What makes a city a bucket list city? A number of factors go into that choice but the main idea is that the city needs to have world-class aspects that make it a fun, interesting, and incredibly memorable place to visit.

You need to have fantastic meals in a bucket list city. You need to find amazing entertainment, see great sites, take in great views, and have strong feelings evoked in a bucket list city. Bucket list cities are those that you should visit at least once in your life to experience the art, the culture, and the vibe to truly understand what makes the city great.

To have a robust travel portfolio, a few specific American cities ought to be on your bucket list. Experience the hustle and bustle of New York, the glitz and glamour of Los Angeles, and the overwhelming sights and sounds of New Orleans.

Chicago is a city that ranks right up there with these other cities as a “must experience” American city. The Windy City has so much to offer visitors and, once you go, you will understand what makes the city so great. Here are five reasons Chicago should be on your travel bucket list.

# You Are Guaranteed to Eat Well

When you visit Chicago, check out the local favorites. Everyone’s food bucket list should include Chicago deep dish pizza, Chicago dogs, and Italian beef. What makes Chicago a true bucket list city, though, is how far beyond these iconic foods the cuisine of the city goes.

In Chicago, you will find everything from fine dining to excellent neighborhood restaurants representing many diverse backgrounds. You can take a food tour of the world without ever leaving the Chicago area and find some of the best Mexican, Greek, Polish, Chinese, and Italian foods.

The neighborhoods in Chicago each have unique tastes and ambience. You can check out the trendy sports in the West Loop or River North neighborhoods or the cultural diversity in Pilsen. Rediscover comfort food classics in Lincoln Park or hit a hip café in Wicker Park or Bucktown.

You can’t leave Chicago without eating a meal from at least one of the city’s critically acclaimed restaurants from some of the best chefs in the world. Whether it is Stephanie Izard’s Girl & the Goat, Grant Achatz’s Alinea, or Rick Bayless’ Frontera Grill, these restaurants are among the best in the world and will give you a meal you won’t soon forget.

# It’s Surprisingly Romantic

The list of most romantic American cities often includes New York, Charleston, and San Francisco but Chicago is right at the top of that list, too. The city has a great deal to offer couples planning a romantic getaway. In addition to the romantic restaurants, beautiful hotels, and picturesque scenery – both natural and manmade – make for a perfect couples’ destination.

Chicago offers beautiful fountains and public sculptures as well as beaches and parks. You can stay in a quaint boutique hotel like the Publishing House Bed and Breakfast or a stunning old high-rise building like the Chicago Athletic Club. And, there is almost nothing more romantic than taking a stroll down the Chicago River at night while admiring the architecture.

If you’re thinking of using a Chicago trip as an excuse to get engaged, Party Slate’s list of the best places to propose in Chicago is a good place to start. The city offers a wide range of places to pop the question to your future spouse including rooftop bars with panoramic views, art museums, or even the historic Navy Pier.

# Incredible Views

Chicago Bridge
Grant Park, Chicago

One of the best ways to experience a bucket list city is to climb to one of the highest spots in the city and look out on its majesty. Chicago offers many great vantage points to get these views that will forever live in your memory (and on social media). You can also find spots to admire Lake Michigan, the Chicago River, or some of the architecture in the world-famous “Chicago School” style.

Willis Tower, once the tallest building in the world, has a sky deck perched over 1,300 feet in the air. For the daring, they even offer a glass-bottomed area called the Ledge you can walk out on and for that feeling of floating over the sprawling city below. The John Hancock Center also offers an observation deck and here, you get a 360-degree view of the City of Broad Shoulders.

A handful of great places offer food and drink with incredible views. You can grab a bite or a cocktail while admiring the lake from Navy Pier’s Riva Crabhouse, check out the river from River Roast, overlook Millennium Park from Cindy’s, or check out Wrigley Field while having a beer at Smoke Daddy. For an extra special lunch, you can look out over the whole city and the lake from The 95th in the John Hancock tower.

# You’ll Never Laugh Harder

“Live from New York…” are some of the most famous words in comedy, but do you know where many of the most famous cast members in Saturday Night Live history come from? Chicago, of course! The famed Second City improv group has been splitting Chicagoans’ sides since the 1950s but starting in the 1970s, it became the recruiting ground for Loren Michael’s new SNL program.

For the past 50 years, the show has remained an important part of American comedic culture and Second City has continued to provide the comedians that make the show go. From Bill Murray to Chris Farley to Tina Fey to Aidy Bryant and so many more, the Second City to SNL pipeline runs deep. You can still catch the latest rising stars perform improv at the Second City today and possibly see the next rising star before they hit studio 8H.

# It’s Easy to Get To

As the Jewel of the Midwest, Chicago sits in a great spot right in the middle of the country. No matter which corner of the U.S. you live in, Chicago will be one of the closest major cities to you. In addition to its convenient location, the city is one of the handful of U.S. cities that offers multiple airports. With thousands of flights a day going into both O’Hare and Midway airports, you can almost always get a direct, affordable flight which always makes a city a little more appealing.

# Conclusion

Bucket list cities need to have a little bit of everything. In Chicago, you get food, fun, romance, scenery, and it is easy to get to. What more can you ask? For these reasons and more, Chicago should earn a place at the top of your travel bucket list.


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