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Top 10 Original, Mostly Free, Date Ideas for Chicago Singles Moving to Chicago

Where do you go on dates in Chicago? If your answer includes the words “dinner” or “movie”, you need help. People living in Chicago have so many choices that sticking to buzz 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. Dates are a reflection of who you are, so show him (or her) how creative you can be by trying one of these creative but simple dates.

The best part – these suggestions are more or less free. This way, you can impress your date while keeping your wallet safe.

10. Butterfly room at the Peggy Notebaert Natural History Museum – Having hundreds of insects flying and landing on you doesn’t sound very romantic, but it’s a completely different story when it comes to butterflies. Get there at mealtime, when you can see the most colorful butterfly species at once. 2430 N. Cannon Drive

Cost: Free

9. Green mill – I wanted to limit this list to just one bar, music and dance venue, so the famous Green Mill was the natural choice. Chicagoans know that the Green Mill was Al Capone’s old hangout and still has that Roaring 20’s vibe. You can dance every night to jazz or swing music with your date. 4802 N. Broadway

Cost: $5-$10 Cover

8. Myopic bookstore – Bookstores are great date places because thousands of books can stimulate a thousand topics of conversation. But Myopic in Wicker Park is more than a used bookstore; this is a fun maze of books. So many winding passages of old books, one feels like Indiana Jones exploring secret ruins. 1564 North Milwaukee Avenue

Cost: $0. Unless you buy a book. The people at Myopic probably wouldn’t like it if I didn’t mention this.

7. Duck feeding – Try this. Take your date to Walgreens and buy a loaf of bread. Then head to the nearest duck pond, sit on the water’s edge and laugh with your date as you watch your feathered friends scramble for morsels. Many Chicago parks have duck ponds, but there’s a good one near the Peggy Notebaert Museum of Natural History. Maybe a little butterfly duck sale? 2430 N. Cannon Drive

Cost: $1.50 for bread

6. Too much light makes the baby blind Chicago is known for its comedy, and there are many different comedy venues for dates like Second City or iO. But I recommend “Too much light blinds the baby” by the neo-futurists. Short, sweet and diverse, you can see 30 plays in 60 minutes. These pieces are constantly changing, you can come back here a few months later. 5153 N. Ashland

Cost: Tickets are $9 + roll of a single six-sided die ($10-$15 depending on your luck)

5. Dave & Busters Listen, Dave & Busters can be a great date if you plan it right. Have your date pick a prize from the ticket booth, then spend the evening playing games together and trying to get enough tickets for the prize. Suddenly, your date has a goal you can work towards together. Yes, the awards suck, but it will be a symbolic reminder of the winning teamwork that won it. 1030 N. Clark

Cost: About $20. Go half price on Wednesday.

4. Picnic in the nearby park Simple? Naturally. Effective? Totally. There is no overpriced restaurant on Earth more romantic than a picnic outdoors in a secluded spot. Keep it simple, don’t forget to bring napkins, cutlery and napkins, and drink some wine while you’re at it. You can do this at any park in Chicago, so for convenience, pick one that’s close to you or your date.

Price: $10-$20 for food

3. Piano bars Why sit in a bar drinking when you can sing and tune in to a live show? Piano bars like “Howl at the Moon” or “Davenports” are a fun and exciting way to spend an evening with someone you want to get to know better. Listen to the tracks or request them – the shows are quite interactive. Howling at the Moon – 30 w. Hubbard St, Suite 200. Davenports – 1383 N. Milwaukee.

Cost: possible cover charge + tips for the pianist

2. SummerDance or Ice Skating in Grant Park This is a double whammy as I don’t want to offer dating ideas that are seasonal. In the summer months, you can take your date to a free dance class at SummerDance, and in the winter, you can go ice skating for free at Millennium Park.

Cost: Free SummerDance. Skating is free, although if you don’t have your own skates, you have to pay for a skate pass.

1. Osaka Japanese Garden – You can find this hidden gem behind the Museum of Science and Industry. This beautiful garden has many unique flowers and plants that mostly grow in Japan. This often secluded spot, carefully maintained by the Chicago Park District, 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.

Cost: Free

Do you have any other great ideas for moving to Chicago? Check out our moving to Chicago blog at New In Town Chicago for fun and helpful tips and tricks for those moving to Chicago or already living in Chicago.

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