Whether you are a true Chicagoan or just visiting for the attractions, there are several things you have to do to truly experience the city. From trying different, iconic foods to exploring parks and museums, these 16 experiences should be had by all.
Time’s a wastin’ and you ain’t getting any younger, so bump these attractions up on your bucket list and get busy living! Check it out:
- Catch a comedy act at The Second City
Facebook/The Second City A school of improvisation, this infamous comedy club is located at 1616 N Wells Street. Chicagoans enjoy roasts, holiday shows, improv shows, and more throughout the year. Though it’s tough to get in, classes are available, and there are also locations in Hollywood and Toronto. Comedy legends such as John Belushi, Stephen Colbert, Joan Rivers, and Tiny Fey studied here!
- Get down with the Blue Man Group
Flickr/Cliff Colors, lights, music, and hilarious visuals come together to create a show like nothing you’ve ever seen (or will see again). Three bald, blue men use audience engagement and “instruments” made from random objects to put on a show that engages all of the senses. Performances take place at the Briar Street Theatre at 3133 N Halsted Street, but you can also catch shows in New York, Las Vegas, Boston, Orlando, and Berlin.
- View the city from the Sears/Willis Tower Skydeck
Wikimedia Commons/Olga Bandelowa Whether you’re a Chicago native or just love to visit, you haven’t truly seen the city until you’ve seen it from 1,353 feet in the air. Boxed in on a glass ledge that stretches 4.3 feet out from the building on the 103rd floor, you will get a bird’s eye view of the city that just can’t be experienced anywhere else. It is located at 233 S Wacker Drive.
- Picnic at the Jay Pritzker Pavilion
Flickr/Teacher Traveler Part theatre, part artwork, this event space in Millennium Park (which is part of Grant Park) lies along the lake and is a popular spot for hangouts and lazy afternoons. Located at 201 E. Randolph Street, it typically houses music festivals, symphonies, yoga, and other excellent events and activities.
- Take a #beanselfie
Wikimedia Commons/Ken Lund While most Chicagoans will try to pass this off as just another tourist attraction, you can’t deny that Cloud Gate, aka “The Bean,” is an iconic structure that adds to Chicago’s unique character. No one can resist staring at themselves amongst the crowds as if they’re looking down from a cloud!
- Eat at Alinea
Facebook/Alinea With only 20 tables available, one of the world’s best restaurants is right here in Chicago. Guests must buy tickets months ahead of time for this full dining experience that is far more than just a meal.
Facebook/Alinea Visitors enjoy a tasting menu of many different types of unique and artfully crafted dishes. Dinners last several hours and can cost up to $1,000 for two, so this one is definitely worth saving up for a special occasion. The restaurant is located at 1723 N Halsted Street. Click here for more information.
- Eat a five pound burger
Facebook/Fatso’s Last Stand What began as a simple hot dog stand in the Ukrainian Village is now known for a wide variety of different delicious eats like fried shrimp and salami sandwiches. It uses mac and cheese as an ingredient and is home to one of the biggest burgers you can find! The restaurant is open late (until 4:00 a.m. on Fridays and Saturdays) and is located at 2258 W Chicago Avenue.
- Try a Chicago or Depression-style hot dog
Wikipedia/Arnold Gatilao A typical Chicago-style dog is served on a bun with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and celery salt. Depression dogs are very similar and just as delicious! There are many places to get them, but locals love Gene and Jude’s located at 2720 River Road in River Grove. Find where you can get this hot dog.
- Enjoy a slice of deep dish
Wikimedia Commons/4pf3154f7 Some may say it’s overrated, but that doesn’t make it any less delicious. Even if you prefer a stuffed or pan pizza, Chicago knows how to serve up a mind-blowing pie you’ll crave for weeks. We recommend Pequod’s or Lou Malnati’s.
- Catch a Cubs game
Wikimedia Commons/redlegsfan21 Wrigley Field gives you the classic baseball experience while also witnessing one of the most famous teams in the world play ball. The Cubs recently broke their famously long losing streak by winning the World Series in 2016 - their first championship win in 108 years! The Sox, the Bears, and the Black Hawks are definitely worth a see as well.
- Visit all three museums at Museum Campus
Wikipedia/David K. Staub Museum Campus is a 57-acre park that lies along Lake Michigan in downtown. It is home to The Field Museum, Shedd Aquarium, and Adler Planetarium and visiting all three in one day is known as the trifecta. It’s the perfect way to spend a day in the city!
- Swim in Lake Michigan
Wikimedia Commons/TonyTheTiger As Chicago is a coastal city, most of it lies along the lake. Natural and man-made beaches abound, giving locals plenty of space for building sand castles, sunbathing, and accessing the water. The lake is also great for fishing, boating, and water skiing.
- Walk the 606
Wikimedia Commons/Victor Grigas As part of a push for hundreds of new parks in Chicago, the old Bloomingdale Line was converted into a nature walk for locals of Logan Square, Wicker Park, Humbolt Park, Bucktown, and surrounding neighborhoods. Also known as The Bloomingdale Trail, it took about a decade to complete the project, which opened in 2013.
- Run the Chicago Marathon
Wikimedia Commons/TonyTheTiger It’s time to start training! Alongside the Boston Marathon, as well as those in New York City, London, Berlin, and Tokyo, our city is home to one the biggest running events outside the Olympics. It has taken place almost yearly since 1977, though the first marathon was held in 1908! The race allows 45,000 runners and gives participants 6.5 hours to complete (you can take longer but you won’t be timed). If running isn’t your thing, the marathon is still and excellently exciting event to attend - especially at the finish line!
- Visit ZooLights around the holidays
Flickr/Connie If you love holiday lights, then you simply must visit the Lincoln Park Zoo in December. It is free, open daily, and attracts hundreds of people to come see the dazzling display every day. For ZooLights, the whole park is filled with lights and music. The changing colors, moving formations, and light statues are sure to delight and astound!
- Christkindlmarket
Flickr/Doug Sun Beams Inspired by a German tradition dating back to 1545, this incredible annual market brings European holiday culture to the Windy City. Most come for the food, including the best hot chocolate in town, but there are also a plethora of vendors selling ornaments and other gifts of all types.
Hungry for more fun in the city? Check out these 10 pizza places in Chicago that are too good to be true.
Facebook/The Second City
A school of improvisation, this infamous comedy club is located at 1616 N Wells Street. Chicagoans enjoy roasts, holiday shows, improv shows, and more throughout the year. Though it’s tough to get in, classes are available, and there are also locations in Hollywood and Toronto. Comedy legends such as John Belushi, Stephen Colbert, Joan Rivers, and Tiny Fey studied here!
Flickr/Cliff
Colors, lights, music, and hilarious visuals come together to create a show like nothing you’ve ever seen (or will see again). Three bald, blue men use audience engagement and “instruments” made from random objects to put on a show that engages all of the senses. Performances take place at the Briar Street Theatre at 3133 N Halsted Street, but you can also catch shows in New York, Las Vegas, Boston, Orlando, and Berlin.
Wikimedia Commons/Olga Bandelowa
Whether you’re a Chicago native or just love to visit, you haven’t truly seen the city until you’ve seen it from 1,353 feet in the air. Boxed in on a glass ledge that stretches 4.3 feet out from the building on the 103rd floor, you will get a bird’s eye view of the city that just can’t be experienced anywhere else. It is located at 233 S Wacker Drive.
Flickr/Teacher Traveler
Part theatre, part artwork, this event space in Millennium Park (which is part of Grant Park) lies along the lake and is a popular spot for hangouts and lazy afternoons. Located at 201 E. Randolph Street, it typically houses music festivals, symphonies, yoga, and other excellent events and activities.
Wikimedia Commons/Ken Lund
While most Chicagoans will try to pass this off as just another tourist attraction, you can’t deny that Cloud Gate, aka “The Bean,” is an iconic structure that adds to Chicago’s unique character. No one can resist staring at themselves amongst the crowds as if they’re looking down from a cloud!
Facebook/Alinea
With only 20 tables available, one of the world’s best restaurants is right here in Chicago. Guests must buy tickets months ahead of time for this full dining experience that is far more than just a meal.
Visitors enjoy a tasting menu of many different types of unique and artfully crafted dishes. Dinners last several hours and can cost up to $1,000 for two, so this one is definitely worth saving up for a special occasion. The restaurant is located at 1723 N Halsted Street. Click here for more information.
Facebook/Fatso’s Last Stand
What began as a simple hot dog stand in the Ukrainian Village is now known for a wide variety of different delicious eats like fried shrimp and salami sandwiches. It uses mac and cheese as an ingredient and is home to one of the biggest burgers you can find! The restaurant is open late (until 4:00 a.m. on Fridays and Saturdays) and is located at 2258 W Chicago Avenue.
Wikipedia/Arnold Gatilao
A typical Chicago-style dog is served on a bun with yellow mustard, chopped white onions, sweet pickle relish, a dill pickle spear, tomato slices, pickled sport peppers, and celery salt. Depression dogs are very similar and just as delicious! There are many places to get them, but locals love Gene and Jude’s located at 2720 River Road in River Grove. Find where you can get this hot dog.
Wikimedia Commons/4pf3154f7
Some may say it’s overrated, but that doesn’t make it any less delicious. Even if you prefer a stuffed or pan pizza, Chicago knows how to serve up a mind-blowing pie you’ll crave for weeks. We recommend Pequod’s or Lou Malnati’s.
Wikimedia Commons/redlegsfan21
Wrigley Field gives you the classic baseball experience while also witnessing one of the most famous teams in the world play ball. The Cubs recently broke their famously long losing streak by winning the World Series in 2016 - their first championship win in 108 years! The Sox, the Bears, and the Black Hawks are definitely worth a see as well.
Wikipedia/David K. Staub
Museum Campus is a 57-acre park that lies along Lake Michigan in downtown. It is home to The Field Museum, Shedd Aquarium, and Adler Planetarium and visiting all three in one day is known as the trifecta. It’s the perfect way to spend a day in the city!
Wikimedia Commons/TonyTheTiger
As Chicago is a coastal city, most of it lies along the lake. Natural and man-made beaches abound, giving locals plenty of space for building sand castles, sunbathing, and accessing the water. The lake is also great for fishing, boating, and water skiing.
Wikimedia Commons/Victor Grigas
As part of a push for hundreds of new parks in Chicago, the old Bloomingdale Line was converted into a nature walk for locals of Logan Square, Wicker Park, Humbolt Park, Bucktown, and surrounding neighborhoods. Also known as The Bloomingdale Trail, it took about a decade to complete the project, which opened in 2013.
It’s time to start training! Alongside the Boston Marathon, as well as those in New York City, London, Berlin, and Tokyo, our city is home to one the biggest running events outside the Olympics. It has taken place almost yearly since 1977, though the first marathon was held in 1908! The race allows 45,000 runners and gives participants 6.5 hours to complete (you can take longer but you won’t be timed). If running isn’t your thing, the marathon is still and excellently exciting event to attend - especially at the finish line!
Flickr/Connie
If you love holiday lights, then you simply must visit the Lincoln Park Zoo in December. It is free, open daily, and attracts hundreds of people to come see the dazzling display every day. For ZooLights, the whole park is filled with lights and music. The changing colors, moving formations, and light statues are sure to delight and astound!
Flickr/Doug Sun Beams
Inspired by a German tradition dating back to 1545, this incredible annual market brings European holiday culture to the Windy City. Most come for the food, including the best hot chocolate in town, but there are also a plethora of vendors selling ornaments and other gifts of all types.
How many of these Chicago traditions have you completed? Share your experiences with us in the comments!
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