10 Perfect Fall Dates in Chicago
Thanks summer! It’s been real, but everyone knows that fall in Chicago is the best time of year. This is true not only because of the renewed cultural celebrations, festivals or even the weather, but because everyone is itching to enjoy the last few months before the cold of winter sets in. In this beautiful season, there are plenty of activities and dates for couples to do both indoors and out. From food and pub crawls to night hikes and paintball, here are some ideas for pitch-perfect dates this fall.

Tour Chicago’s best food.


Deep dish pizza, Chicago hot dogs and Italian beef. These are only a few of the delicious dishes Chicago has to offer. If you and your date can’t decide on what to eat on your next night out, why not sample them all? This Chicago food crawl tour caters to anyone’s tastes (even vegetarians) as it takes you through the city’s most famous and frequented foodie spots.

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Cycle your way through Second City.


Chicago is a city of neighborhoods; North Side, South Side, Old Town, Lakefront, Gold Coast—the list goes on! It’s hard to venture out to other neighborhoods when your friends, family and favorite restaurants all live in the same one. That’s why this bicycling tour of Chicago (which includes a bike rental and helmet) is so popular. In one day, you can explore a number of neighborhoods without stretching your budget—just maybe your legs, if you know what’s good for you.

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Scare yourself silly touring Chicago’s ghost town.

walking tour
culture tour
historic tour

Happy Halloween! If you’re looking for a date idea that will celebrate this spooky holiday, then take a tour of the creepiest crawls in Chicago. Hosted by a local legend expert, this tour will take you on a journey through Chicago’s dark history. The Congress Hotel, the sites of H.H. Holmes and the site of the Eastland Disaster are just some of the colorful haunts that will leave you pale. Put on your walking shoes, grab a flashlight and shoulder your ghost-hunting gear, but remember: this tour is not meant for the faint of heart.

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Pick a pumpkin in DeKalb County.

Parades, pie eating contests, carnival rides and 1,000 decorated pumpkins—what more could you ask for? To celebrate autumn in style, you and your partner should head over to the Pumpkin Festival in nearby Dekalb County for a day away from the city to take in the new season. Visit the local vendors for some delicious treats and pick up some festive decorations to bring home so that you can ring in the holiday in style.

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Fly like an eagle—or a small passenger plane.

learn to fly
pilot lessons
flight school
Lake Michigan

Autumn—the time of year when the leaves change color and the air turns crisp. As beautiful and scenic as the view is from the ground, it’s even better miles above in the air! On this Lake Front Flight, you’ll be up, up and away in a small aircraft that will have you soaring over the Windy City. Take in the beautiful sights with your partner and learn the basics of flight training. While you and your date won’t be able to join the mile-high club (it’s a pretty small plane and the instructor is third-wheelin’), you’ll cruising the skies in no time.

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Relieve some tension—shoot your partner with paintballs!


Winter is coming, but for now, make sure you enjoy the colorful fall season by adding some color of your own during a morning paintball match.This high-intensity activity may get your and your date’s hearts racing in just the right way. With games divided between advanced players and beginners, grab your date and your friends of all skill levels to battle it out before the weather gets too cold.

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Hike-and-seek in the dark.


Is there such a thing as a romantic hike? We believe so, especially if it’s at night. No matter how many times you’ve hiked to your favorite spot during the day, it’s a whole new world at night. Come see the other side of Taltree Arboretum & Gardens on this majestic Night Hike. Get away from the city for a romantic evening under the stars, and if it gets chilly, you may just have to cuddle up for some late-night warmth.

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Visit Second City’s best film spots.

movie tours
chi town
windy city movies

It may be hard to believe, but 75 films have been made in Chicago over the last 100 years. From blockbusters to indies, these Chicago-filmed stories truly capture the city’s vibe, giving audiences the feeling of actually being there. Since you live in Chicago, it’s not hard for you to transport yourself to those spots in reality. In this film locations tour of Chicago, you and your partner will discover iconic film locations in neighborhoods like Gold Coast, Wrigleyville, Old Town and Lincoln Park. What better way to enjoy a fall day than by skipping your regular movie viewing and seeing dozens of films out in the world instead.

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Sample seasonal beer at the Chicago Botanic Garden.

Spend an evening at the Chicago Botanic Garden with your date to enjoy seasonal beer samplings from local breweries. A great way to get a little boozy as you take in the sights of Chicago’s beautiful exhibits and greenery scenery, this is a perfect relaxing fall date. Make sure to get your tickets in advance, as this popular event sells out quickly!

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Experience your own “Drunk History” night.

pub crawl

History doesn’t have to be about ancient artifacts, far-away battles or great heroes. In fact, a lot of the most interesting history is right under your nose, waiting to be discovered. This historic bar tour combines drinking with history, exploring Chicago’s early days of prohibition, jazz and speakeasies. It’s the perfect pub crawl for history nerds with a penchant for getting their drink on or anyone looking to delve deeper into the mysteries of Chicago’s late-night scene.

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