Chicago Traveler Blog

Chicago Traveler Blog

Fall Into Chicago Fall Festivals, Events and Halloween Madness! | Chicago Events October 2012

9/24/12 | by

Fall is a beautiful time of year in Chicago! The temperatures are just right (in the mid-60's, that's just right for this time of year) and there is still plenty of fun things to do in Chicago every weekend! Don't miss any chance to see the fall foliage in Chicago from one of the sightseeing cruises, or just exploring the city on your own!

From the Halloween happenings to the Fall festivals, concerts, Oktoberfests and more, every Chicago Traveler will be in for a busy vacation when they head to the Windy City this season! And yes, this time of year it is definitely the Windy City, so pack your sweaters and your camera and head to Chicago for some of the best things to do this fall!

Where are you going for Halloween? 

  • Lula Cafe - "The Violent Hour" - We don't have many details yet, but you can expect costumes, special, delicious drinks and a little bit of horror. 
  • Durbin's - Black and Boo Halloween Pawty - Sat, October 13 - Dinner, a premium open bar, raffles, door prices, a Halloween theme and DJ - $45
  • 27th Annual Revegners Halloween Party - Sat. October 27 - A costume contest, live music on 3 stages and an open bar.
  • Enclave - The House of Horrors - Sat. October 27 - Their 8th annual Halloween bash with drink specials. And ladies, we recommend that you stop by the male revue there beforehand. The Hunk-O-Mania show starts at 8pm and they've got the best Halloween costumes (or lack of) that you'll see all night!
  • UNCle Fatty's Rum Resort - Terror Island - Sat. October 27th - Their 5th annual Halloween Party with live music by the Spazmatics, a costume contest with a $500 prize and... well, do you need any more reasons to go? (No... you don't)
  • Tokio Pub's Halloween Bash - Sat. October 27th - $5 cover for dude, free for ladies - Live music by Ear Candy, themed drinks, and a midnight costume contest!
  • Stage Bar - The Halloween Party - Sat. October 27 - No cover to get in for live and DJ music, a costume contest with prizes and Halloween-themed festivities until  3am!
  • Mickey's Bar & Patio Monster Bash - Sat. October 27th - Halloween Party with drink specials until 3am!
  • Stout Barrel (Haunted) House and Galley - Sat. October 27th - A haunted house with drink specials, costume contests and more! 
  • Orso's Halloween Bash - Sat. October 27th - Costume contest, unlimited wine and beer (until 12am) and DJ Ruben Chilly is spinning all night!
  • Kit Kate Lounge and Supper Club - On Sat. October 27th they're having a 'Little Shop of Horros' Brunch and then on Sun. October 28th, they're putting on a Rocky Horror Halloween Brunch. Performances by Diva Madame X until 3pm.
  • Fizz Halloween Hell Raiser - Sat. October 27th - Dancing, drink specials and a costume contest.

Chicago Fall Festivals and Events

  • Chicago Marathon: October 7th celebrates one of the most popular marathons in the country!
  • Chicagoween: All of October - Enjoy the Halloween festivities all month long with costume contests, hay rides, pumpkin patches and more in Daley Plaza
  • Frankenplaza: The Daley Plaza gets extra spooky from October 28-30th!
  • Saturdays in October - Enjoy free tours of the Half Acre Beer Company after you RSVP. Tours are $10 cash, which gets you a pint glass and samples throughout the tour
  • The 51st annual Sycamore Pumpkin Festival in Downtown Chicago happens for a few days at the end of October 24-28. Food (and eating contests) giant pumpkin weigh0ins, a parade, craftshow, carnival and more are all here to celebrate the fall for 5 days! This years theme is: "happiness is... the perfect pumpkin."
  • Saturdays in October - Free admission to the Art Institute of Chicago from 5-8pm
  • Thursdays in October - Free admission to the Museum of Contemporary Art
  • Oktoberfest in Chicago happens at several venues throughout the fall! We'll keep you updated throughout the season on upcoming Oktoberfests - be sure to follow us on Facebook, Twitter and Google+ to keep up to date with all things Chicago!

Farmers Markets in Chicago Fall 2012
The Green City Market is a year round indoor market in Lincoln Park, but it's held outdoors through October. Stock up on all the local farmers product, meats, breads, cheeses and sweets before the outdoor market closes for the year!

Best Sightseeing Tours in Chicago Fall 2012
Chicago architecture tours are at their finest this time of year, especially the late afternoon/evening tours with beautiful views of the Chicago skyline when the seasons colors are at their finest! Check out some of the best tours of Chicago this fall for a great trip to see some of the best sights in Chicago, or to eat some of the best foods!

  • Chicago Food Tours: Eat your way through Chicago to help you stay warm for the winter! Some of our favorite food tours this fall include the Chicago Tastebud Food Tours and the Chicago Food Planet Tours. Both these tours walk you through some of the best neighborhoods, where you'll pass many of the top Chicago attractions which you'll want to go back for later, and stop at some of the best eateries in Chicago to get your hands on some delicious pizza, hot dogs, sweets and more!
  • Chicago Walking Tours: If you'd rather just walk and save the food times for later, take a strictly walking tour of Chicago and see the city from some of the most beautiful spots. These guided tours show you all the secrets and hidden gems of Chicago's architecture and history, as well as all the popular stuff too! Some of our favorites are Joyce Walks Chicago and Chicago Architecture Foundation Tours!
  • Chicago Boat Tours: Be sure to bring a sweater or light jacket this time of year, but definitely don't miss out completely on the boat tours in Chicago, because they're still up and running and some of the best sunsets of the year happen on these tours! Whether you're here to get a beautiful view of the Chicago skyline or to learn all about the Second City, this is our personal favorite way to do it! Book a Spirit of Chicago Tour or a Mystic Blue Chicago Tour for a great time, or any of our other favorite boat tours of Chicago this fall!

Best Places to Drink in Chicago This Fall

Many breweries release a pumpkin ale or Oktoberfest beer, something to celebrate the fall, and there are tons of places in Chicago to enjoy these craft beers! There are also great places to enjoy a drink or meal on an outdoor patio or rooftop deck in Chicago through the end of October!

  • Football fans be sure to check out the best sports bars in Chicago to find the bar that supports your favorite team (NFL or college) and drink with fellow fans, or just the bars that have the NFL Sunday ticket.
  • C-View of Affinia Hotel is a high class place for a meal with pretty reasonably priced drinks and light bar fare. Come pre- or post-dinner for a nice view and cocktail, or if you want to spend a little more enjoy your dinner here.
  • Roof at the Wit appeals to the trendy Chicago Travelers with fire pits and rooftop telescopes to stargaze as you potentially star-gaze among the clientele that hangs around here.
  • Rock Bottom is an elevated beer garden with tons of great beers and a patio with a fun atmosphere.

Chicago is one of the best places to be in the fall - the crowds have died down a bit, but there are still plenty of things going on throughout the city and surrounding areas so that you'll still be entertained throughout your stay! Be sure to do some of your holiday shopping in Chicago while you're here, exploring all of the deals that many of the stores have going at the time!

For even more deals, plan your trip with Chicago Traveler to find the best deals on things to do in Chicago and even all the currently Chicago hotel deals that will save you big on your stay! Some of our favorite fall deals in Chicago for hotels are:

  • The Countdown to Winter 2013 at MileNorth which can save you up to 25% on your stay, 
  • The shopping package at Best Western River North where you'll get a $50 shopping gift card to The Shops at North Bridge, plus tons of other great Chicago shopping coupons or 
  • Package deals that get you access to some of the best museums in Chicago for a discounted price, or free admission in some cases! 

Chicago Traveler is here to help you enjoy Chicago this fall for even less so that you have more to spend on all the other great things going on this season!