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.

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.

The Chicago theater scene is alive and well with exciting productions on the playbill throughout the year. From spectacular blockbuster musicals downtown to fresh exciting works coming out of the Belmont Theater District, not to mention special events and insider backstage tours, the city is bursting with show-stopping performances and experiences. This season is certainly no exception, and here’s what’s happening around town. 

Dazzling Productions in The Theatre District

Look no further than the Loop to find an incredible lineup of shows in the Theater District. Broadway in Chicago, offers some of the best seats in the house, bringing entertaining musicals and riveting plays to several of the fine venues in the area. This summer, step inside the gorgeous James M. Nederlander Theatre on W. Randolph Street when the Tony Award-winning Andrew Lloyd Weber musical Cats keeps the “Memory” alive July 16-August 4, 2019. Nearby, the grand Cadillac Palace Theatre presents another classic with the epic French revolutionary saga Les Misérables July 9-27, 2019 and also welcomes the new touring production of The Band’s Visit September 3-15, 2019. Over at the CIBC Theatre, the insanely popular Hamilton will delight audiences through January 5, 2020, while the acclaimed Goodman Theatre brings the laughs with the musical comedy The Music Man June 29-August 11, 2019.

For theatergoers who are interested in getting a behind the scenes look of one of the city’s most famous landmarks, The Chicago Theatre Marquee Tour provides a fascinating glimpse into the history, architecture and memorable moments that have taken place here. Just look for the hard-not-to-miss CHICAGO sign that adorns the front of the building on N. State Street.

Entertaining Engagements

Theater fans have a lot to look forward in other parts of the city. Along with the North American premiere of Six, an energetic pop-style concert inspired by the doomed wives of King Henry VIII at its main performance space on Navy Pier, Chicago Shakespeare Theater is expanding its reach with The Comedy of Errors July 18-August 18 as part of the Chicago Shakespeare in the Parks program.

Not too far from downtown, the Belmont Theater District, which spans the Lakeview and Lakeview East neighborhoods, is a vibrant area with theaters, restaurants, and shops that also happens to hold the distinction of being Chicago’s largest theater district presenting more than 100 shows weekly. From the Alfred Hitchcock-inspired, full length improvised thriller Hitch*Cocktails to the Blue Man Group and everything in between, there is certainly a show worth seeing.

One event you won’t want to miss is the free Broadway in Chicago Summer Concert at Millennium Park on Monday, August 12, 2019. For one night only, theater’s brightest stars will take to the stage of the Jay Pritzker Pavilion to sing new and classic show tunes under the beautiful Chicago sky.

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.