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.
But — for our visit — the most important thing is it isn't winter. The city comes alive in the summer, with street festivals and outdoor parties everywhere. "Summertime Chi" is one of the best places on Earth to eat, drink and enjoy.
Although Chicago is a clean, big American city, it isn't as easy to navigate as some other places. Please be sure to look around and limit walking while on your phone. The neighborhoods on this map are relatively touristy but be careful at night and at the music venues / bars after 10pm. Uber is the way to go to get around between neighborhoods that are too far to walk.
With that, here are a few ideas to spend a few hours taking in the city:
All recommended spots, pinned for you. Click a marker to learn more.
Chicago is known for its architecture. If the weather is nice, the best way to enjoy the views are from the lake and riverwalk.
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.
Continue off the lakefront trail onto the riverwalk for excellent views of downtown and plenty of stops to grab food, drinks or photos.
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.
Chicago's version of Central Park — a 100+ acre park that stretches up from North Avenue and Clark Street.
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.
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.
Classic Chicago architecture with ornate façade, original elevators, and extensive preservation. A landmark for Chicago School architecture.
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.
Classic American diner at the very end of Route 66 (a.k.a. Jackson Blvd — which goes all the way to L.A.).
A Chicago institution and well-renowned brunch restaurant.
Filipino-French café with the very best pastry in the city.
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.
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.
Famous for their "fancy" Miller High Life and other wild yeast beers.
Two Michelin star brew pub with one-of-a-kind beers.
More low key and in the hip Logan Square neighborhood.
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.
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.
Natural history museum with exceptional collection of gems and dinosaurs.
A nice aquarium with wonderful views of the lake.
Pop-up exhibits from Andy Warhol to local Columbia students.
Arguably the best blues club in America with both local and global acts.
Late night jazz club that once hosted Al Capone and other notable 1930s Chicago gangsters.
Hundreds of curated places to explore across Chicago — restaurants, bars, landmarks, and cultural gems.
Locations are plotted as they load. Use the filters below to narrow down by category and cuisine type.
The person behind this guide and why I love this city.
I've had the pleasure of hosting colleagues from around the world when they visit Chicago. Every time, I found myself sending the same list of recommendations — restaurants, neighborhoods, things to do. Eventually, I figured it was time to turn that list into something more permanent and shareable.
This site is a labor of love for the city I call home. Chicago doesn't always get the recognition it deserves compared to coastal cities, but anyone who spends real time here knows — there's no place quite like it. The food scene is world-class, the architecture is unmatched, and during the summer months, the energy is absolutely electric.
I hope this guide helps you make the most of your time in Chicago. Whether you're here for a few days or just passing through, there's something for everyone.
A note to our visitors: Welcome! I'm thrilled you're here. Please don't hesitate to reach out if you need any recommendations beyond what's on this site. Chicago is best experienced with a local's perspective, and I'm always happy to help.
Tips & Comments
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