32 Secret Places In Chicago To Bring Your Girlfriend This Fall

There's so much to see in this city!
32 Secret Places In Chicago To Bring Your Girlfriend This Fall

Now that fall is around the corner in Chicago and the too hot, too humid days are (hopefully) behind us, there is no time like the present to get out and explore all the beautiful spots the city has to offer!

Whether you are after secret gardens, bars, eateries, or just unique date spots - we've got you covered. Chicago locals are so lucky to be in a city where there is an abundance of activities and places to head out and explore, so add all of these spots to your fall bucket list with your significant other!

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Hoosier Mama Pie Company

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Hoosier Mama Pie Company is an artisanal bakery that specializes in sweet and savory pies made by hand with the best ingredients! Nothing beats sharing a huge piece of apple pie and a cup of bottomless coffee.

Milton Lee Olive Park

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This park memorializes Milton Lee Olive III, who was the first African American awarded the Medal of Honor for his service during the Vietnam War. If you're lucky, you might witness a marriage proposal or two as it's a very popular spot to pop the question!

Elks National Memorial

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If you are a fan of beautiful architecture, this is one spot in Chicago you cannot miss. The memorial was built in 1926 to honor Americans who sacrificed their lives for their nation. With its massive dome, it's an iconic structure to this day.

Lurie Garden

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Yet another popular romantic spot for marriage proposals, the Lurie Garden is a great spot for a walk during the warmer months. Located in Millenium Park, this spot is a true urban oasis—an escape from the city right in the heart of downtown!

 Miko's Italian Ice

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Italian ice is truly the perfect treat. Similar to sorbet, it is made with fruit or other flavorings and is one of the most refreshing things you can have on a hot day. Head to Miko's for some interesting dairy-free flavors including banana chip, sour cherry, rhubarb, pumpkin spice, or maybe just grab one of the classics!

Room 13

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This spot is truly a hidden gem. It's one of Chicago's fine speakeasy bars serving up classic cocktails and recipes that hail from the Prohibition era. The spot is accessible to guests of the Old Chicago Inn, as well as Room 13 members, and follows a strict dress code!

Pequod's Pizzeria

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You can't be in Chicago and not have an opinion on who makes the best deep-dish pizza. Check out Pequod's Pizzeria for some seriously cheesy and delicious pizza pies!

The Wormhole

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One of Chicago's fine coffee roasters, this spot is dedicated to the 80s—complete with a DeLorean! Head here for a chill date and drink iced coffee from locally roasted coffee roasters.


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Get in touch with your competitive nature and head to SPiN, a great spot to hangout featuring loads of ping pong tables, as well as food, drinks, and DJs! If you're looking for something different than the usual bars on the weekend this is your go-to spot.

Saint Lou's Assembly

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You know what fall means — the last few days of patio season! Saint Lou's Assembly is one of the hot spots, with a huge outdoor seated area that is perfect for dates or with a group of friends!

Garfield Park Conservatory

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Whether it's raining or shining, the Garfield Park Conservatory is a great place to visit with your significant other. Not only is it a peaceful spot away from the noise of the city, but the entire conservatory is adorned with plants, flowers, and trees of all kinds!

Randolph Street Market

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The Randolph Street Market is held monthly and offers upscale wares such as antiques, jewelry, and art—during the warm sunny days, it can be a great spot to have a walk outside and hunt for treasures! Although not technically a secret spot, you can truly find some hidden gems if you look hard enough.

12th Street Beach

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This spot is one of Chicago's smaller beaches, however, it is right in the heart of the city—an unlikely place for a beach! It makes up for its small size by its lack of crowds, so if you're looking for a remote spot to relax on a hot day, this is your place!

Del Campo Tacos

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Located right near 12th Street Beach, if you're looking for a lakefront vendor that serves something you can snack on the beachDel Campo Tacos is where to go. What could be a better combination than tacos on the beach before it gets too cold?

Hala Kahiki Tiki Bar & Lounge

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Why not head out to a tiki-themed bar and have a night of testing out the long list of festive drinks? With a patio area for the warmer days, this is the perfect date spot.


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This spot will most definitely entice couples who are book-lovers. An offbeat hangout spot featuring books and games paired with food, coffee, and drinks—all in a wifi and laptop-free zone to encourage face to face communication!

The Catcade

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This non-profit rescue shelter cum cat cafe is a great secret date spot featuring arcade games and adorable cats! This spot is perfect for any cat lover. Who doesn't love bonding over a love for cute animals?

Bottle & Bottega

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Not an art class, but an art party! This fun activity is not extremely well-known yet, but it should be—painting and wine sounds like the greatest combination ever. If you're after a new date idea, here's where you should go!

Promontory Point

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A man-made peninsula on the shore of Lake Michigan, this spot boasts one of the best spots to view the sunset in Chicago—and it can be super romantic to sit and watch it together!

Alfred Caldwell Lily Pool

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This hidden oasis inside Lincoln Park is accessible between April and November and is the perfect spot to explore during these months. The only sounds you will hear in this secret oasis are bird songs and the sound of a gentle waterfall, so come here for some peaceful downtime!

The Garden of the Phoenix

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Perhaps the most enchanting section of Jackson Park, the Garden of the Phoenix is a Japanese strolling garden that is reminiscent of the traditional gardens in Osaka, Japan. Featuring a permanent art installation by Yoko Ono, this is a perfect serene spot for a fall's day walk with a significant other.

Mott St

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Brunch is the best meal of the day—we can all agree on that. And when you're tired of the same old eggs benedict, pancakes, and traditional brunch menu items, you can head to Mott St—an Asian spin on all the classic items. Try the pork jowl skillet, coconut pancakes, or kimchi fried rice!

Ping Tom Memorial Park

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For a unique spot to snap some great pictures of architecture or have an explore, Ping Tom Memorial Park is your go-to. Board the Chicago Water Taxi, get out in Chinatown, and then head over and explore the park's riverfront pagoda. The spot is not widely known to visitors—so if you want a secret spot to go on a leisurely walk, here it is!

Adler After Dark

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Head to the Adler Planetarium's after-hours nights which are open to those over the age of 21, offering open access, unlimited shows, and unique entertainment every third Thursday of the month! With themes that change every month, no After Dark is ever the same, and it is one of the most fun and not-so well-known date ideas during the fall!

Original Rainbow Cone

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One of the true hidden gems of Chicago, this is a long-standing seasonal ice-cream spot that serves cones, shakes, sundaes, and banana splits. Come here for an old-school date, and of course, you have to try their iconic rainbow cone!

Game Room

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This spot is so hidden that it doesn't even have a sign with the name on it—inside you will find games, food, and drinks! Game Room is a fun spot for a lowkey hangout, with a great space!

Scooter's Frozen Custard

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Yet another frozen dessert on the list—frozen custard is smooth, creamy, and rich. Made fresh daily using local ingredients, this is one spot you absolutely cannot miss! Honestly, is there anything greater than sharing amazing food experiences with your significant other?

The J. Parker

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Enjoy the sunshine at one of Chicago's rooftop bars and restaurants with some amazing views of the city and Lake Michigan. Located atop the Hotel Lincoln, come here for a great night out with a wide variety of cocktails!

Kingston Mines

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Open until 4am most nights (until 5am on Saturday nights), Kingston Mines is one of the city's best blues clubs serving cocktails as well as a full menu of BBQ options. This is a great secret spot for music aficionados!

Riverbank Neighbors Trail

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This serene and hidden riverbank is the perfect spot for a leisurely stroll or even just to sit on the riverbank and appreciate the peacefulness of the river. Just across from the popular Horner Park, you'll be charmed by the quiet and privacy of this particular spot!

Big Monster Toys

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Take the coolest photo op this side of the door in Monsters, Inc. outside of this toy and game company. Yup, this is basically the coolest door in the world.

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