The Most Stylish Date Spots in Chicago & What to Wear
One thing I love more than playing dress up is sitting down for a good meal! And Chicago has it all: charm, architectural marvels, and some of the best food and cocktail spots in the world. My husband and I started having weekly, and sometimes daily, date nights and date days as a way to make sure we’re always spending quality time together. So, whether we head out for a romantic brunch, a sophisticated afternoon of cocktails, or a cozy and intimate experience, we look good while doing it.
To help you choose food and outfits that are unforgettable, I’ve rounded up some of the best daytime date spots in Chicago—along with style inspirations from some of the most talented designers featured on Letty Sparrow.
1. Cindy’s Rooftop | Visit Cindy’s
The vibe: Elevated elegance with breathtaking skyline views overlooking Millennium Park.
What to wear: Go for an effortlessly chic look with a flowy, bright dress by Sujata Gazder. Pair it with timeless drop earrings from Maancy to highlight your refined style.
2. The Godfrey’s I|O Lounge | Visit The Godfrey
The vibe: A stylish, year-round rooftop with a retractable roof and craft cocktails. What to wear: Opt for sleek sophistication with a well-tailored collared halter dress from Shernett Swaby. A structured handbag by Styled By Demetra completes the look, making sure you turn heads with understated elegance.
3. Cabra | Visit Cabra
The vibe: A vibrant Peruvian-inspired rooftop with colorful cocktails and shareable plates.
What to wear: Bring the boldness of Peru into your outfit with a statement piece—perhaps a vividly patterned dress by Maria Pinto . Complement the look with a handcrafted headpiece from Azeeza.
4. Storyville | Visit Storyville
The vibe: A French Quarter-inspired lounge with chic cocktails and Southern flavors. What to wear: Channel NOLA charm with the “reckless innocence” with the unisex Sorebet Shoe by Yohance Lacour.
5. The J. Parker | Visit The J. Parker
The vibe: A rooftop bar atop the Hotel Lincoln offering 360-degree views of Lincoln Park and Lake Michigan.
What to wear: You and your date can match in the versatile Exclusive NICZKA Design House jacket over sleek silhouettes.
6. Park Grill | Visit Park Grill
The vibe: Millennium Park’s signature restaurant with a lively patio atmosphere.
What to wear: You can’t go wrong with the Vegetable Tanned Leather Apron by Production Mode paired with a relaxed tee and ankle boots keeps you warm while exuding downtown-chic vibes.
7. Green Mill Cocktail Lounge | Visit Green Mill
The vibe: A legendary jazz lounge with a vintage speakeasy feel.
What to wear: Step out in a fresh, classy warm-up jacket by Always Greyvi and match with your partner in a pleated mini skirt for a sexy evening.
The Final Touch
No matter where your Chicago daytime date takes you, style is a reflection of confidence. Elevate your look with thoughtful details from the best of Chicago’s local luxury designers, and let Letty Sparrow guide you to your next unforgettable outfit.
Which of these date spots are you trying next? Tag us in your photos and let us know your go-to stylish date look!
