Best Date Night Spots In Chicago

November 16, 2015 7:00 AM

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When going out, it helps to know whether your date loves or hates watching hockey or basketball and listening to classical music or hard rock. Tuning in on personal likes and dislikes makes planning easier. But what if you don’t know yet? Fortunately, Chicago has so much going on that there are several options, enough to suit any taste, including these five top suggestions.

Second City Mainstage
1616 N. Wells St.
Chicago, IL 60614
(312) 337-3992

It doesn’t matter if going on a first date or not when taking in a Second City show on its Mainstage. The acts are conversation starters, so you’ll both enjoy the date with little effort. Indeed, the theater’s cabaret-style seating encourages conversation. And you never know if you will be seeing the next Ed Asner, Alan Arkin, Barbara Harris or Elaine May, who were all early Second City alums. Shows sell out, so try to plan ahead. Tickets are typically $23-29. The shows are scripted but also include some wonderful improve moments.

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Adler After Dark
Adler Planetarium
1300 S. Lake Shore Drive
Chicago, IL 60605
(312) 922-7827

You won’t have to hope the sky is clear to romantically gaze at the stars if you go on a date to the Adler Planetarium. Anchoring the far eastern end of Chicago’s Museum Campus, the planetarium is the perfect place to see the city’s magnificent skyline outside on its terrace or inside from its cafe. This is also the place to take a date the third Thursday of the month, when the museum hosts adults 21 and older at its Adler After Dark music and entertainment themed events. Nov. 19 will be Back to the Future, Dec. 17 is Adler After Dark Side (think the Force and Star Wars) and Jan. 21 is First Contact (aliens?). The event runs from 6 to 9 p.m. and costs $20 for general admission ($15 Adler members). Admission means access to all exhibits, galleries and sky shows in three theaters and the Doane Observatory. An additional $5 ticket gets upi a tour of the Observatory, but tickets sell out quickly. After Dark also features special guests and lectures. Alcoholic beverages are available at bars set up for the event. Food and other drinks can be bought in the Adler’s Cafe Galileo.

McCormick Tribune Ice Rink
Millennium Park
201 E. Randolph St.
Chicago, IL 60601
(312) 742-1168 (Ice conditions 312-742-5224)

Ice skate to music with Chicago’s skyline as the background in Millennium Park. No skates? No problem. Ice skating is free and skate rental is just $12. The ice rink is open each year  from the second weekend of November through the first weekend in March. Take a hot chocolate break at the adjacent Park Grill Cafe. The address is Randolph Street but the rink is street side along Michigan Avenue between Washington and Madison Streets.

Related:  Best Places To See Stand Up Comedy In Chicago

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Zoo Lights
Lincoln Park Zoo
Lake Shore Drive at the Fullerton Parkway
Chicago, IL 60614
(312) 742-2000

A zoo visit brings on monkey faces, laughter, maybe selfies and a good time no matter what the age or time of year. For a date at night see Lincoln Park Zoo during Zoo Lights Nov. 27, 2015 through Jan. 3, 2016, when it glows with two million lights. The lights trim trees, illuminate water features and take on animal forms. Of course the real animals are there to visit. The event is free and fun. Food is available at several stands. Zoo lights goes from 4:30 to 9 p.m. on specific dates: Nov. 27-29, Dec. 4-6, 11-23, 26-31 and Jan. 1-3.

Weird Chicago Tour
Bus pick up outside Rock ‘n ‘Roll McDonald
600 N. Clark St. (between Ontario and Ohio Streets)
Chicago, IL 60610
(888) 446-7859

It doesn’t have to be October to visit Chicago’s haunted places or February to see the St. Valentine’s Day Massacre site and other Chicago gangster locals. A Weird Chicago Tour might be perfect if looking for something out of the ordinary. See the schedule by going to “book now” on the website. Tours are typically three hours. Passengers can get off and back on at the various stops. Tours must be booked in advance, and tickets are $35. This is a chance for you and your date to see Chicago from a different perspective.

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Jodie Jacobs is a veteran journalist who loves writing about Chicago, art, theater, museums and travel. Her work can be found on