Things To Do: 24 Hours in Chicago

Chicago. The Windy City. A changing landscape from winter to summer makes Chicago one of the most captivating cities to visit regardless of time of year. Rich with art and culture as well as a fantastic food and drink scene, the lakefront city has a lot to offer.

Getting into Chicago

Chicago’s airports are known to frequent travelers as the black hole of airports. Many road warriors refuse to fly through Chicago due to delays, but they are missing the chance to see a great city on layover. The airports are easily accessible to the city—hop an UberXUberXLUberBlack, or UberSelect into downtown to see the sights.

Where to Stay

There are plenty of great places to stay in Chicago. If you’re taking the high-end route, hit the The Langham Hotel there. For around $400 a night, you’ll get incredible views of the city, access to the private club at the top, and a luxury experience.

For something more affordable, check out the Kinzie Hotel downtown. The walls of the rooms have maps of the city and the simple décor and amenities help you save money. Rooms there go for around $150 per night.

Get a View of the City on a Nice Day

Once you’ve checked into your choice hotel, head over to the Willis (formerly the Sears) Tower for a great view of the city. The Willis Tower was once the tallest building in the Western Hemisphere at 1,450 feet tall. It is now out ranked by the new World Trade Center in New York City, but it’s still worth a trip to the top. The only caveat is that when the weather gets bad, you’ll only see the inside of a cloud. Check the weather for your 24-hour jaunt and get your $22 tickets online to save time.

If you don’t want to spend the cash for a view, head over to the Magnificent Mile and the Hancock Tower’s 96th-floor lounge, called the Signature Lounge. You’ll get a great view as well as some food and drink, if you are so inclined. After you’ve sipped a few libations, head back down to the street and shop the “Mag Mile” to your heart’s content.

If you happen to have a fear of heights but still want to check out the city itself, hop on the Brown Line—the elevated train makes a loop (hop off at Fullerton and get back on going the other way) around the city to get a good sense of what Chicago is all about.

Get Your Grub On

Chicago is known for its avant-garde food scene including molecular gastronomy and other trends. Check out the relatively new restaurant Grace, which has two Michelin stars for it’s rather creative use of foods like aged grits and kokum.

Chicago is also known for its BBQ and smoked meats. In that vein we recommend checking out Smalls and starting with the super creative brisket bibimbap. Oh, and the folks at Smalls deliver to Lizard’s Liquid Lounge, too.

Art and Aquariums

The Art Institute of Chicago has more than 300,000 artworks and artifacts from around the world. It’s worth a trip and a wander to see the fragments of buildings designed by Frank Lloyd Wright, as well as the Thorne Miniature Rooms.

A short Uber ride away from the Art Institute of Chicago is the Shedd Aquarium, a 75-year occupant of the Chicago Museum scene. There you can see a 100-year-old lungfish, some fascinating Amazon fishes, and some of the scariest predators in the sea. Entry is $54.95 for adults.

Do the Loop

Once you’ve wrapped up your art intake and seen life under the sea, hop an Uber to the North Loop and Millennium Park and start a free walking tour where you’ll see the Chicago Theater, Marshall Field’s (one of the first department stores), and again the Willis Tower. You’ll also wander by the famous Chicago Bean, aka Cloud Gate, in Millennium Park as well.

As your day ends it’s time to hit one of Chicago’s many well-known breweries and bars. We suggest heading over to Villain’s Black Market Craft for its gourmet burger and a pint of one of its rare brews.

If you’re looking for an old Al Capone haunt, check out the Green Mill, which was one of his favorites during the days of Prohibition. Dine above the secret underground tunnels where Capone cronies allegedly cut off the tongue of one of the lounge singers after he threatened to not play there anymore. Today the bar has a lively and fantastic jazz scene.

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