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Top 10 Original, Mostly Free, Date Ideas for Chicago Singles Moving to Chicago
Where do you go on a date in Chicago? If your answer contains the words “dinner” or “movie,” you need some help. People who live in Chicago have so many options that going with the hum-drum traditions automatically puts you in the “friend zone.”
Singles moving to Chicago should be prepared. Dates don’t have to be expensive, but a successful date should be fun, exciting and original. Your dates are a reflection of who you are as a person, so show her (or him) how creative you can be with one of these imaginative, yet simple, date ideas.
The best part – these instructions are more or less free. So you can impress your date while being kind to your wallet.
10. The Butterfly Room at the Peggy Notebert Nature Museum – Hundreds of insects flying around and landing on you may not sound very romantic, but when they are butterflies, it’s a whole different story. Arrive around feeding time when you can see the most species of colorful butterflies at once. 2430 N. Cannon Drive
9. Green Mill – I wanted to limit this list to just one bar, music and dance venue so the famous Green Mill was a natural choice. As those who live in Chicago know, the Green Mill was an old hangout of Al Capone and still has that 20s vibe. Every night you can dance to jazz or swing music with your date. 4802 N. Broadway
Cost: $5-$10 cover
8. The Myopic Book Store – Bookstores are great date places because thousands of books can spark a thousand conversation topics. But Myopic in Wicker Park is more than just a used bookstore; It’s a funhouse maze of books. There are so many old passages from the books, you feel like Indiana Jones is looking for some secret ruins. 1564 North Milwaukee Avenue
Price: $0. Without buying the book. Myopic people might not like it if I don’t mention it.
7. Duck feed – Try this. Take your date to Walgreens and get bread. Then head to a nearby duck pond and sit on the water’s edge and laugh with your date as you watch your feathered friends frolic. Many Chicago parks have ponds with ducks, but a good one is near the Peggy Notebert Nature Museum. Maybe go for some butterfly on duck action? 2430 N. Cannon Drive
Cost: $1.50 for bread
6. Too much light makes the baby blind Chicago is known for comedy and places like Second City or IO have many different comedy shows to take a date to. But I have to recommend “Too Much Light Makes the Baby Go Blind” by Neo-Futurists. Short, sweet and full of variety, you get to see 30 plays performed in 60 minutes. These plays are constantly changing so you can swing back here after a few months. 5153 N. Ashland
Price: Ticket $9 + roll of single six-sided die ($10-$15 depending on your luck)
5. Dave and Busters Hear me out, Dave & Busters can be a great date if you plan it right. Ask your date to pick up a prize from the ticket prize booth, then spend the evening playing games together, trying to get enough tickets to win it. Suddenly, your date has a goal you can work towards together. Yes, the prizes are absorbing, but winning them will be a symbolic reminder of your winning teamwork. 1030 n. Clark
Cost: About $20. Go half price on Wednesdays.
4. Picnic in a nearby park Easy? Of course. Effective? Absolutely. There is no overpriced restaurant on earth more romantic than a picnic in a secluded spot. Keep it simple, remember to bring napkins, cutlery and napkins, and grab some wine while you’re at it. You can do this at any Chicago park, so pick a date near you or one that’s convenient for you.
Cost: $10-$20 for food
3. Piano Bar Why sit and drink at a bar when you can sing and interact while at a live show? Piano bars like “Howl at the Moon” or “Davenport’s” are a fun and exciting way to spend an evening with someone you want to get to know better. Listen to tune shows or make requests – the shows are very interactive. Howling at the Moon – 30th. Hubbard St, Suite 200. Davenports – 1383 N. Milwaukee.
Cost: Possible cover charge + tips for pianist
2. Summerdance or ice skating at Grant Park This is a double whammy because I don’t want to recommend any date ideas that are seasonal. During the summer months, you can take your date to a free dance lesson at Summerdance, and in the winter go ice skating for free at Millennium Park.
Cost: Free for Summerdance. Ice skating is free although you have to pay to rent skates if you don’t have your own.
1. Osaka Japanese Garden – You’ll find this hidden gem behind the Museum of Science and Industry. This beautiful garden has a variety of unique flowers and plants that grow mainly in Japan. Maintained by the Chicago Park District, this secluded location features the Moon Bridge and East Lagoon Falls. Grab a camera and compete with your date for the best photo. 5800 S Lake Shore Drive.
Got more great ideas for singles going to Chicago? Check out our Going to Chicago blog at New in Town Chicago for more fun and helpful tips and secrets for people visiting Chicago or Chicago residents.
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