It’s tricky to really capture the essence of Chicago if you’ve never been there. It’s so much more than deep-dish pizza and Navy Pier. In fact, it’s a little bit of a Gemini, like me: a pretty city and a gritty city. Sophisticated yet swaggering. Bold and beautiful. (Wait, that’s a soap opera.) Most people know the Magnificent Mile, but they’ve only met one half of this dynamic urban apex spiraling up from the ordinary heartland.
But I lived there for three years, so I had ample time to discover things to do in Chicago like a local. Let me introduce you to another side of Chicago.
First, you’ll find that people like to say they’re from Chicago when they really mean Schaumburg or some other suburb miles and miles down an interstate. It may be connected by urban sprawl, but it’s not Chicago.
At the same time, Chicago is a city of neighborhoods. Not subdivisions, but neighborhoods with personalities all their own. Some are cultural personalities: Andersonville is Swedish, Devon Avenue is Indian, Avondale is Polish, Chinatown is Chinese (of course). Some are social personalities: Wicker Park is grungy artist, Roscoe Village is granola mom, Streeterville is wealthy matron. You’ll find all kinds of people in all kinds of neighborhoods, but these are the pervasive vibes, reflected in the food, the religious structures and the shopping.
It is a gorgeous patchwork of diversity.
Sometimes it all comes together on the L, the elevated (and sometimes underground) train system that is the sole source of transportation for many urban dwellers. It’s a cacophony of languages and clothing styles. If you enjoy surreptitious people watching, riding the L is never boring.
I highly encourage people to take the L into Chicago’s various neighborhoods to explore. Go during the day — the unexperienced can easily wander into sketchy territory without realizing it. Chicago is a big city, third largest in the country (and only behind Los Angeles because that city includes its sprawling ’burbs). You have to be smart, friends.
Things to Do in Chicago
Start downtown at the Cultural Center, where you’ll find free brochures and maps for everything. Check the website in advance and you might be able to catch one of the free musical performances and shows always going on, or join in one of the free tours of the breathtaking building.
If you’d like a guide, book a free walk-around with a Chicago Greeter. These are tours by volunteers who love the city. You can schedule tours of 25 neighborhoods in Chicago, or explore topics such as the Great Chicago Fire, speakeasies, theaters…whatever floats your boat.
Speaking of boats: Did you realize that Chicago has beaches? And boats? And boat tours? It’s hard most days to see a horizon on Lake Michigan. You could be at the ocean for all you know.
If you want to sit in the sand with a beverage and listen to the waves or play some beach volleyball while toned young people meet up, North Avenue Beach is the place to be (and be seen).
If you want to see Chicago’s famous skyline from the water, book a trip on the Tall Ship Windy. Their pirate cruise with architectural notes is the perfect blend of corny and entertaining for adults as well as kids. (Bring a jacket for the breeze off the lake.)
And you can also explore Chicago’s famous architecture with a cruise down the Chicago River. The guides’ expertise is worth every single penny.
The titans of industry who developed the city’s architecture and plan are a part of the character of Chicago. If you’ve ever read Devil in the White City, you’ll have an appreciation for these can-do engineers who worked miracles without modern tools in the late 1800s. That scrappy, larger-than-life, against-the-odds mentality is probably the most pervasive characteristic that unites Chicagoans, whatever their neighborhood.
In essence, Chicago has heart.
But don’t forget that Gemini personality. It’s rough-and tumble for sure (just visit an Irish bar on St. Patrick’s Day), but it’s also one of the best restaurant cities on the planet, with internationally known chefs such as Stephanie Izard, Rick Bayless and Grant Achatz, one of the world’s culinary geniuses.
Broadway shows spend time in the glorious historic theaters of Chicago. And yet the performance landscape is equally known for bawdy Second City, launching ground of Dan Aykroyd, John Belushi, Tina Fey and most every other great American comedian. And there are hundreds of storefront theaters in those neighborhoods that I mentioned, where you can BYOB and sit six feet from the actors.
There’s so much to see and do in Chicago that you can spend years exploring and never hit repeat. I did. My daughter and I lived in the North Central neighborhood just 1.5 miles west of Wrigley Field for three years, while I was a food and wine writer. I experienced life with street parking (or lack thereof), brutal winters and ridiculously expensive everything, but I would never take it back. We tried to do it all! Here are a few of our highlights:
Great Chicago Restaurants
I highly encourage you to take the car, a cab or a bus and the L and get out and about to restaurants beyond the Mag Mile. Kids are welcome most anywhere unless it actually says 21 and over. And many restaurants are BYOB. Of course, many restaurants come and go with lightning speed, but these favorites were still serving amazingness the last time I visited.
Quartino / downtown / fun atmosphere in a bustling area serving quartinos of wine. You will be bumping elbows on weekends, but it’s a great time.
Shaw’s Crab House for brunch / downtown / an amazing raw bar with oysters, etc., and a room devoted to desserts at brunch. A darker, boys’ club, steakhouse sort of feel.
Turquoise / Roscoe Village / Turkish, awesome lamachun and warm bread with dip, great service. A small restaurant with bright contemporary decor.
Bristol / Bucktown / sexy room, interesting small plates. Think exposed-brick loft.
Coast / Bucktown / another sexy room, BYOB, super sushi in a ‘hood replete with hipster shops. You will think you walked into a vodka commercial.
Tango Sur / Lakeview / BYOB Argentina steakhouse, you can cut the meat with a spoon. Style is kind of irrelevant. Dining on the patio is exceptional, and Southport features some great boutiques.
Piccolo Sogno / West Loop / amazing, amazing outdoor patio. Voted best in the city several times. The interior’s no slouch, either. Italian food, gracious service. Make reservations for the patio well in advance.
Things to See in Chicago
Art Institute of Chicago. Always amazing. The permanent collection includes Seurat, Toulouse-Lautrec, Goya, Rembrandt, Warhol, Koons, Pollock and other heavyweights. Plus mummies!
Museum of Contemporary Art. So airy it can brighten the dreariest Chicago day. The view of the lakeshore through the huge windows is as wonderful as the art. It’s one of the world’s largest contemporary art venues, with many interactive features and mobiles by my man Alexander Calder.
The Federal Reserve Bank of Chicago Money Museum. They give you an interesting (if somewhat worrisome) overview of our financial system, then turn you loose to look at lots of money without spending any. (Temporarily closed during the pandemic, so check the website before you go.)
Macy’s. Known as Marshall Field’s to the locals. Go to the service desk and ask for the MP3 tour, so you can get the scoop on the Tiffany, the clock, and all the history before shopping. They have discount coupons for visitors there, too.
InterContinental Hotel. Go to the concierge desk and ask whether they still offer an MP3 tour. Be sure to check out the historic pool. Then go to Eno on the first floor for the best flights ever of wine or bubbly or cheese or chocolate.
The Field Museum. Plan to spend a day or two. And don’t miss the Egyptian exhibit. The whole building is social studies and anthropology made super-cool. It’s also part of the history of the famed 1893 World’s Fair held in Chicago. (Devil in the White City is the most entertaining way to dive in.)
Millennium Park. Check out the bean. (Ok, Cloud Gate. Does anyone even know what I’m talking about when I use the proper name?) Walk through the Lurie Garden. Splash in the fountain…unless it’s winter, in which case you should go ice skating. See the huge changing faces on the screens.
Lincoln Park: One of my favorite things to do in Chicago: Get up Saturday morning for the Green City Farmer’s Market, one of the best in the country. Get there by 10 a.m. for the demos by the city’s best chefs. Go afterward to the free Lincoln Park Zoo. Don’t miss the gorillas. (Consider buying a bus pass and catch the bus up Michigan Avenue. It’s a short ride, far better than driving and parking.)
The L. Choose a route and ride around—the Red Line circles downtown and goes all the way up to Wrigley Field. Hop off there and see the famous stadium. Ride the L back downtown. A great way to see without having to navigate traffic. Need a boost of confidence? See our blog on using public transportation.
During the summer, there are neighborhood street festivals every weekend. Check metromix.com for locations and schedules.
Also during the summer there are free movies in the parks all over the city, free concerts at Millennium and Grant parks, free SummerDance fun… really, you can do a lot for free in Chicago. (I should know; I was b-r-o-k-e when we lived there.)
See the top of the Hancock Building for free by going up to the Signature Room for dessert. (You have to pay for dessert, of course.)
These are just the highlights. If you’re still looking for ideas for how to visit Chicago like a local, cruise around that room in the Cultural Center where I suggested you start. Or find a good dive bar and ask an actual local. You’ll get many passionate opinions. (It’s known as the Windy City not for the cold gusts but all the hot air.) And you’ll get some new friends. Shoot, you might decide to stay at the bar all afternoon. And that would be a good thing to do in Chicago, too.
Although we strive to provide the most current information, bars, restaurants and attractions mentioned may close at any time, operate with a limited menu or reduced hours, or have takeout options only. We recommend checking individual websites for operating hours, updates, and social distancing measures before visiting.
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