Welcome to Chicago

Good Pre-Reading: 36 Hours in Chicago

Chicago — a.k.a. the Second City, City of Big Shoulders, and Windy City — is located on the shore of Lake Michigan. It was incorporated in 1837 and grew rapidly in the mid-19th century. In 1871, the Great Chicago Fire destroyed several square miles and left much of the city homeless. After the fire, Chicago made noted contributions to urban planning and architecture, such as the Chicago School (i.e. Daniel Burnham), the development of the City Beautiful Movement, and the steel-framed skyscraper.

Today, the city remains one of the global hubs for architectural innovation including headquarters or major offices for architecture studios including SOM, Gensler, Studio Gang, SCB, JAHN, Gordin Gill, Perkins & Will, and many others. Chicago is an international hub for finance, culture, commerce, industry, education, technology, telecommunications, and transportation. It has the largest and most diverse derivatives market in the world, generating 20% of all volume in commodities and financial futures alone.

O'Hare International Airport is routinely ranked among the world's top six busiest airports by passenger traffic, and the region is also the nation's railroad hub (all three Class 1 railroads cross in Chicago). The Chicago area has one of the highest gross domestic products (GDP) of any urban region in the world, generating $700+ billion. Chicago's economy is diverse, with no single industry employing more than 14% of the workforce. The city is home to approximately 2.75 million people with 10 million in the surrounding region.

This website has two sections:

For out-of-towners staying in or near the Loop, I suggest picking a few items from the Home page. Stitch a few of these together for a perfect long weekend.
For those with more time, looking for something specific or live in town, check out the “More Attractions” page. I’ve lived in Chicago ~20 years and have made it my mission to find amazing dining and drinks across the city. I’ve assembled a list of over 500 recommended venues and will continue to refine the list to make navigation (and options) better.

With that, we welcome you to the best city in North America!

Interactive Map

All recommended spots, pinned for you. Click a marker to learn more.

See the City

Chicago is known for its architecture. If the weather is nice, the best way to enjoy the views are from the lake and riverwalk.

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Lakefront Park & Trail

The lakefront offers excellent views and a great place to run, bike or walk — especially in the mornings. Lake Michigan can look like a fresh-water ocean.

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Riverwalk

Continue off the lakefront trail onto the riverwalk for excellent views of downtown and plenty of stops to grab food, drinks or photos.

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Oak Street Beach

Chicago has a few beaches, with Oak Street being the closest to downtown. There is usually someone selling Mexican ice cream and treats — they are refreshing on hot days.

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Lincoln Park

Chicago's version of Central Park — a 100+ acre park that stretches up from North Avenue and Clark Street.

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Navy Pier

A tourist destination, but equally fun to see one of the world's first Ferris wheels, lake-bound boat tours, and other sights and sounds.

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Willis Tower

Tallest building in Chicago (and previously tallest in the world). The views from the top are quite good. The sushi in the food court is decent too.

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Rookery Building

Classic Chicago architecture with ornate façade, original elevators, and extensive preservation. A landmark for Chicago School architecture.

Food & Drink

Chicago is one of the best cities for food and dining in the U.S. Its restaurant scene has always incorporated local ingredients, refinement, and global influence. But it is also the city that holds junk food near-and-dear: hot dogs (Portillo's), Italian beef (Al's Italian Beef), deep dish pizza (Lou Malnati's), and sugary popcorn (Garrett's at the airport). Beer is sold everywhere too with local breweries earning plenty of accolades.

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Lou Mitchell's

Classic American diner at the very end of Route 66 (a.k.a. Jackson Blvd — which goes all the way to L.A.).

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Lula Café

A Chicago institution and well-renowned brunch restaurant.

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Kasama

Filipino-French café with the very best pastry in the city.

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Green Street Smoked Meats

Chicago is not well-known for BBQ, but Green Street is conveniently located in the West Loop. If you're keen to get American BBQ, try it here.

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Asadito

Chicago is home to one of the largest populations of native Mexicans and their descendants. Asadito is a variety restaurant with good tacos. For authentic Mexico City style carnitas, try Carnitas Uruapan in the Pilsen neighborhood.

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Off Color Brewing

Famous for their "fancy" Miller High Life and other wild yeast beers.

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Moody Tongue

Two Michelin star brew pub with one-of-a-kind beers.

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Hopewell Brewing

More low key and in the hip Logan Square neighborhood.

Culture & Landmarks

Chicago has long had a well-regarded arts scene, anchored by the School at the Art Institute of Chicago (SAIC alumni include Georgia O'Keeffe, Grant Wood, and Korean film director Sang-soo Hong). Blues music immigrated up the Mississippi watershed and called Chicago home with the last great Castle Records star — Buddy Guy — still playing at his nightclub in the South Loop.

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Art Institute of Chicago

Best collection of Impressionist, American, and Southeast Asian art in the U.S. If you go to just one museum in Chicago, this is the natural choice.

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Field Museum

Natural history museum with exceptional collection of gems and dinosaurs.

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Shedd Aquarium

A nice aquarium with wonderful views of the lake.

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Museum of Contemporary Art

Pop-up exhibits from Andy Warhol to local Columbia students.

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Buddy Guy's Legends

Arguably the best blues club in America with both local and global acts.

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Green Mill

Late night jazz club that once hosted Al Capone and other notable 1930s Chicago gangsters.