According to Frank Sinatra, everyone has the time of their life in Chicago. Whether you’re here for a long weekend or a lifetime, certain experiences characterize the city. Chicago’s food, lake, theater, and arts all contribute to the rich cultural tapestry and there are a number of iconic things to do and signature places to eat that are required to have the quintessential Windy City experience. Here’s everything you need to have on your Chicago bucket list to get a full-picture of the magic toddling town.

Weigh in on Pizza Wars

Deep dish pizza is a way of life in Chicago with everyone having their favorite pie. Giordano’s (my go-to), Malnati’s, and Uno’s (the original) are generally the big three in the discussion which basically comes down to whether you prefer your ‘za saucier or cheesier. While no self-respecting Chicagoan will eat that heavy monstrosity all the time or we’d weigh 1000 pounds (thin crust from Piece is still the best), it’s a dish reserved for special occasions and wowing guests.

Photo Credit: Adam Alexander

Walk or Bike the Lakeshore Path

18-miles that spans the entire length of the city’s eastern boundary, you have to hit the lakefront to take in the grandeur of the Great Lakes. Plenty of friends have visited and commented it looks just like an ocean and were completely shocked when they realized you can’t see the other side.

portillo's hot dog

Try a Signature Chicago Dog

Another must-eat Chicago bucket list item, the city has more hot dog restaurants than McDonald’s, Wendy’s, and Burger King combined. And if you think you’ve had a hot dog before, think again. An all-beef frankfurter topped with mustard, relish, tomato, pickle, onions, celery salt (the secret ingredient), and sport peppers on a poppy seed bun, ketchup is a cardinal sin on this work of art. The best place to try it is Portillo’s, but for a more memorable dining experience, The Wiener’s Circle’s sassy and foul-mouthed employees just have to be experienced for yourself.

Find Your Favorite Museum

The dollhouses at the Museum of Science and Industry, the Andy Warhol exhibit at the Art Institute, the Caribbean Reef at the Shedd Aquarium, Sue the dinosaur at the Field Museum, and pondering the universe through space and time at the Adler Planetarium are just a few of the not to miss highlights of these world-renowned cultural institutions. (Pro Tip: save some money by snagging a CityPASS or discount card which allows you to visit multiple attractions at deeply discounted rates).

Photo Credit: Krista aka scaredykat on Flickr

Down an Italian Beef

The best homage to Chicago’s greasy mobster days, the Italian Beef is another sandwich the Windy City perfected. Thin slices of roast beef served topped with aus jus on a kaiser roll, you can order it dry (sans sauce), wet (topped with gravy, but not doused), or dipped (a submerged, soggy delicious mess) and topped with sweet or hot peppers, and cheese (generally mozzarella). Try one for yourself at Portillo’s or Al’s Italian Beef.

Photo Credit: City of Chicago

Attend a Festival

When everyone finally comes out of hibernation for the winter, Chicago’s festival season kicks off to celebrate what is arguably the best city in the world for three months of the year. The city pulls out all the stops with a different neighborhood street fest virtually every weekend from May through September. St. Patrick’s Day is our annual holiday where the river is dyed green, but Lollapalooza is also a major summer-must do.

Make it a Beach Day

There’s nothing like spiking the volleyball at North Avenue Beach, sipping on a pina colada at Castaways, and hopping on a friend’s boat to jet off to the Playpen to make you really appreciate the country’s third coast. The lake is such a part of life in Chicago that other Midwest cities get but coastal destinations find odd. Once you live there you see that lake life is just as awesome (and sometimes even better) than living by the ocean.

Catch a Game

A major baseball town, Wrigley Field is iconic, but Soldier Field is also one of the oldest football stadiums in the country. And there’s nothing more exciting than watching the puck fly across the ice at the United Center at a Blackhawk’s game, where you can also relive the Bull’s glory days from the Michael Jordan era.

Snap a Selfie

Did you really come to Chicago if you didn’t take a photo at the Bean (aka. Cloud Gate), Buckingham Fountain, or Millennium Park’s weird-faced water features? Spend some time wandering Grant Park, Maggie Daley Park (there’s an ice rink in winter), Lurie Garden, and the Jay Pritzker Pavilion soaking in the city’s best architecture and landscaping.

See the Skyline from Above

Head up to the 103rd floor of the Willis Tower Skydeck to lean out over the glass ledge, get your heart pumping at 360 Chicago where you can Tilt over the city, or enjoy a fancy drink at the Signature Room in the Hancock building to get a bird’s eye view of the skyline.

Take an Architecture Boat Tour

You saw the city from above, now see it from below. A river boat tour highlights over 40 landmarks and gives you a fascinating look into to the city’s growth by decade. Prefer to get a watery work out? You can also kayak the Chicago River for a self-guided tour.

Laugh it Up

Many of your favorite comedians (Bill Murray, Tina Fey, Steve Carell, and Chris Farley, to name a few) got their start at Second City, a world-renowned comedy club and improv school with nightly performances. But Chicago has dozens of places to get a laugh. Whether you prefer stand-up, sketch comedy, pros or up-and-comers, you could also check out the Laugh Factory, Zanies, and iO.

Visit one (or all) of the Food Neighborhoods

Craving ethnic cuisine? Chicago has it in spades. Take a trip to the Southside for Chinatown, the Westside for Little Italy, Devon Ave. for Indian food, or Argyle St. for Vietnamese. Some personal favorites include Tank Noodle for pho, Piccolo Sogno for pasta, and Phoenix for dim sum, but you could literally eat at a different restaurant every night for a year and not even make a dent in the rich culinary landscape.

Photo Credit: Illinois Office of Tourism

Window Shop on Michigan Avenue

It’s not called the Magnificent Mile for nothing. Chicago’s most opulent shopping district, Michigan Avenue, adjacent to the Gold Coast, is where all the high-end designers reside. Essentially the pulse of the city, take in the sights and smells wandering around Water Tower Place, visit the largest Starbucks in the world, and snack on Garrett’s Popcorn, another signature Chicago treat (the caramel/cheese mix is the best). For a more affordable shopping option, Akira in Wicker Park is a celebrated local label, which is where many of the independent boutiques can be found.

Eat at One of the Michelin-Starred Restaurants

Unequivocally one of the best food cities in the world, Chicagoans love to eat. And while hole in the walls have their place and time, Chicago attracts celebrity chefs in droves. Home to 25 Michelin-starred restaurants, Alinea is the crème de la crème with an ever-changing new-age molecular gastronomy tasting menu featuring imaginative, whimsical dishes like edible balloons crafted by a chef with tongue cancer who can barely taste. They also pioneered the ticketing system used by many high-end restaurants to pre-sell dinner seats like experiential theater. Tickets are priced on a sliding scale based on their date/time so once you’re at the restaurant, all you have to worry about is enjoying the food instead of the bill.

See the Animals

One of the oldest zoos in the country and one of the only with free admission, Lincoln Park Zoo is a 35-acre wildlife park with over 1,000 animals just north of downtown. Peruse the primates and mammals and take in epic views of the city from the unique walkway bridges and archways.

Photo Credit: Dice Sales

Get a Musical Education

The birthplace of blues and a hotbed of jazz, hit up one of the iconic clubs like the Green Mill, Kingston Mines, or Buddy Guy’s. With swinging nightly performances and jam sessions, get your groove on at one of these Windy City’s classic institutions.

Photo Credit: Dice Sales

Run or Bike the 606

Chicago’s answer to the Highline in New York, the 606 is Chicago’s new elevated trail. Running east to west, it offers a great view of Chicago’s diverse neighborhoods including Wicker Park, Bucktown, Humboldt Park, and Logan Square.

Act Like a Kid at Navy Pier

Designed by the same architect as the World’s Fair, Navy Pier is the Midwest’s #1 tourist attraction. Ride the ferris wheel for epic views of the city, play arcade games, get cultured at Shakespeare Theater, or go for a scenic dinner cruise along the lake.

Drink in the Rooftop Views

The Chicago Athletic Association, Virgin Hotels, Hotel Lincoln, and ROOF on theWit are just a few of the glorious hotels offering epic skyline views and even stronger cocktails with popular rooftop bars. Many even have retractable roofs or floor-to-ceiling windows to combat the winter chill while letting you hobnob in style.

Ride the “L”

Short for elevated despite being partially underground, the color-coded “L” train is the easiest and most efficient way to get around and a cool way to experience Chicago like a local. With over 140 stations, you’re never more than a few blocks from a stop making it the second busiest mass transit system in the country after only the New York metro.

Drive Route 66

Did you know Chicago was famously the start to the most iconic road trip in America? You can drive the entire Illinois portion from Chicago to St. Louis or snap a photo at the start marker and visit some of the original eateries and institutions.

Plan Your Trip: Where to Stay in Chicago

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8 replies
  1. Anonymous
    Anonymous says:

    Yay! you wrote about my hometown! Great list for locals & visitors alike. I would add: if visiting in the summer, splurge on a fireworks cruise on Lake Michigan – it was a highlight for my kids. Amazing skyline views

    Reply
  2. Anonymous
    Anonymous says:

    There is so much to do in this beautiful city. I read of Chicago a while back and I added the city in my bucket list. The things that caught my eyes were a wander in Lincoln Park, walk along the Michigan, the view of the skyline and the Art museum! I am definitely parking this! Thanks

    Reply

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