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.

Ready for a romance in Chicago? Whether you’re in a blossoming relationship, have been together for years or are just looking for something fun to do on a first date, the city is full of terrific activities just for two. Who knows—maybe experiencing these attractions together will spark even more attraction!

When you want an easy, breezy, casual activity, a twirl around the Navy Pier Centennial Wheel may be in order. Besides, no matter how many times you have been on this classic Ferris wheel, the surrounding scenery and skyline never get old. You’ll always have something interesting to talk about with that special someone when you’re taking in the views high above at 200 feet.

Another low-key but lovely activity is going on a bicycle tour. Bike and Roll is the spot for rentals since it’s located adjacent to the 18-mile bike trail along the western shore of Lake Michigan. You’ll be in sync as you ride in tandem and take in the surrounding sites including Buckingham Fountain and The Shedd Aquarium, Field Museum, Millennium Park, Lincoln Park, and its zoo, to name a few. Oh, and helmets and locks are included with all rentals.  

What better way to see if there are fireworks than aboard an Odyssey Chicago River Fireworks Cruise? The two-and-a-half hour experience is available Wednesdays and Saturday evenings through August 31, 2019. Along with dancing, a DJ and a delicious dinner, couples enjoy dazzling views of the fireworks show from Navy Pier. For those who prefer a daytime date, one of the lunch cruises is always an option.

Cocktails, conversation and paint night are in order at Bottle & Bottega Chicago Downtown. The BYOB studio regularly hosts themed events that will inspire you and your special someone to hone your inner artistes including the Tuesday Happy Hour, the Couples and BFFs Painting Party, and the Chicago Skyline Painting Party.

If you’re searching for something that stands out for a date, Adler After Dark at the Adler Planetarium will make quite the good impression. The experience is never the same as themes change monthly. The 21+ over event happens the third Thursday of every month from 6:30 p.m. to 10:30 p.m. May through August, and 6 p.m. to 10 p.m. the rest of the time. From walking hand-in-hand through the exhibition galleries to gazing at the sky shows, dancing, and having drinks, the evening offers so much possibility.

No visit to Chicago is complete without exploring the Magnificent Mile. While most people think of a 13-block stretch of North Michigan Avenue as the main thoroughfare, the reality is the Magnificent Mile District is actually larger and is bordered by Randolph Street to the south, North Avenue to the north, Lake Michigan to the east, and the Chicago River to the west. Within this vicinity, visitors will find some of the city’s legendary landmark buildings, buzz-worthy restaurants, world-class shops, hotels, cultural attractions, and so many interesting things to do.

Seeing the Sights

Travelers who want to learn more about the fascinating area and how it came to be the Magnificent Mile should join a guided tour to hear the stories, see the amazing architecture, and get the lay of the land. Big Bus Tours provides a great introduction with a hop-on and hop-off Classic Tour experience where guests learn how the area got its name as well as discover some of the thoroughfare’s most iconic buildings including the Historic Water Tower and Pumping Station, the only two structures in the area that are still standing after the Great Chicago Fire wreaked havoc on the city and the John Hancock Center (now renamed 875 North Michigan Avenue), which soars 100 stories and was the world’s second tallest building at its opening in 1968.

If you want a bird’s eye view of the Magnificent Mile and beyond, including Lake Michigan and four different states, the 360 Chicago Observation Deck in the iconic John Hancock building does not disappoint, especially if you’re brave enough to take a peek from TILT, an enclosed moving platform that tilts over Michigan Avenue from the 94th Floor.

For those who prefer exploring closer to the ground, the Magnificent Mile is also home to several cultural organizations. The Museum of Contemporary Art Chicago has an impressive collection of works and exciting exhibits such as its most current “Virgil Abloh: Figures of Speech,” which showcases the native Chicagoan and designer’s cutting-edge works including collaborations with another famous local, Kanye West, and Japanese artist Takashi Murakami through September 22, 2019. Meanwhile, the Chicago Sports Museum is a sports lover’s dream with high-tech, interactive installations that celebrate the city’s legacy in the world of sports. Of course, you can expect to see a lot of Chicago Bulls, Cubs and Bears memorabilia as well as fun exhibits including “Measure Up” where visitors get to test their skills against all-time greats such as #23 Michael Jordan.

Literary types will enjoy the lesser-known Newberry Library and its treasure trove of curious things such as the first edition of Alice and Wonderland, correspondence between Jack Kerouac and his publisher, among other rare items.

Finally, when retail therapy is in order, the Magnificent Mile is certainly the right place to go with three vertical malls, 900 North Michigan Shops, Water Tower Place and the Shops at North Bridge offering one-stop shopping and dining. Looking ahead, don’t miss the colorful store window displays, the Magnificent Mile Lights Festival and the Grand Tree Lighting Parade which kick off the holiday season in late November.

Summer is hardly over, and there are so many amazing things happening around Chicago this time of year. August is a busy month for sure with festivals and exciting events spanning arts, culture, food, and entertainment. Whether you’re in the mood to get your groove on, eat til your heart’s content or hop on a Segway and see the sights, here are some excellent options to check out in the weeks ahead. 

Segway Tour

Enjoy views of Chicago architecture and famous landmarks from a unique vantage point by signing up for one of the tours offered by Bike and Roll, located at the Navy Pier and Maggie Daley Park. A great intro to the city for those visiting in August is the Amazing Lakefront Tour highlighting DuSable Harbor and Park, Monroe Harbor, the Shedd Aquarium, Adler Planetarium, and Soldier Field, to name a few.

Chicago SummerDance

No need for a nightclub when you can just show off your moves during Chicago SummerDance, a free outdoor dance event series taking over city parks through August 24, 2019. Wednesdays through Sundays, the Spirit of the Music Garden in Grant Park and other Chicago Park District locations transform into a lively urban dance floor with complete with live bands, DJs and lessons in everything from Brazilian zouk to Ballroom, Salsa, House, and East Coast Swing. So get your dancing shoes on, grab some friends and don’t be shy because dancers of all levels are welcome. Oh, and for a few extra hours of dancing, be sure to come out for the SummerDance Celebration Grand Finale in Millennium Park on Saturday, August 24, from 1 to 8 p.m.

Grant Park Music Festival

Unwind and enjoy classical music concerts performed by a world-class orchestra, chorus, and special guests during the Grant Park Festival. The summer music series has been going on for many years and has become a beloved tradition for locals and visitors alike. August features a lovely line-up with the Grant Park Orchestra and violinist Vadim Gluzman performing Mozart’s Prague Orchestra at the Harris Theater for Music and Dance August 2-3 2019; the Mambo Kings on August 7 and Mahler’s monumental Resurrection Symphony featuring the Grant Park Orchestra and internationally renowned vocalists Amanda Majeski and J’Nai Bridges at the Jay Pritzker Pavilion.

Chicago Hot Dog Fest

It’s that time of year again when hundreds head to Lincoln Park at Stockton and LaSalle for the Chicago Hot Dog Fest presented by the Chicago History Museum. The picnic-style extravaganza goes down August 9-11, 2019 from 11 a.m. to 9 p.m. Friday and Saturday, and 11 a.m. to 8 p.m. on Sunday and will feature Vienna beef hot dogs prepared Chicago-style of course—and other ways, too. However, food isn’t the only thing on the menu with an exciting line-up of bands including the School of Rock, Bollywood Groove, Tributosaurus Becomes the Rolling Stones, to name a few, and fun family-friendly activities for all to enjoy. Don’t miss it!

Chicago Air & Water Show

Back by popular demand, the Chicago Air & Water Show presented by the City of Chicago and the largest free event of its kind in the country will return August 17-18, 2019. While the focal point happens above North Avenue Beach, people are still able to view all the action unfolding along the lakefront from Fullerton to Oak Street. This year’s performances include a lofty lineup such as the Royal Air Force Red Arrows, the U.S. Navy Blue Angels, the U.S. Army Parachute Team Golden Knights, the USMC Osprey Demo, among others.

Sangria Festival

The warm weather offers the perfect excuse to indulge in refreshing drinks from Spain during the Sangria Festival taking place August 17-18, 2019 at Humboldt Park. Art, music, and entertainment are all part of the festivities of this event that centers around hand-crafted cocktails from the city’s top mixologists. Other goodies include food stations serving small bites and more, and live music on the lawn from Spanish rock to reggae, salsa, and funk, as well as performances by flamenco dancers and more. Salud! Tickets start at $15.

As you can see, August is a fabulous time to get out and about in Chicago!