You know they say that you haven’t been somewhere unless you take a selfie to document it, right? Well, Chicago has no shortage of photo-worthy places to strike a pose. From world-famous attractions to colorful street art and mouth-watering food, there are so many vibrant visuals that you won’t mind having on your camera roll. Here are a few places to visit that are Instagram-worthy—just don’t forget #Chicago so everyone can see!

Day or night, The Chicago Theatre downtown is hands-down a must for selfies. Why? Well, no need to tag your location with the bright red, six-foot marquee letting everyone know the location. Apart from making a good backdrop, the historic venue, which has been welcoming audiences since 1921, is a good place to watch a concert, standup comedy and other shows from some of the biggest names in show business.

Art lovers who want a shot with a Picasso should make their way to Daley Plaza. Unofficially known as “The Picasso,” the massive, untitled Cubist sculpture by the Spanish master adds an interesting aesthetic to any photograph. At Millennium Park, which happens to be the most visited destination in the Midwest, “Cloud Gate,” does exceptionally well, as the ultimate selfie-backdrop. The futuristic-looking shiny work of steel by British artist Anish Kapoor attracts plenty of photo-snappers keen on capturing the cool reflection of the cityscape.

Within walking distance, the Art Institute of Chicago is a prized place with two majestic lion sculptures always camera-ready. During the year, the two African lion sculptures are decked out to honor hometown teams as well as to get in the festive spirit for the holidays.

If it’s the Chicago skyline that you’re after, there is a great angle from the Adler Planetarium on Solidarity Drive close to the Shedd Aquarium, both part of the area known as Museum Campus. Along with the soaring skyscrapers, Lake Michigan is also visible from this vantage point.

Nothing shouts fun more than a cool pic with a Ferris wheel. Whether it’s standing below or sitting high above at nearly 200 feet, or even better with the fireworks bursting in the background, the Navy Pier Centennial Wheel has become a go-to for the perfect shot. Nostalgic baseball fans have Wrigley Field, the home of the Chicago Cubs, a popular destination for smiling sports fans since it first opened in 1914. Today, people love to stand right in front of the red and white marquee and snap a selfie to preserve their memories. 

 

Leisurely walking tours are nice and all, but some people want pure adventure. Thank goodness Chicago offers exhilarating experiences for those out there on the wilder side. Have a look at the activities that you’ll want to check off your bucket list the next time that you’re around. 

Imagine staring straight down from more than 1,000 feet above. Yikes! When the fear of heights is not an issue, give TILT 360 Chicago a try. Located on the 94th floor of 875 North Michigan Avenue, the former John Hancock building, this innovative thrill ride offers a new window to the city with a glass-enclosed steel platform that tilts groups of up to eight ever so slightly a little over the edge. It’s worth it with the amazing views of the Magnificent Mile and the skyline that you won’t quite experience anywhere else. 

Meanwhile, on the water, the Seadog Speed Boat takes passengers on a riveting ride complete with twists and turns at a super-fast pace. Also, when the cruise is not zipping away, the experience includes interesting narration about the great city that is Chicago. You should note that getting wet will probably not be super difficult during this 30-minute boat ride that certainly flies!

Now it’s possible to feel the rush of floating in the air without having to jump out of a plane at iFLY Chicago, an indoor skydiving experience at Lincoln Park. This adrenaline-rushing activity involves putting a flight suit and experiencing unforgettable body flight in a gravity-defying, vertical wind tunnel two times per visit. The activity is safe and ideal for people of all ages and fitness levels. Plus, it’s great for families and groups. 

It’s okay to humblebrag after touring downtown Chicago from a helicopter. Prime views are what to expect when you sign up for a private helicopter ride from Chicago Aerial Tours. After departing from the Vertiport Chicago Heliport terminal, you’ll get to view the famous skyline and lake from a bird’s eye perspective. Ready? 

A little on the tamer side is taking in the fireworks at Navy Pier from the comfort of your seat on the Centennial Wheel. These are not just regular fireworks, by the way. They are a colorful pyrotechnic show synchronized to music overlooking gorgeous Lake Michigan that takes place Wednesday through Sunday from Memorial to Labor Day. 

Listen up ghouls and gals, Halloween will soon be here, and there are quite a few ways to celebrate the occasion. Whether you want to dress up and show off your costume, check out something scary or go trick-or-treating, there is so much to do in Chicago all month long. So what will it be?

So Wild

Families looking for a safe alternative to trick-or-treating should head out to Lincoln Park Zoo for Spooky Zoo, taking place on Saturday, October 26, 2019. Part of the annual Fall Fest, the beloved tradition also offers other fun activities from animal enrichment experiences to a fun corn maze, and more. Older kids and grown-ups who want to learn about the zoo’s haunted history can take a thrilling tour if they dare on October 29 and 30. Led by author, podcaster, and host of Mysterious Chicago Tours, this fascinating, 75-minute walkabout reveals scary things that you probably didn’t know including its cemetery past.

Phantoms of the Opera

Don your finest costume and wear a mask for the lively Lyric Halloween Masquerade. Hosted by the Lyric Opera of Chicago, this annual affair returns for an epic night of music by DJ Metro, dancing, signature cocktails, and bites from local restaurants. Besides, it’s all for a good cause with proceeds benefiting the emerging operatic talent of The Patrick G. and Shirley W. Ryan Opera Center. It goes down on Saturday, October 26 from 8 p.m. until midnight, so be there!

Halloween Fun at Navy Pier

Of course, Chicago’s iconic destination, Navy Pier, has a few things going on in honor of Halloween. Trick-or-treaters should bring a big bag and stock up on candy courtesy of participating establishments from 2 to 6 p.m. on October 26, 27 and 31st. Meanwhile, the Haunted Maze, is bound to instill frights thanks to spine-tingling twists and turns featuring ghosts from the Capone era and other dark moments from the city’s history. New this year is Cosplay on the Pier: Halloween Fest 2019, featuring a designated cosplay photo area, costume contests, and more on Saturday, October 26, from 2 to 10 p.m. What are you going to wear?

Not for the Faint of Heart

Stories of paranormal sightings and other grisly tales are in store during the Chicago Hauntings: Original Ghost Bus Tour offered throughout the year, including on Halloween. Veteran paranormal researcher Ursula Bielski brings brave groups to notorious sites from unfortunate tragedies, including the Eastland disaster, the Iroquois Theater Fire, and the St. Valentine’s Day massacre to the Hull House, which inspired the chilling movie Rosemary’s Baby. Known as the “World-Famous Supernatural Excursion,” this 2.5 to 3-hour excursion may have you sleeping with the lights on after it’s all over.

Ah, October—it’s a fine time for folks to revel in sweater weather, head outdoors for pumpkin-related festivities, pop into a museum, and enjoy exciting events with friends and family around town. Good thing there is a lot is going on, so be sure to make some room on the calendar for these worthwhile pursuits happening this month. 

Hey, Pumpkin

This is the season for all things pumpkin—pies, lattes, Jack O’Lanterns, parties. So, if you’re in the mood for some pumpkin, get to Jack’s Pumpkin Pop-up pronto. The cool interactive experience on Goose Island in downtown Chicago has plenty of displays of the bright orange fruit plus a challenging corn maze, carnival games, music, food trucks, bars, and a lively celebration open to all ages through November 3.

The inaugural Pier Pumpkin Lights event at Navy Pier is sure to become another fall favorite with its colorful pumpkin installations perfect for viewing after dusk with themed creations such as the Juggernaut of Jack-o-Lanterns and Pumpkin Picasso. Running through November 2, the seasonal celebration is a free public program that also features glowing light displays and deals on food and drinks at participating establishments.

Exciting Exhibitions

For those who prefer to be indoors, nothing beats spending a few hours immersed in culture. At the Art Institute of Chicago through January 5, 2020, “Rubens, Rembrandt, and Drawing the Golden Age” showcases the pinnacle of artistic creation in the Netherlands during the 17th-century.

On the other end of the spectrum, “Andy Warhol – From A to B and Back Again,” opening on October 20, is the first major U.S. retrospective of the Pop Art genius’ work since 1989 and will feature more than 350 works spanning the course of his career, including brilliant paintings of the famous soup cans and celebrity portraits as well as drawings, sculpture, video, and archival elements.

Festival Circuit

Cinema buffs won’t want to miss the Chicago International Film Festival taking place October 16-27, 2019. Presented by Cinema Chicago, the festival features an exciting line-up of movies from around the world, along with special presentations of the most highly anticipated releases, and themed programs including Architecture x Design, Women in Cinema and Documentaries including a Closing Night screening of The Torch that shines the spotlight on local blues musician Buddy Guy, who be in attendance.

The free public festival OpenHouse Chicago returns October 19-20, 2019 and offers an excellent opportunity to get an intimate look at more than 350 buildings throughout the diverse neighborhoods around the city. Hosted by the Chicago Architecture Center, the event offers access to skyscrapers, mansions, theaters and exclusive clubs with fascinating tours and talks that you don’t want to miss.

As far a comedy is concerned, Chicago is known for bringing lots of laughs. From improv to sketch and stand up, the city has established itself as a top destination for humor, hands down. On any given night, you can take your pick of places to see up and coming performers or famous faces commanding the mic. So the next time you’re in the mood to LOL, make your way to one of these popular spots.

Fans of improv pretty much have a definite destination in mind when they’re in Chicago: 1515 North Well Street in Old Town. The venerable address is home to The Second City, the legendary club, theater and school of improvisation that has been entertaining crowds since 1959. Outrageous and spontaneous skits keep the crowds coming, and don’t be surprised if the talented people you see on stage become famous on Saturday Night Live and beyond. Bill Murray, Dan Akroyd, Chris Farley, Tina Fey, Steve Carell, and Stephen Colbert are all alumni.

If you can’t get enough improv, the iO Theater in Lincoln Park is also a good bet. Founded by legend Del Close and Charna Halpern, the shows are sure to make you chuckle, especially any that involve long-form, anything can happen zany scenes of brilliance known as the Harold. The theater has also had a fair share of well-known comedians hone their chops here, notably Mike Meyers, Vince Vaughn, Amy Poehler, Seth Meyers, Jason Sudeikis, and Cecily Strong, to name a few.

Those who prefer stand-up should look no further than the Laugh Factory, the Chicago outpost of the famous California comedy club. Its weekly Chicago’s Best Standup Show is a showcase of rising local talent, but the venue is also known for drawing in headliners such as Dave Chapelle, Tim Allen, Whitney Cummings, Chris D’Elia and Kevin Nealon on occasion.

For something for the entire family, The ComedySportz Theater offers all-ages entertainment in its comedy, sports, and game mashup that involves a bumbling referee overseeing a hilarious battle of the wits unfolding along with anything-goes audience suggestions.

Along with these clubs on the circuit, big-name comedians also take their acts to Chicago. In August, watch out for Ali Wong at The Chicago Theatre, Judah Friedlander at The Hideout and Jeremy Piven at the Vic Theatre; and Norm Macdonald and Marc Maron at the Vic in September.