Date Night! Whether you’re in the mood for romance, great cocktails, delicious food, or a little friendly competition….I got you covered! I’ve been on some fabulous dates and the spots I’ve listed below are memorable to me because of them. Of course, I’m not able to squeeze in every date spot, so if you’re willing to share make sure to comment what spots you and your boo frequent. 🙂
Shall we begin???
1721 W Division Street, Chicago IL
When it’s my turn to come up with a date spot this is the place I choose. Bordel is a SEXY speakeasy located on the top of the bar Black Bull in Wicker Park. I think I’ve probably taken every guy I’ve dated here and I don’t plan on stopping anytime soon. LOL. Cocktails are creative, ambience is red and sultry, and if you pick the right night (follow them on social media @bordelchicago) you can take in a burlesque show.
Tip: Like every speakeasy this place can be tricky to find. Instead of making a left into Black Bull head on up the stairs and enter the door on the left.
The Esquire Champagne Room
58 East Oak Street, Chicago IL
I’m a sucker for any place that pays attention to detail and ups their interior design game. The Esquire Champagne Room looks like a bottle of fine wine! The furniture screams seductive and of course the wine game is on point. Located upstairs from Del Frisco’s Double Eagle Steakhouse is a cozy spot with a wine list like no other. Have dinner at Del Frisco’s and then have sommelier/and resident wine director Amy Lutchen help you make a wine selection. Your date will be super impressed with this elegant spot. Cheers!
1604 W Chicago Avenue, Chicago IL
There’s two locations now, but my favorite location is the one located on Chicago Avenue. I went on one of the best dates of my life here. Sure it was the guy….but it was also the old world elegance that did it for me. You can’t help, but to fall in love with this beautiful restaurant with lush interiors and jaw dropping chandeliers. There was a Dj the night we went and the alcohol slushies we had were very unexpectant….just like everything on the menu. The flavor combinations and well execution of the cocktails will have you coming back for more!
613 N Wells Street, Chicago IL
So many people reach out to me for recommendations for their anniversaries, birthdays, special occasions, etc… That’s why I decided to put together a go to date night spot list. When I inquired what are some of you guys favorite date night spots, I was recommended to check out Blind Dragon. Well make sure you go in with your eyes wide open because this is a beautiful spot!! Blind Dragon is fairly new on the scene. Shhh…it’s a chain (locations in Los Angeles and Scottsdale), but it sure doesn’t feel like it. If you like to enjoy your craft cocktails in a beautiful setting then this is the place for you. For those of you that like to enjoy your craft cocktails while singing off key….well there’s also a private Karaoke room you can book. Make sure to share your music videos with us online though! LOL
111 W. Wacker Drive, Chicago IL
I told you I would cover all types of date night spots! I think every relationship needs a little healthy competition to get the blood flowing. I had so much fun on a date here competing in a game of darts. This isn’t just for advanced dart throwers, Flight club is a social darts spot. I was a newbie, but quickly caught on to the game and won a few rounds! Even better the food was delicious. Chef Rick Gresh has an awesome selection of what I would call high end bar food and Peter Vestinos is a wizard with the cocktail list.
230 N Clark Street, Chicago IL
Another great spot to get competitive at is Acebounce. I’m far from being a pro at ping pong, but me and my date had so much fun playing against each other (especially after a couple of cocktails). Food was delicious, there’s plenty of ping pong tables, and I like at night they get psychedelic with the lights and the ping pong balls light up. You can have a “ball of romance” at this joint. Get it?!?! 🙂
Moxy Chicago/Zombie Taco’s
530 North Lasalle Drive, Chicago IL
Do you prefer to play your games sitting down? Well my next date spot will help you guys relive your youth. Bar Moxy and Zombie Taco’s offers guests tons of board games to play. We saw double dates taking in a game of monopoly, Uno, candyland, and Jenga. Mix some taco’s, with some cocktails, with some decent music and you have a fun and enjoyable date night. Have to mention I absolutely loved this Drake pillow they had on display.
Chicago Helicopter Experience
2420 S Halsted, Chicago IL
Ready to fly sky high with your date? Well how about a romantic helicopter ride with the beautiful skyline of Chicago as the backdrop. I’ve been able to enjoy the helicopter tour, but I sure would love to go back and experience the ride on a romantic date one evening (hint hint…LOL). There’s nothing to be afraid of. My ride experience was completely smooth and it was so fun to see the wonderful architecture of Chicago up close and personal. I would suggest doing a sun set or night tour. Our city with the lights on is absolutely gorgeous!
5311 S Lake Park Avenue, Chicago IL
Ready to venture a little out of the downtown area? Head on over to Hyde Park and check out The Promontory. There’s always various events going on, so make sure to check the websites event page. I remember one of my last dates here we checked out a series on Monday night called “The Corner series.” For a $5 entrance fee we got to see Sam Trump play live jazz music. Not bad for a Monday night and it was in such an intimate setting.
875 N Michigan Avenue, Floor 94, Chicago IL
Wanna head back to the city and play tourist for a day? Check out the 360 Chicago! The views are amazing and it’s worth it to try the tilt ride at least once. The tilt is pretty self explanatory…your 94 floors up and you TILT above the skyline (indoors of course). So much fun, but definitely not for the faint of heart. At the 360 there are also yummy cocktails to choose from with cute neighborhood names. My advice is to go early evening. You get to enjoy the beautiful sunset, but stick around for the city lights at night.
IO at The Godfrey Hotel
127 W Huron, Chicago IL
I can’t help it…I put IO at the Godfrey Hotel on all of my lists. No matter if it’s date night, girls night, bday celebrations…I’ve done it all at IO. Located on the fourth floor of the Godfrey Hotel, IO has some amazing views and a super trendy set up. If you wanna impress your date on a budget stop by for their EXCELLENT happy hour Monday – Thursday from 3pm to 6pm and from noon to 3pm on Fridays. Happy hour specials include $5-$7 food items and cheap drink specials as well. I have been on sooooo many dates here and definitely recommend checking this spot out.
111 W Kinzie Street, Chicago IL
Untitled has been around for a minute now, but this is still one of my favorite spots. This is the spot that first started my love addiction of speakeasy’s. Located behind an unmarked door on Kinzie Street, (next to the CVS) is…Untitled. 10,000 square feet of super swanky space! There’s three different rooms and I’ve had dinner in all of them. Enjoy live performances, well crafted drinks, and a vibe like no other. I like that I always feel comfortable here whether I’m dressed up or down. If it’s your first time I would suggest the tasting menu. It’s a little pricey, but the quality of food warrants it.
676 N Orleans Street, Chicago IL
At one point I wanted to go on nothing but speakeasy dates. Even till this day speakeasy’s are just so super sexy and I love the hidden away aspect. My first time at The Drifter was fun!! It’s hidden underneath the Green Door Tavern. I will warn you I know some people have mix experiences here because they charge cover during shows and a lot of times do not alert you of this. There are live shows, great drink list (which is displayed on tarot cards), and this space is tiny. Small bites are served, so don’t come here if you’re super hungry.
The Front Room
844 W Randolph Street, Chicago IL
I haven’t been on a date (just yet) at the Front Room, but I have been and mentioned to my friends this would be a great date night spot. There were so many couples there engrossed in conversation underneath the dimly lit room. A live Jazz band was playing in the background and love was in the air!! Not a huge menu, but a little something for everyone. I went with the Jambalaya and saw quite a few items I want to try next time some lovely gentleman wants to take me back.
660 W Lake Street, Chicago IL
I’ve been to Moneygun on several occasions and went recently for a date during the week night. It reminded me why I love this place so much. Unpretentious, great drinks, great music, and an all around good time. It also has that speakeasy vibe I love. My recommendation is to order a cocktail (tell the bartender you want it set on fire….you’ll see), and enjoy the delicious meatball dish. You’ll thank me!
So how’d I do!?! I was so worried about doing a date night spot list because Chicago has soooo many great spots to offer. I couldn’t possibly fit it all in….like Jazzin at the Shedd, tacos at Barrio, drinks at apogee lounge, or violet hour. You’ll just have to keep exploring with your honey on your own!! I plan on trying to put together an updated list in the near future….so if you have a spot you think we should know about hit me up at Tavij@chiataglance.com. Hugs n kisses! 🙂
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