Date Night: Where To Go & What To Wear

Is it just us, or is Chicago especially romantic in the fall? Sunsets over the river, crunchy leaves on the sidewalks, and a somewhat-brisk breeze are the perfect backdrop for sentimentality. Okay, and maybe it also has something to do with the fact that we're not sweating 24/7 like we do in July, but there is a certain air about a Chi-town October that gets us in the mood for love. So, whether you're planning a group date or an evening out with your S.O., we've got the three best spots for a fall outing — and the no-fuss outfits to match. Here's to a great night!
PumpRoom_Photo: Courtesy of Pump Room. Pump Room
We're all about Jean-Georges Vongerichten's farm-to-table approach to his menu, and the atmosphere of Pump Room has "date night" written all over it. Though the brunch here is ah-mazing, it's the evening transformation that's got us excited. At night, the resto's bar turns into a supper club that captures all the glamour of the '30s and '40s, while offering a modern twist on cuisine. Add in a dreamy cocktail menu, and you've got the perfect excuse to get a little dressed up. Try out this jumpsuit for a classy outfit that isn't too over the top. Romantic, no?

Pump Room, 1301 North State Parkway (at East Goethe Street); 312-787-3700.

Clockwise from top left: Buckle Daytrip Statement Necklace, $12.95, available at Buckle; Zara Jumpsuit With Lace Yoke, $99.90, available at Zara; Dorothy Perkins Metallic Striped Clutch, $29.99, available at Dorothy Perkins; Lipstick Queen Sheer Lipstick in Medieval, $22, available at Bloomingdale's; Dolce Vita Kana D'Orsay Heel, $159, available at Urban Outfitters.

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SecondCity_Photo: Courtesy of Second City. Second City
Home to many a comedy legend — and a seemingly never-ending hiring pool for Saturday Night Live — Second City is a must for date night. It's the perfect opportunity to incorporate entertainment with some light conversation over drinks. We personally recommend A Clown Car Named Desire this month. And, hey, you may even catch a performance by the next up-and-coming comedian. This outfit strikes the perfect happy medium between casual and dressy.

Second City, 1616 North Wells Street (at West North Avenue); 312-337-3992.

Clockwise from top left: Kenzo Casual Trouser, $408, available at The Corner; Honor Heart Jeweled Collar Top, $1,195, available at Matches; Sephora & Pantone Elemental Energy Lacquer in Water, $10, available at Sephora; Aldo Fearghusa Boot, $130, available at Aldo; H&M Bag, $79.95, available at H&M.
DriveIn_Photo: Courtesy of Cascade Drive-In. Cascade Drive-In
The drive-in is a somewhat-aggressive first-date idea, but if you've been out with someone a few times and think you'd like to keep them around, this is a great investment date spot. You see, drive-ins are a dying bit of Americana, and the nostalgia makes the outing all the more romantic. Plus, it's replete with snuggle opportunities, and Cascade is a great Chicago spot for just this activity. With showings on Fridays, Saturdays, and Sundays, you can catch a flick under the stars. Get cozy in a jeans-and-sweater combo, and bring a blanket for added comfort.

Cascade Drive-In, 741 North Avenue (between Prince Crossing and Fair Oaks roads); 630-231-3150.

Clockwise from top left: Dorothy Perkins Ivory Chunky Jumper, $39, available at Dorothy Perkins; Dondup Ripped Skinny Jean, $326.16, available at Farfetch; Vera Meat Bunny Love Ring, $48, available at Vera Meat; Threshold Woven Throw, $19.99, available at Target; Forever 21 All-Day Tote, $29.80, available at Forever 21; Senso Lucky Heeled Ankle Boots, $323.92, available at ASOS.

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