Natalie Frank, a Ph.D. in Clinical Psychology, can frequently be found wandering around Chicago, sampling all it has to offer.

Are you planning a trip to Chicago this fall? With all the yearly events and festivals, It’s a great time of year to visit. No matter where in town you are staying, there is something to do. Do you want to go to an event or attraction not in walking distance? Try the subway or a bus, which serves the city of Chicago and 40 nearby communities, or hop on and off the trolley or double-decker bus to your heart’s content.

Whether you are visiting alone or with the family, you’ll never lack things to do once the weather starts to cool. In addition to the regular attractions that abound in Chicago, head out to some of these great yearly fall festivals for a chance to sip some cider, take a hayride or get lost in a corn maze.

2018 Dates for Events Listed

2018 Date Event Location September 8-9 Chicago Bourbon and Barbecue Fest Roscoe VIllage September 14-16 Riot Fest Douglas Park September 15 Harvest Day at Garfield Park Conservatory East Garfield Park September 20 Adler After Dark South Loop September 20 Haute Dog Chicago River North September 22 National Museum Day Citywide September 22-23 Chicago Food Truck Festival North Park September 26-30 Chicago Gourmet Downtown September 7-23 World Music Festival Chicago Citywide October 7 (Other events on October 6) Bank of America Chicago Marathon Grant Park October 14 Bloody Mary Fest Fullerton October 13-14 Chicago Architecture Center’s Open House Citywide October 18 Adults Night Out at the Zoo Lincoln Park October 18 Adler After Dark South Loop October 20 Arts in the Dark Downtown October 15-21 Chicago Ideas Week Citywide October 18-28 Chicago Festival of Israeli Cinema Citywide October 27 - November 11 Chicago Humanities Festival Citywide

Chicago Bourbon and Barbecue Fest

If you love the smokey taste of food and distilled spirits then this festival is for you. Usually held the first weekend of September, the Chicago Bourbon and Barbecue Fest boasts a large bourbon tasting pavilion and smoked meats from ten barbecue kitchens. In addition to these tasting options, there are two music stages, one with country bands and the other showcasing local tribute bands.

Bands that have performed at this festival include Zepband Kashmir, 97Nine, The Gingers, Whiskey Road and Six String Crossing. Artisan’s and other merchants will line the streets and there is a kids’ area with special kid- and family-friendly activities. There is a suggested $5 donation. Bourbon tastings occur throughout the festival with tickets for 12 tastes costing $25 and those for 24 tastes priced at $49.

Neighborhood: Roscoe Village

Address: 2000 W. Roscoe St. Chicago, IL 60618-6202

Find out more here.

Riot Fest

This festival, held on the second weekend of September, is a three-day music event which features rock, psychobilly, punk, emo, alternative rock, metalcore, indie pop, ska, and hip hop. The festival is famous for showcasing reunions, unannounced guest performances, and complete album performances. Tickets start at $55 for one day. Bands that have played past festivals include The Cure, Fall Out Boy, Rise Again, Blink-182, The Misfits and No Doubt.

Neighborhood: Douglas Park

Address: 1401 S Sacramento Dr, Chicago, IL 60623

See the Official Website for more information.

Blink-182 plays Riot Fest Chicao

Harvest Day at Garfield Park Conservatory

This festival lets you learn about sustainable farming in the area as farmers help you learn about beekeeping, how goats and chickens are cared for, making compost and the techniques used to harvest organic fruits and vegetables, all in an urban setting. Listen to live music, taste one of a variety of different types of homemade honey and try your skill at some lawn games or perhaps a round of veggie bingo. This festival is advertised as a celebration of urban pioneer living. Held the Second Saturday of September, there is a suggested donation of $5 per person, with children ages 3 and under free.

Tips: The festival runs from 12:00pm until 4:00pm, so it is a very short day. The first time I went was shortly after I moved to Chicago and so I was unaware of how long the lines would be for this event. I got there right around noon and they cut the line off before I got in, so make sure to arrive at least an hour early if you want to make sure you'll get in. It's also good to be able to get in as early as possible as there is a lot to see and do. Another thing I noticed the first year was they were checking IDs, so make sure to bring one with you when you go.

Neighborhood: East Garfield Park

Address: Garfield Park Conservatory. 300 N. Central Park Ave.

Online: garfieldconservatory.org

Adler After Dark

Chicago has numerous museums that are wonderful to experience during normal hours. But they also often have special events at different times of the year that allow you to have a special experience of the exhibits and programs. Adler Planetarium, the first planetarium in the U.S., is one of the most popular museums in Chicago. Similar to Adults Night at the Zoo, Adler After Dark is a unique night out for adults only and occurs every third Thursday of the month, so it repeats in October. For added fun, some people attend in costumes that are based on that month’s theme so if you plan on going be sure to check the theme in advance.

Themes change each month so if you come back to Chicago you can return to the Planetarium without ever having the same night twice. When I went the theme was "Science Scavenge Adult Quest". We were given an answer sheet when we arrived and had to search for displays which gave information and then asked a question to be answered on the sheet. Some of the questions involved how to dispose of waste in space, what meteors are made of, the name of the Mars rover, and the names of different space exploration vehicles on display.

Admission is $20 General Admission ($15 Adler members) in advance and $25 General Admission ($20 Adler members) at the door. For an additional $8 (everyone) you can tour the Doane Observatory, which houses the largest aperture telescope in the Chicago area allowing you to see celestial objects billions of miles away.

Tickets include:

Full access all exhibits and galleries

Unlimited sky shows in all three theaters

Special guests appearances and lectures

Hands-on educational programs

Live entertainment

Tips: Bring money as the gift shop is fabulous and they open it during the event and there may be special tables set up with other things for sale. The night I went, there was a table with gorgeous prints of space including planets, galaxies, space explorers in outer space, space walks, and space exploration vehicles such as rockets, shuttles and the Mars rover. It's a good idea to get tickets in advance. Not only will you save $5, but you will be able to enter without waiting in line. We didn't do this as we went last minute and regretted it. Even though we were able to see the exhibits in all the galleries, we didn't have time to take advantage of any of the extras like the Sky Shows or lectures.

Neighborhood: South Loop

Address: 1300 S. Lake Shore Drive, Chicago, IL

Read more here.

Chicago Gourmet

Held the last week of September, Chicago Gourmet celebrates Chicago food and music. This event was created by the Illinois Restaurant Association to recognize Chicago’s culinary culture and the creative style of the chefs, Master Sommeliers, and wine-, spirit-, and beer-makers who join in. It underscores Chicago’s place in the international culinary community. The festival is held at Millennium Park, Harris Theater and the Chicago Athletic Association Hotel. Tickets start at $195 and there are a variety of packages, including several travel packages which include accommodation.

Neighborhood: Downtown

Address: Millennium Park, Harris Theater and the Chicago Athletic Association Hotel

Learn more at Chicago Gourmet

World Music Festival Chicago

Occurring the second and third week of September, this free music festival is the biggest and longest running festival of international music in the U.S. The festival is produced by the City of Chicago and the Chicago Department of Cultural Affairs and Special Events. Presenting musical styles from around the world, this event goes on around the city in 20 venues with more than 60 artists originating from more than 25 countries. Some of the bands that have played in previous years include:

Sona Jobarteh (United Kingdom | Gambia)

Actores Alidos (Italy)

Juana Molina (Argentina)

Andreas Kapsalis (Chicago, IL)

Altan (Ireland)

Chéjere (Mexico)

Ceci Bastida (Tijuana Mexico | Los Angeles, CA)

Quique Escamilla (Toronto, Canada)

Orquesta Akokan (Cuba)

Rio Mira (Ecuador | Colombia)

Innov Gnawa (Morocco)

Lo Còr De La Plana (France)

Emilia Amper (Sweden)

Jupiter & Okwess (Congo)

Delgres (Guadeloupe)

Quantic (United Kingdom | New York, NY)

Neighborhood: City Wide

Address: City Wide

Find out more at WorldMusicFestivalChicago.org,

National Museum Day

National Museum Day is a one-day event held all over the country on the third Saturday of September. On this day, you can gain free general admission to museums and cultural institutions all over Chicago. Visitors can download one ticket good for two people. Participating Chicago-area museums include:

Museum of Science and Industry

The Art Institute of Chicago

Museum of Contemporary Art

Smart Museum of Art

Chicago History Museum

Chicago Children's Museum

Peggy Notebaert Nature Museum Adler Planetarium

Shedd Aquarium

The Field Museum

Museum of Science and Industry

The Art Institute of Chicago

Museum of Contemporary Art

Loyola University Museum of Art

DuSable Museum of African American History

McCormick Bridgehouse & Chicago River Museum

Midway Village Museum

Elmhurst History Museum

Midwest Museum of Natural History

Wilmette Historical Museum

Fischer Farm

Tips:

Take the time to plan your trip in advance and don't try to take in too many Museums during the day. I went with two friends and each of us had a particular museum we wanted to visit so we intended to go to all three. We rushed through the first two missing a lot of the exhibits. Although we had time left to make it to the third museum, by that point we were too exhausted and ended up going home.

If you plan to go to more than one, also make sure to plan out your travel route. It's best to use public transportation to avoid the stress of driving in Chicago traffic and parking headaches. Make sure to add extra time even if using the subway and bus system, as there are often delays for construction and you may have to transfer and walk to get to your destination.

The first museum we went to was the Shedd Aquarium which is one of the most popular and had a very long line. I was definitely glad I was wearing comfortable shoes. Be sure you have footwear that you can walk and stand in for a long period of time in case you run into a line or visit one of the larger museums. Nothing will ruin your experience faster than pain from pinched toes and blisters.

Keep in mind that many of these museums will search any bags you bring with you and most will not allow you to bring food or drinks in. In some museums, you will be required to check anything larger than a moderately sized purse, so leave whatever you don't absolutely need at home and downsize any bag you plan to bring with you.

Neighborhood: Citywide

Address: Citywide

For more information read here.

Chicago Food Truck Festival

The first Food Truck was a Chuck Wagon which was used to feed cowboys on long cattle drives in the mid-1800s. Now there are all types of Food Trucks, from the standard hot-dog stands to more specialty options selling such dishes as spinach pie, lobster rolls, crepes, falafel and even grilled tofu.

There’s no doubt that in the past decade, the offerings from Food Trucks have grown more varied and exciting, and nowhere are quality Food Trucks more plentiful than Chicago. This festival usually held the third weekend in September, celebrates this American tradition with more than 30 gourmet Food Trucks all gathered in the same place offering tantalizing options. There’s also a Sangria Garden, nonstop live music and games. Complete with shady trees, tents and furniture you won’t have to eat standing up and can seek shelter from the elements whenever you choose. Event admission is free

Neighborhood: North Park

Location: LaBagh Woods, Chicago, IL 60646

Learn more about the festival here.

Haute Dog Chicago

Held at the beautiful Peninsula, Haute Dog Chicago is a doggie runway fashion show that benefits Canine Companions for Independence, an organization that provides professionally trained assistance animals to children, adults and veterans with disabilities. Usually held the third Thursday of October, this event features cocktails, hors d’oeuvres, a fall fashion show dogs alongside their owners, a silent auction, a special speaker, and the chance to see some of the canine companion puppies and future service dogs.

Dogs and their owners are attired in some of the most chic fall couture supplied by boutiques in the area. The silent auction always includes a variety of items at a wide range of prices to fit everyone’s budget.

Neighborhood: River North

Address: 108 E Superior St. Chicago, IL 60611

Bank of America Chicago Marathon

Held the first Sunday of October, the Chicago Marathon is one of the most popular road races in the world. Traveling a 5K course, serious and everyday runners from all 50 states and over 100 countries, compete to cross the finish line in Grant Park. This is one of the most exciting times of the year to be in Chicago.

There are a number of other events that occur that weekend, including Abbott Health & Fitness Expo and a parallel 5K wheelchair race. A post-race party will be held from 9:30am to 4:00pm at Butler Field. There will be live music, food and beverages. Free massages for race participants will also be provided by over 200 students, faculty, and alumni from Chicago’s Cortiva Institute. If you aren’t a runner, you can still take part as a spectator.

The cost for U.S. residents including Puerto Rico or other U.S. territories is $195 and for non-U.S. residents: $220. While registration begins almost a year in advance, there are some limited spots still available.

Neighborhood: Grant Park

Address: Start Line - Starting line at Columbus Drive and Jackson Drive.

For application and other information, visit the Chicago Marathon website.

For runners and spectators alike, the Chicago Marathon is one of the most exciting events held in the city

Bloody Mary Fest

This festival celebrates the various and sundry forms of the classic drink the Bloody Mary. Held the second weekend of October, at the Theater on the Lake, this event is a competition where festival-goers sample cocktails from various establishments then vote for their favorite. There are also other special brunch-themed cocktails, craft beer and small brunch plates to enjoy. While you taste different cocktail and food offerings you can enjoy live music, stroll through the Artisan Market and play lawn games.

For $25 you can purchase a special ticket which includes:

One 45 minute yoga session

One Breakfast Drink

One Breakfast Item

Giveaways and samples contributed by the sponsors

Early access to the artisan market

The $35 General Admission ticket includes:

Access to, live music, artisan market vendors, lawn games and more.

Samples of all competitor’s Bloody Mary’s, specialty drink samples (craft beer, mimosas and more)

Sweet and savory brunch tastes

2 Full drinks

1 Voting ticket for People’s Choice Award

A $65 VIP ticket is also available which, in addition to everything above, includes:

Express entry

1 extra full drink

Private area with seating.

Special Bloody Mary Fest souvenir.

Some of the proceeds will go to K9 4Keeps.

Neighborhood: Fullerton

Address: 2401 N Lake Shore Dr., Chicago, IL 60614

For more information see the festival website.

Chicago Architecture Center’s Open House

Normally held the second weekend of October, the Chicago Architecture Center’s Open House lets you tour some of the most famous as well as some of the least known buildings in the state, for free. This event gives you the chance to get a behind-the-scenes glimpse at more than 250 architectural spaces that are rarely, and sometimes never, open to the public.

Tour mansions, theaters, private establishments, residences, offices, secret rooms, hotels, schools, restaurants along with a variety of manufacturing, cultural and government facilities around the city. The sites chosen for the festival are intended to represent the cultural diversity and history of Chicago, and the unique character of the more than 20 neighborhoods included. You plan your own itinerary based on your specific interests. Some of the sites included are:

Blackstone Hotel

Cliff Dwellings

City Hall

Chicago Tribune Freedom Center

Chicago Loop Synagogue

Foundation Room at House of Blues

Civic Opera Building

Gentleman's Cooperative and Penthouse

Gems World Academy

Joffrey Towers

Goodman Theatre

Hard Rock Hotel Chicago

Revival Food Hall at the National

Spertos Institute for Jewish Learning and Leadership

Tips: Again, planning is essential here as you can only visit so many locations in two days. Comfortable shoes are another must. I only had Sunday available so I planned on going to only two buildings. I started at the Chicago Loop Synagogue which had amazing stain glass artwork created by Abraham Rattner. Unfortunately, I didn't take my own advice and my planning left something to be desired regarding the second location which was the Joffrey Towers. Having read that you can watch the company rehearse through large glass windows and being an ex-dancer, I really wanted to see this. Unfortunately, I didn't think to look for a schedule and when I got there they were done for the day. I still enjoyed touring the building. The views were stunning and I did at least get to see two of the company's studios. But with a little planning, I might have had the chance to watch that actual company.

Neighborhood: City Wide

Address: City Wide

Visit Chicago Architecture Center for more information.

Visit the secret vault that once belonged to mobster Frank Nitti in the basement of Harry Caray's Steak House at the Chicago Architecture Center’s Open House

Chicago Festival of Israeli Cinema

The mission of the Chicago Festival of Israeli Cinema (CFIC) is to encourage an appreciation for Israeli culture in Chicago. There are also several outreach events that take place throughout the year. The films selected for inclusion are intended to portray a dimensional image of the people, culture and contemporary artistry of Israel to increase the relationship viewers have with the country, its land and its people.

Movies shown at previous festivals include A Quiet Heart, Dimona Twist, Past Live, Operation Wedding, The Women’s Balcony, Antenna, Harmonia, and Abuela. Tickets prices are similar to standard movie ticket prices.

Neighborhood: Citywide

Address: Citywide

Learn more about the festival here.

Adults Night Out at the Zoo

Usually held the third Thursday of October, this adult-only event gives you the opportunity to spend time at the zoo after closing hour. You can attend special animal talks and educational programs, entertainment, and cash bars throughout the park. Explore the animal exhibits as you sip beer or wine under the stars. Tickets are $15 ($12 for Lincoln Park Zoo members) and $20 at the door.

Neighborhood: Lincoln Park

Address: 2400 North Cannon Drive, Chicago IL 60614

See here for more information.

Arts in the Dark

This free event, held the third Saturday of October, is an enchanting night parade that celebrates Halloween as the "artist's holiday". The event brings together organizations like the Art Institute of Chicago, and Lookingglass Theatre Company, important programs like After School Matters and individual artists for a fun-filled family-friendly event. The centerpiece of this evening is the parade which includes special floats, puppetry and artistic performances that are extra dramatic for being set against the backdrop of Chicago’s skyline.

The Arts in the Dark parade takes place on Columbus Ave. traveling north from Balbo to Monroe.

Neighborhood: Downtown

Address/Parade Route: Columbus Ave. from Balboa to Monroe

Visit Arts in the Dark for more information.

Chicago Ideas Week

This week-long festival occurring the third week of October brings together more than 200 global innovators and influencers. Participants speak on numerous topics such as leadership, life’s lessons, technology, science, entertainment, sports and current events during more than 150 different programs.

Since it began Chicago Ideas Week has featured some of the most inspirational speakers of our generation. These have included President Bill Clinton, General Colin Powell, Martha Stewart, Deepak Chopra, Marilu Henner, Reverend Al Sharpton, George Lucas, Hillary Clinton, Sean Combs, Malcolm Gladwell, Sandra Day O’Connor, Buzz Aldrin, Mike Bloomberg, Donna Karan, Rep. John Lewis and many others.

Programs include 90-minute Talks and 60-minute Conversations as well as hands-on Labs which teach practical skills such as how to make a perfect pie with world-famous pie chefs or creating graffiti with renowned street artists. Tickets are $15. Events are held all over the city.

Neighborhood: Citywide

Address: Citywide

For more information see here.

Watch Tony Award Winning Director Kenny Leon and Actress, Director Felicia Rashad Conversation at Chicago Ideas

Chicago Humanities Festival

The Chicago Humanities Festival, held from the end of October through the beginning of November, prides itself on programming about ideas that matter and that helps participants see the world in a different way. The aim is to push the boundaries of contemporary thinking and culture to aid participants better understand what it is to be human.

In the words of the organizers, “The Chicago Humanities Festival connects people to the ideas that shape and define us and promotes the lifelong exploration of what it means to be human. The Chicago Humanities Festival envisions a city and society in which its members engage in thoughtful dialogue, explore a diversity of ideas, and come together to find positive solutions.”

The festival invites some of the world's most exciting thinkers, novelists, artists, archaeologists, theologians, poets, architects, policy makers, scholars, playwrights, historians, musicians and others to explore ideas within the framework of civic life. Participants can attend performances, screenings, exhibits, and discussions organized by different themes in politics, society arts, culture, technology, economy and science.

Members of the Chicago Humanities Festival can attend many events for free. Memberships cost from $100 to $5,000. Prices for the public start at $45. Students, teachers, groups and young professionals can purchase memberships for special reduced prices. Volunteers can attend for free.

Neighborhood: Citywide

Address: Citywide

For more information see the official website.

© 2018 Natalie Frank

Natalie Frank (author) from Chicago, IL on September 10, 2018:

I think we end up in places for certain reasons, whatever they may be, Glenn. Even in cases when maybe we don't like living somewhere I believe there is a purpose, something we are lacking or some kind of task was need to complete. Leaving somewhere you are happy to go somewhere you have already been and where you know you would be less happy doesn't seem like a great idea, especially if you have the options of staying where you are.

Glenn Stok from Long Island, NY on September 07, 2018:

That was back in 1974, Natalie. I lived on Elm Street. I was only there for a few months though, because Sears sent me back to New York to manage the diamond system on their Manhattan computer system. However, they closed the NY office in 1978 and gave me three offers to choose from, but they were all in Chicago again. I could have been back in the Sears Tower, but after working in NY several years I didn’t want to leave again, so I quit Sears.

I wonder what my life would have been like if I moved back to Chicago for good. I would have a whole different circle of friends, for one thing. Who knows what else would be different. You got me thinking about that now.

Natalie Frank (author) from Chicago, IL on September 06, 2018:

How long were you in Chicago, Glenn? I have never been to the Oak Street Beach but I live on another one up in the Northern Suburbs which is nice. Yes, there are tons of festival in the fall, and lots of other activities as well. Thanks for reading and for the comment.

Natalie Frank (author) from Chicago, IL on September 06, 2018:

Glad you liked the article and enjoyed your time in Chicago, Chris. What did you do in particular that you thought was fun?

Natalie Frank (author) from Chicago, IL on September 06, 2018:

Glad something caught your attention Liz. After living outside of D.C. for almost 10 years the idea of having to pay big bucks to get into museums really upset me. So the free museum days are particularly great for me!

Natalie Frank (author) from Chicago, IL on September 06, 2018:

Glad the article was of interest to you, Linda. There's lots going on all year round in Chicago but I think Fall's my favorite time except it means of course winter is coming!

Glenn Stok from Long Island, NY on August 31, 2018:

I really related to your article, Natalie, and found it very interesting because my first job after college in the 70s was with Sears as a systems analyst. I worked in the Sears Tower (I know it’s called the Willis Tower now) and lived a few blocks from Oak Street Beach.

It looks like a lot has changed in Chicago since then, and you covered the events and attractions very well.

I remember going to the Museum of Science and Industry and the Zoo in Lincoln Park.

I didn’t realize there are so many fall festivities these days. Sounds very enjoyable. You did a great job including all the pertinent details.

Chris Andrews from Ohio on August 27, 2018:

Nice reference for activities. We recently took our daughter and niece to Chicago for a weekend. Was fun and activity filled. Great article.

Liz Westwood from UK on August 27, 2018:

Great ideas of things to do in Chicago. I especially liked the idea of free museum entry.

Linda Crampton from British Columbia, Canada on August 26, 2018:

You've described several events that I'd love to attend. I think that music, museums, architecture, and humanities would be very interesting to explore. Fall sounds like a great time of year to visit Chicago.