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21 Spectacular Date Ideas in Chicago in 2020

With Valentine’s Day fast approaching, it is a great opportunity to recommend some great date ideas here in Chicago. Here are some options that will hopefully make you as happy together as hops and barley. Enjoy!

1. Take a Walk in a Chicago Park

a man walking down a dirt road

Chicago’s motto is urbs in horto and it means “city in a garden.” It should be no surprise that we have wonderful parks that you can visit for free. Take a stroll with your date in Millennium Park where they often have free events like movies and concerts, too. Large parks like Lincoln Park and Jackson Park are great spots. There are lesser known parks like Ping Tom Memorial Park in Chinatown that are wonderful and many neighborhoods have their own parks that you can meander through as well. Here’s the Chicago Park District website: Link.

2. Chicago Beer Experience Beer Tour

a man talking on a cell phone

We’ve had many couples on our beer tours and know first-hand how perfect it can be! On our tours, you and your special friend will be able to learn about Chicago and beer. The best part – tasting beer – will loosen you both up and calm your nerves. The best part is that you’ll have a tour guide to handle some of the talking, so you can enjoy each other’s company in a low-pressure environment while taking in some fun facts about our city’s past. Link.

3. Paint & Sip

a woman holding a wine glass

Photo courtesy of Mcgrailsean

Grab and paint brush and, more importantly, a bottle of wine at a BYO paint class to break the ice. The best part: no one is expecting Monet or Picasso, so just have fun. Here are a few highly-rated options: Pinot’s Palette (Link,) bottle & bottega (Link), Wet Paint (Link), VIP Paints (Link), Sip & Paint (Link), and Museica (Link).

4. Laugh at a Comedy Show

Deon Cole standing on a stage in front of a curtain

Comedian Dione Cole, photo courtesy of LOL Comedy

Laugher is often the best medicine and studies show that is even true for dating. Share a laugh at one of Chicago’s world famous clubs. Most notorious of the bunch is Second City, which has fed many comics to Saturday Night Live and stardom. There are also other clubs, such as iO TheaterZanies, and The Laugh Factory. Local venues and bars often will have nightly events, too.

5. Robot Date Night


a clock on a table

Photo courtesy of Robot City Workshop

One of the most unique ideas: nerd out and build a robot together! The Robot City Workshop hosts a BYO after hours evening event several nights a week. You’ll even get two Metropolitan beers as part of your ticket. (Link).

6. Gaze at Animals at the Lincoln Park Zoo

a polar bear is swimming in the water

Lions, Tigers, and…kisses? Oh my! As one of the only free zoos in the country, the Lincoln Park Zoo offers a great budget option. They also sometimes have paid specialty events, too, such as their Adults Night Out series in the summertime. Link.

7. Come Together at an Escape Room

a man and a woman sitting on a table

Photo courtesy of David Hofmann

Test you and your date’s wit and intelligence with an escape room! If you aren’t familiar with these events, they give you a list of clues and time limit to escape. And if you fight or argue a lot during this time? Easy red flag to break up. Some popular options include The Escape Game (Link), Escape Artistry (Link), Room Escape Adventures (Link), Fox in a Box (Link), and Escape House (Link).

8. Cooking Class

a man and a woman standing in front of a table

Show off your culinary talents…or at least your desire to whip up something tasty…by taking a cooking class! Many of these are also BYO, which is even better. Here are some of the best:

Chopping Block (River North & Lincoln Square)

Cook Au Vin (Bucktown)

Cooking Fools (Wicker Park)

Get in the Kitchen (Lakeview)

Give Me Some Sugar (Roscoe Village)

Naveen’s Cuisine (Wicker Park)

Read It & Eat It (Lincoln Park)

The Wooden Spoon (Andersonville)

Social Table (Lincoln Park)

9. Culture at World Class Museums

a group of people standing in front of a mirror posing for the camera

Photo courtesy of Phil Roeder

Show your date how cultured you are by visiting one of Chicago’s incredible museums. Favorites include the Art Institute, the Field Museum, the Museum of Science and Industry, Adler Planetarium, the Chicago History Museum, and the National Museum of Mexican Art. There are plenty of lesser known, often specialty museums as well, such as The International Museum of Surgical Science.

10. Board Games & Brews

a cake sitting on top of a wooden table

From Chutes and Ladders to Settlers of Catan to Scrabble, enjoy a game night with your bae. While many bars and taprooms are game friendly, here are some with board games available on-site:

Kibbitznest Books, Brews & Blarney (Link)

Relo’s Board Game And Dessert Café (Link)

Guthries Tavern (Link)

11. Cast a Spell at a Magic Show

a person wearing a suit and tie

Photo courtesy of nosha

Put some magic in your relationship…by heading to a magic show! There has been a recent revival of this type of entertainment. Here are some current places to enjoy: The Magic Parlour (Link), the Chicago Magic Show (Link), and Trickery (Link).

12. Lovers at the Lakefront

a person riding a motorcycle on a city street

Leisurely saunter hand-in-hand or bike ride on Chicago’s glorious lakefront! There are even beach bars you can stop at along the way to order up a cocktail.

13. Sculpt Together at an Art Class

a man sitting on a table

We put paint and wine as its own category, but there are other art classes you can enjoy as well. For example, there are pottery glasses (Check out Penguin Foot [Link], Creative Claythings [Link], Park West Ceramics [Link], Lincoln Square Pottery Studio [Link]) and even glass blowing studios (Ignite [Link], Chicago Glass Collective [Link], Talisman Glass [Link]). Certainly, a more unique option that should make things interesting!

14. Darts & Ping Pong & Other Bar Games

There has been a recent proliferation bars that feature particular games, such as ping pong (Spin [Link], Acebounce [Link]), darts (Flight Club [Link]), and even shuffleboard (Royal Palms [Link]). There are also numerous arcade bars and, of course, don’t forget bowling. Another change to test your skills and witty banter with a potential mate.

15. Fireworks @ Navy Pier

fireworks in the sky

Navy Pier’s reputation as a tourist trap is often well-deserved, but Chicago is sinking a lot of money into this institution and breathing some more life into it, including bars that are more fun. Additionally, from Memorial Day through Labor Day, they feature free fireworks shows on Wednesday and Saturday nights. A stroll down the pier and a show will hopefully lead to some fireworks in your love life.

16. Spa & Sauna @ Aire Ancient Baths

a tall glass building

Photo courtesy of Aire Ancient Baths

Chicago has plenty of spas and some old-school bathhouses, but for a fancier time that is more friendly for couples, check out the Aire Ancient Baths (Link). They have baths and steam rooms of various temperatures and designs that you can explore together. You can even add on a massage or other treatments.

17. Take a Date to New Heights on a Helicopter Tour

a river running through a city

Photo courtesy of Chicago Helicopter Experience

See the city in an exhilarating way! Whether during the day or at night, the impressive skyline will take your date to new heights. Check out Chicago Helicopter Experience. Link.

18. Take in a Theater Show

a traffic light on Chicago Theatre street

Another chance to show culture by heading to one of the city’s many theatre shows. Broadway in Chicago (Link) regularly shows better-known acts right downtown along with other downtown venues. The neighborhoods also have wonderful theatre, such as the Steppenwolf Theater (Link) the Greenhouse Theater (Link), and Victory Gardens Theater (Link) in Chicago’s Lincoln Park neighborhood.

19. Mix up Passion with Fancy Cocktails

a woman holding a bottle of wine

Head to the city’s many cocktail bars for a fancy mixed drink. Ambiance + booze = perfect environment for a great date. Too numerous to list here, but a simple Google or Yelp search will turn up plenty of options.

20. Stroll along the Chicago Riverwalk

a bridge over water with a city in the background

Photo courtesy of Ecoscapes

Chicago has heavily invested, transformed, and created a 1.25-mile path along the Chicago River right along the north side of the Chicago Loop. It can get packed in the summer as more and more restaurants and other vendors open their doors to tourists, but it can be quite a romantic refuge in the winter as well. Link.

21. Tango Together when Dancing

a man and woman holding hands

Dancing can be sensual and romantic. You and your date can hold each other at a studio and many bars and restaurants feature particular nights of different styles of dancing. From salsa to ballroom, there is something for everyone. Plus, you’ll have to put your hands on each other.

Whatever you choose, best of luck in life and love!

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