at The Field Museum. There’s also the Chicago History Museum, which honors the city’s past through interactive exhibits.

While checking out museums, don’t skip the Museum of Contemporary Art. This impressive museum is among the world’s largest museums that house art post-1950.

5. Legendary sports teams

The famous signage on a warm summer's night at Wrigley Field
Editorial credit: FiledIMAGE /

Chicago is home to some of the most iconic sports teams in the country. When people think of The Windy City, sports are towards the top of the list.

Visitors from near and afar visit the city just to catch a game at one of the famous stadiums (Wrigley Field) or a local bar. The energy is contagious whether you’re a sports fan or not.

Amongst the notorious teams are the Bulls, Bears, Blackhawks, Sox, and Cubs.

6. The locals are welcoming

People enjoying live concert at city park in Chicago
Editorial credit: msubhadeep /

I’ve visited a few destinations where the locals were rude and ignored any questions that came their way. Chicago isn’t like that. The locals are overall amiable and want to make your visit enjoyable.

If you ask where the best place to eat or the best attraction to visit is, you’ll get 100 different answers. However, they will give them with passion and pride for their city.

Strike up a conversation, and you never know what tidbits and secret gems you may discover!

7. The theatre scene

Chicago Theatre

If you love theatre, Chicago is definitely a place worth visiting. You won’t be short on options with 200 companies, both small and large, showing as many as 100 shows per night.

Chicago has one of the most abundant theatre scenes in the United States and is where many productions began before transferring to Broadway. These include Wicked, To Kill a Mockingbird, and The Devil Wears Prada.

Amongst the most famous theatres is the Chicago Theatre, which showcases plays, comedy, concerts, and magic. As you can see, Chicago’s live entertainment is at every turn.

8. Some of the best shopping around

The Magnificent Mile with lots of tulips planted in the median and cars passing by.

If you want a truly impressive experience, Chicago’s Magnificent Mile is your stop! Located on Michigan Avenue, you’ll be treated to luxury shops, upscale restaurants, swanky hotels, and some of the highest fashion.

Even window-shopping while pretending to live the high life is fun in this world-known shopping district. To live in the area costs a pretty penny. It ranks as one of the most expensive neighborhoods in the United States.

If you’ve always wanted to try one of Chef Gordon Ramsay’s restaurants, Gordon Ramsay Burger is within walking distance of Magnificent Mile in the River North neighborhood. Be sure to make a reservation, as walk-ins aren’t guaranteed.

9. Chicago is very walkable

Chicago Skyline Reflected on the Lakefront Trail along Lake Michigan
Editorial credit: James Andrews1 /

Chicago has been rated as one of the most pedestrian-friendly cities globally. If you get a hotel within the city (or have a Lyft drop you off), you have plenty at your fingertips within walking distance.

There are parks, boulevards, and walkways connecting the city and almost everything you’ll want to see within. There are lakefront paths that offer beautiful scenery as you take in Chicago.

When I visited, I stayed at a hotel within the city. I was within a mile of incredible restaurants, tourist attractions, and a tour trolley that took a tour throughout downtown. The only time I needed a taxi was when I wanted to go somewhere a little further out.

10. One of the best cities for blues

Blue Chicago Music Bar, Chicago, Illinois
Editorial credit: Joseph Sohm /

Chicago is the third blues capital of the world. Artists such as Muddy Waters and Buddy Guy made their name in the city. If you’re looking for some of the greatest blues clubs in the world, Chicago is the place to go.

The North River District is an optimal place for blues clubs and to learn the history of the music. Every June, the Chicago Blues Festival is held. The festival runs for three days, and you’ll get a chance to see some of the best blues musicians.

A fun fact is that Chicago Blues has had a heavy influence on early and even modern rock music.


So, is Chicago worth visiting? After listing ten reasons, you can surely see it is a definite yes! Chicago is accommodating, easy to navigate, and a city that has something for everybody.

While I am not sure when I’ll get to visit again, I do have a list of things I’d like to see next time around. Checking out Gordon Ramsay Burger is on the top of that list! If you happen to make it before I do, be sure to comment on your experience.

While Chicago might not have great weather year-round, there are still plenty of months to give you a fantastic trip. Just a heads up…the Lakefront Trail is absolutely stunning in the springtime.

2 thoughts on “Is Chicago Worth Visiting? 10 Reasons That’s a Yes”

  1. Question: We are 2 youthful Senior’s ages 74& 73 wanting to come by passenger train from Red Wing MN to Chicago for the first time. Where do we get off & get on to return? Does it go all the way downtown & if so, are their any good Blues Clubs in the immediate walking area that would be safe to walk back to at night? What hotels, Blues Clubs, Eateries would you recommend close to the Train Station?

  2. Excellent review of Chicago. I want to visit it (from UK) because it’s not only the blues city, but also the birthplace of what was to become house music (very popular in Europe and UK). Chicago and Detroit (for the techno, another form of house music). Cold weather doesn’t bother me, I’m Scottish. I love the sound of the lakefront walk and I love walking around cities, Edinburgh and Glasgow are very walkable, too. I want to check out the architecture and feel Chicago makes a change from the more obvious tourist destinations of L.A. and Vegas. I have, of course, been to New York.


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