Date Night in Chicago: Three Approaches to The Great First Date

Bruce Sturgell

By Bruce Sturgell

There’s no real secret code to the great first date. It’s equal parts chemistry, interest, and sheer luck. Since you can’t control chemistry or luck, you can focus on making the date fun and memorable. If you’re in the Chicago area and you’re looking for something to do, consider these three ideas for a date your partner won’t soon forget.

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Cheap Date: Want to make an impression, but can’t exactly pony up the cash for Charlie Trotter’s? Consider taking your date to The Art Institute of Chicago (111 S Michigan Ave) to view some of the over 300,000 works of art in its permanent collection. From Byzantine sculptures to Picasso’s Old Guitarist, you’ll find amazing creations that’ll give you a lot to discuss over dinner. Best of all, The Art Institute offers free admission every Thursday from 5 to 8pm to Illinois residents.

All that perusing of some of the world’s best art can make a guy hungry – continue the evening with dinner at Longman & Eagle (2657 N Kedzie Ave) for creative, yet relatively inexpensive fare such as wild boar sloppy joes for $14, or Ricotta Gnuddi, Chanterelle Mushrooms, Tot Soi, Black Garlic Tuille, and Saffron Corn Puree for $12.

Romantic: There are lots of things you can do on a romantic first date in Chicago. From carriage rides around the city’s various neighborhoods, to a trip to the Lincoln Park Conservatory (541 N. Fairbanks) to see the exotic plants, or even enjoying a bottle of wine while you paint a masterpiece at Bottle & Bottega (2900 N. Lincoln Ave), finding something fun and romantic to do in the city is pretty easy.

If money is no object, cap off your evening with an intimate dinner for two at Les Nomades (222 E. Ontario St) for some of the finest French cuisine the city has to offer. Be sure to try the roasted duck breast and confit duck leg.

Looking for a romantic dinner without breaking the bank? Head to Tango Sur (3763 North Southport Ave) for authentic Argentinean cuisine and an intimate candlelit atmosphere. If you’re a meat lover, this is the place for you. Get there early to avoid the lines, and, as this place is BYO, you’re welcome to bring your favorite libation.

Fun and Offbeat: So candles and fine dining don’t fit your idea of a great first date? You won’t be disappointed if you’re looking for fun, offbeat, or even adventurous things to do on a first date in Chicago. Catch some comedy at Second City (1616 N Wells St), or take a boat tour to get the Chicago river experience, or see some of the city’s best architecture with Wendella Sightseeing Co. (Wendella Dock, 400 North Michigan Ave).

If live music is your thing, take in a concert at the Old Town School of Folk Music (4544 N. Lincoln Ave) for some of the best roots and world music the city has to offer. Lastly, you can take in all the ghosts, gangsters and ghouls that the Windy City has to offer on a Weird Chicago bus tour (600 N Clark St). Take your pick of the ghost tour or the gangster tour and learn more about the city’s secret history.

With these suggestions, you’ll be able to put together a first date that’s sure to make an impression. Do you have more suggestions for great places to visit on date night in Chicago? Tell us in the comments below.  To find your great first date outfit check out or visit the new flagship store on the corner of Michigan Avenue and East Chicago Avenue.

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