Is Chicago Worth Visiting? 7 Reasons To Visit In 2024
Are you trying to decide if Chicago is worth visiting?
Chicago is one of the most popular cities to visit for both U.S. and overseas visitors. But with other “big city” options like New York City and Los Angeles, what exactly is it that sets Chicago apart? Well, that’s a great question, and I’m here to help answer it!
I’ve visited the “Windy City” 6 different times and, for me, I love viewing the stunning architecture via a boat cruise, going to see a Broadway play, visiting museums, trying out new restaurants (the food scene is 10/10), and catching a Cubs baseball game.
And that only scratches the surface.
In this post, I’ll discuss all the reasons why Chicago should be on your travel list, plus examples of the best things to do while you’re here, where to stay, and insider tips.
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Is Chicago Worth Visiting?
Spoiler alert: Chicago is definitely worth visiting! The city offers a wide variety of attractions for all interests: Skyline full of skyscrapers? Check. Sporting events? Oh, yeah! Family-friendly activities? You bet. Theater? Uh-huh. Museums? Plenty. Beaches? Most definitely. Shopping? Absolutely.
If you’re visiting for just a day, a long weekend, or even a week or more, Chicago has so much to do and see to keep you entertained. As a bonus, it’s easy to navigate. Public transportation is straightforward, and the downtown area is very walkable.
It’s a special place that gives me the “warm fuzzies” for lack of a better term. Just play the popular song Chicago by Frank Sinatra and you’ll see what I mean.
Is Chicago Worth Visiting in Winter?
I’m not going to sugarcoat it — it gets pretty darn cold in Chicago during the winter months (January and February are the most brutal) with daily high temperatures hovering around 30–38°F. But it also means a low season for tourists, so you’ll find fewer crowds and the best prices on hotels.
If you are willing to brave the cold, there is plenty to do in Chicago in the winter. The city hosts the German-inspired Christmas market, Christkindlmarket, in November and December. There are also several outdoor ice skating rinks in Millennium Park and Maggie Daley Park and curling spaces (some even on hotel rooftops).
Additionally, Chicago’s Christmastime decorations are magical. Walk down Michigan Avenue or State Street for the best views! The winter season is also a great time to visit one of the world-class museums or take in a Broadway show.
But, in all honesty, if you can choose between summer and winter, I’d recommend visiting in the summer. However, if winter is your only option, don’t let that stop you from coming—especially if you can go in November or December.
7 Reasons Why Chicago Is Worth Visiting
There is much more to Chicago than just deep-dish pizza (don’t skip out on this though). Here are seven reasons why you should visit the “Windy City”!
1. Impressive architecture
The architecture in Chicago is second to none. The city is the birthplace of the first skyscraper and home to many other impressive buildings including John Hancock and Willis Tower (previously the Sears Tower) which were once the tallest in the world.
The best way to view these buildings and learn about the history that shaped the Chicago skyline, like the Chicago Fire of 1871, is by taking an architectural boat cruise on the Chicago River. HIGHLY RECOMMEND!
2. Deep-Dish Pizza. Need I Say more?
Deep-dish pizza is synonymous with Chicago and has become a huge part of its culture. Picture a pizza that’s about two inches tall, with layers of gooey cheese, hearty toppings, and rich tomato sauce stacked high within a buttery, golden crust.
Some of the most popular spots for deep-dish include Lou Malnati’s, Pequod’s (can take up to an hour to make, but worth it), Giordano’s, Gino’s East, Pizzeria Uno, and Pizzeria Due.
Or, for a slight variation on a deep-dish pizza, try the pizza pot pie at Chicago Pizza and Oven Grinder Co. TIP: You’ll need a knife and fork to eat this!
If you want to taste test a little bit of everything, book this highly-rated Chicago pizza tour which allows you to try different styles of pizza from deep dish to coal-fired to even tavern style (thin-crust). Believe it or not, according to GrubHub pizza deliveries, thin crust actually outsells the famous deep-dish style among Chicago locals.
3. Sports Galore
Chicago is one of eleven U.S. cities with teams in all five major American professional sports: baseball, football, basketball, hockey, and soccer. It has been named the “Best Sports City” several times for this very reason.
The city is home to not one, but two professional baseball teams, the Chicago Cubs and White Sox, Chicago Bears (NFL), Chicago Bulls (NBA), Chicago Sky (WNBA), Chicago Blackhawks (Hockey), and Chicago Fire FC (MLS). I mean, WOW!
In my opinion, nothing beats going to a Chicago Cubs game at the historic Wrigley Field on a nice summer day. The atmosphere is unmatched! For a unique experience, watch the game from one of the rooftops along Waveland and Sheffield avenues.
4. World-class museums
Chicago’s museums are a major reason to visit the city. I make it a point to visit a new museum every time I’m in the city, and I have yet to be disappointed.
The Art Institute of Chicago, one of the oldest and largest art museums in the United States, houses an incredible collection of artwork from around the world, including well-known pieces like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”
The Museum of Science and Industry offers interactive exhibits that make learning about science and technology fun and engaging for all ages.
Another must-visit is the Field Museum, home to Sue, the largest and most complete T. rex skeleton ever discovered. Plus, the Chicago History Museum and the DuSable Museum of African American History offer deep dives into the city’s rich and diverse heritage.
5. Lakefront and Beaches
As someone from a landlocked state with limited “water” options, I am in heaven every time I visit Chicago which has 24 sand beaches along the shores of Lake Michigan.
Admission to Chicago’s beaches is free (excluding parking fees). The beach season runs from the Friday before Memorial Day through Labor Day.
Several beaches including Ohio Street Beach, Oak Street Beach, North Ave Beach, Osterman Beach, and 57th Street Beach even offer chair and umbrella rentals. I recently visited North Ave Beach and spent $60 for two lounge chairs + umbrella combo (all-day rental).
6. Vibrant music and entertainment Scene
Arts, culture, Broadway musicals, comedy, music festivals — Chicago has it all!
The city hosts major music festivals like the Chicago Blues Festival, Chicago Jazz Festival, and Lollapalooza that attract people from all over the world. It’s home to iconic music venues like Green Mill, which Al Capone allegedly frequented often.
Chicago is also the theater capital of the U.S. and the birthplace of improv comedy, where stars like Bill Murray, Stephen Colbert, and Tina Fey got their start. Check out The Second City and Zanies Comedy Club.
Last, but certainly not least, you can enjoy new and long-running Broadway hits in the theater district located in The Loop (one of my favorite things to do).
7. A Ton Of Award-winning Restaurants
This is for all you foodies out there! Chicago consistently ranks among the top five cities in the United States with the most award-winning restaurants.
With more than 7,000 restaurants, including 7 AAA Diamond-rated restaurants, 25+ Michelin-starred restaurants, 40+ James Beard Award-winning restaurants, and even one restaurant that made it on the list for the top 100 restaurants on the planet (Smyth), you can eat like kings and queens while you’re here.
TIP: Enjoy top-tier dining at places like Oriole and Alinea, explore off-the-beaten-path options like El Ideas, Kasama, and Schwa, or choose more affordable spots like Galit and Sepia.
Is Chicago Safe To Visit?
Yes, Chicago is safe to visit, especially if you stick to the tourist areas. Neighborhoods that typically have higher safety ratings than others include Chicago Loop (downtown), Hyde Park, Lincoln Park, River North, Streeterville, West Loop, and Wicker Park.
Like any large city, it’s important to be aware of your surroundings and take common-sense precautions. I wouldn’t want you to accidentally get lost and find yourself in not-so-safe areas like Englewood, Garfield Park, Washington Park, Austin, South Shore, North Lawndale, Riverdale, and Grand Crossing.
Transportation Tip: Safety levels on the public transportation system (a.k.a the CTA or “L train”) can vary based on the time of day and day of the week. While no spot on a CTA train is perfectly safe, choosing a seat near the front, close to the conductor/engineer, and away from the doors is your best option.
FYI: The Red Line is considered the most dangerous (mainly at night). However, it’s pretty safe to take it to and from Cubs games (it’ll be packed with other fans).
Where To Stay
The best central location to stay in Chicago is on Michigan Avenue between Ohio Street and Jackson Boulevard which will put you within a 20-25 minute walk from the most popular sights. Here are a few recommendations on where to stay based on your budget:
Budget Option: Freehand Chicago
Located in a restored 1920s Art Deco building set in a prime location, this hotel offers both private and shared (dorm-style) rooms.
Mid-Range Option: theWit Chicago, a Hilton Hotel
Situated in central Chicago’s Theater District and steps away from a subway station, this 4-star hotel offers an on-site restaurant and rooftop lounge that was rated “hotel bar of the year”.
Luxury Option: The Langham Chicago
This classy and modern 5-star hotel is conveniently located in the River North neighborhood with an indoor swimming pool, award-winning spa, and incredible views of the city skyline, Chicago River, or Lake Michigan.
Looking for more options? Use the interactive map below to input your desired dates and verify availability for hotels and vacation home rentals.
FAQs
Have more questions? Search for your answer in the FAQ section below.
Is Chicago good for tourists?
Yes, Chicago is great for tourists with its many attractions, museums, parks, and incredible food scene. The city is known for being a smaller, less packed/busy version of New York. Especially during the summertime, there’s so much happening in Chicago with outdoor events, festivals, and baseball season, that you’ll easily be able to fill your schedule.
How many days in Chicago is enough?
Three to four days in Chicago is usually enough to see the main attractions and get a good feel for the city. If you have less time, don’t let that stop you from visiting. You can still do plenty — please see my guide for how to spend 1 day in Chicago.
Is Chicago walkable?
Chicago is extremely walkable and was even ranked the most walkable city in the U.S. for tourists by Travel + Leisure. When I visit, I stay in a central location (downtown, River North, or Streeterville) and walk everywhere. Most major sights are within a 20 to 25-minute walk.
Which month is best to visit Chicago?
It depends on what you like to do. For me, the best time to visit Chicago is during the summer (June to September). There are festivals and outdoor events nearly every weekend from Memorial Day through Labor Day.
Plus, the temperatures, though sometimes warm, are perfect for taking an architectural boat cruise and spending a day at the beach.
TIP: Summer is the peak tourist season in Chicago. Be sure to check for any major events during your planned visit, as they can impact hotel availability and prices.
Conclusion
For anyone on the fence about whether Chicago is worth visiting, I hope this post gives you a better idea about all the city has to offer. Whether you’re into arts, food, sports, or just exploring new cities, Chicago has it all.
My trips to the Windy City have always been memorable, and I can’t wait for my next adventure there. If you’re looking for a destination that “won’t let you down” as Frank Sinatra sang in My Kind of Town, Chicago should be at the top of your list.
