Chicago Romance in the Fall: Recommends These Romantic Fall Chicago Acitivies

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Fall brings with it a feeling of romance in Chicago. With the wonderful change in colors, fresh feeling air, and incredible possibilities for Chicago exploration, travelers and locals should be cuddling up and enjoying Chicago in the fall.

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Fall brings incredible opportunities for sweethearts to snuggle up and enjoy the changing seasons together.

Couples should be eating spaghetti and smooching, like in Lady and the Tramp. Fall brings incredible opportunities for sweethearts to snuggle up and enjoy the changing seasons together. has put together these ideas for couples to take advantage of in the coming colorful months.

1.) Chicago Lakefront Trail
A walk along the Chicago Lakefront Trail never gets old, and during the fall months the trail is less congested and love birds can leisurely stroll without worrying about being mowed down by a crazy rollerblader wearing dolphin shorts (making a come back from the 80s).

Rent a bike, take a walk, or sit on the side and people watch for hours. This Chicago Lakefront Trail gives love birds the perfect opportunity to just enjoy each other’s company.

2.) Cocktails on the Top
With incredible views from any direction, maximizing the romance of Chicago from a rooftop bar is the perfect date night opportunity. With mild weather hopefully sticking around for a while longer, take advantage of the crisp Autumn air from above. The Terrace at Trump is open until weather drives everyone back indoors.

3.) Lincoln Park Lily Pool
Ahhh, amor. A more lush and vibrant place cannot be imagined. With fall bringing in new and wonderful colors, grab a sweetie and spend the day languidly lounging by the Alfred Caldwell Lily Pool in Lincoln Park. Free docent tours are also available until early October, so don’t miss out on the chance to walk hand in hand with your better half while learning about the Lincoln Park Conservatory.

4.) Lakefront Bicycle Tour
Chicago is a beautiful and bikeable city, so why not go off the beaten path with Bobby’s Bike Hike Lakefront Tour. For tourists coming to Chicago, this is a wonderful opportunity to explore the city. This tour features the Playboy Mansion, Oprah’s House, the Lincoln Park Zoo, and the stretching Chicago Lakefront.

5.) Date to Chicago Bears
Set, hike! There is nothing more fun and eventful than a Chicago Bears game. The editors of recommend this for a thrid or fourth date kind of idea (or just grab the gal you’ve been with since the Ice Age). This season looks like it’s going to be a winning one (go Bears!), so take a sweetheart to the game, grab a hotdog and beer, and enjoy a fun-filled day of rooting for the best!


Chicago is one of the top vacation destinations in America famous for its annual events, popular foods, and architecture and top sports teams. guides travelers to all the best things to do, top places to eat and deals on the best places to stay in Chicago.

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Lindsey Skinner
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