10 Dates You Should Go On In Chicago This Summer

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Summer is here and love is in the air again. Whether you’re interested in a summer fling or that special someone, Chicago has a plethora of fun places to bring your date. From the touristy spots bound to impress, to the secret hideaways locals like to frequent, here are ten top-notch places to bring your special friend.

1. Signature Lounge at the 96th

With an amazing view of the city, good drinks, and pleasant atmosphere with people from all walks of life, the Signature Lounge at the 96th, in downtown Chicago, is definitely a must for dates with both Chicagoans and visitors to the city alike. The drinks, although pricey (average $14-16 per “specialty” cocktail), allow you to really show your date how dazzling Chicago is. If you time it right and go on a Wednesday or Saturday night, you even can manage to get a glimpse of the Navy Pier fireworks off in the distance.

2. The Violet Hour

Hidden in the vibrant Wicker Park neighborhood is an absolute gem of a bar: The Violet Hour. Although the line to get in can be long, the wait is definitely worth it. Upon entering you are greeted with a dim, intimate, atmosphere with the faint murmur of conversations carrying around the bar. The volume in the bar is just enough to provide comfortable background noise but not enough to drown out conversation with your partner. For a first date the drinks may be a little expensive ($13) but the drinks are well worth it. They are strong, creative, and made by some of the incredibly knowledgeable bartenders who really show off the art of mixology.

3. Intelligentsia Coffee on Broadway

For a casual first “get to know you” coffee date to meeting up in the afternoon for deep conversations before dinner at one of the plentiful restaurants in the area, Intelligentsia Coffee on Broadway is a particularly delightful coffee shop. The coffee is among the best you will find in Chicago, the staff is friendly, and the presentation is incredible. The crowd is often mixed from business professionals to artists working on projects; you can do no wrong bringing a date here.

4. The Armadillo’s Pillow

Honestly, there are so many incredible used bookstores tucked away in the neighborhoods of Chicago that going on a date to any of them would be an excellent idea; however, with the Armadillo’s Pillow you have a fun, charming, shop full of bright colors, crowded bookshelves, and ridiculously comfortable seating. Explore the books and learn about each other’s tastes in literature. And, after you discover some lost gems, it is a hop skip and a jump away from the beach where you can spend the rest of the day reading snippets of poetry to each other as the sun sets.

5. Waterfront Café and Hollywood Beach

Another summertime favorite is the hidden gem Waterfront Café with its delicious selection of foods for a light lunch next to the Kathy Osterman (aka Hollywood) beach. Here you will find a scenic view of the lake, a simple but refreshing menu, and an incredibly friendly staff. On the weekends Waterfront Café also brings in live entertainment for a relaxing and calm afternoon. Go to the Waterfront Café before lounging out on the beach, if you feel peckish while tanning, or after a fun day in the sun.

6. Yoga at the Zoo

It’s probably not the typical date, and in fairness, the Lincoln Park Zoo is a great place for a date on its own. It is free, well cared for, and a nice way to spend an afternoon on a warm summer day; however, sometimes getting a little active with your date and putting yourself into fun positions can create lasting memories. While taking some time to touch your inner self against the backdrop of the Chicago skyline seen through lush trees and bushes this is a fun way to spend some time with a date in a quiet, intimate, yet group, setting.

7. Movie Trivia Night at Logan Theater

Every Tuesday at 8 P.M. Logan Theater hosts Movie Trivia Night. This is a great opportunity to grab some drinks and learn about your date’s movie tastes and knowledge and see if you can work together. This is also a fun opportunity to have a double date or the perfect chance to introduce your date to your movie buff friends.

8. Chicago Shakespeare in the Parks

For a more cultural date make sure to catch the Chicago Shakespeare in the Parks performances this summer. Although Chicago Shakespeare in the Parks is only entering its second year, the reception last year was amazing. Spread a blanket out, watch, and laugh as Shakespeare’s The Comedy of Errors comes alive.

9. Museum Campus in Grant Park

Chicago has an incredible array of museums to delight everyone. Why not spend a day on the Museum Campus in Grant Park? With acres of beautiful greenery and pedestrian friendly paths you can step back away from the hustle and bustle of city life. Bring a large blanket, a picnic basket, enjoy the weather, engage in conversation, learn about each other, and then depending on your mood choose from the three nearby museums to go appreciate: The Adler Planetarium, the Shedd aquarium, or the Field Museum.

10. Chicago Botanic Gardens

Enjoy a more active date. Go on a bike ride along one of the bike paths in Chicago, which lead to the Botanic Gardens. Several bike trails in the Chicago area lead to the Gardens and allows bikers to literally “stop and smell the roses” among many other flowers. Once you’ve reached the gardens you can park your bikes and have a nice walk with each other among the Japanese gardens full of bonsai trees or learn about edible gardens and walk away with some seedlings for your own homes. If you love nature and enjoy being active, this is definitely a date winner.