We’ve reached the time of year in Chicago where the weather can either be great or awful. Case in point - we went from a week of beautiful 60 degree and sunny days to 20 degrees with a bitter wind back up to the 50s accompanied by abnormal tornado weather followed by a snow day. Needless to say, Chicago is on crack and needs to make up it’s mind. Date night is easy to plan when you know the weather is going to be gorgeous or even awful. But when it’s a toss up, it’s not so easy. We have rounded up a few restaurants that provide an exceptional experience indoors while the outdoors are a gamble. Innovative cocktails, gorgeous city views and decadent dishes make for an ideal date night. This list should take you through the rest of winter until patio season begins and the city comes alive once more.

Bavette’s Bar & Boeuf | 218 West Kinzie Street
Get a little closer in the dim lit, European-style restaurant. A little on the smaller side, Bavette’s is an intimate space to enjoy a table for two. Bavette’s originality stands out with unique and extravagant offerings like their seafood towers and decadent desserts made in-house. We suggest the Chocolate Cream Pie. What’s even greater about Bavette’s is the variety of price points and menu options. From traditional salads to elegant and classic French cuisine, you’ll find anything from a Classic Ribeye to Roasted Bone Marrow. Oh...and nothing is simple about any of their dishes. Each one stands out in its own special way.

Blackbird | 619 West Randolph Street
My first experience with Blackbird was at a friend’s wedding. After an outdoor ceremony in August, we made our way to this West Loop gem for the best reception meal I’ve enjoyed. You’d expect nothing less from Paul Kahan and Ryan Pfeiffer. Together, they’ve created a restaurant that brings innovation and Midwestern cuisine together in a way that foodies and non-foodies alike can appreciate. The sleek, modern restaurant design provides a sophisticated atmosphere perfect for a first date or night out early in your relationship. We recommend the caramelized Brussels sprouts, and aged duck breast but don’t be surprised if they’re not on the menu when you stop in. Blackbird works seasonally with its ingredients so a menu change isn’t uncommon throughout the year.

Celeste | 111 West Hubbard Street
Inspired by a classic American cocktail bar, like the other restaurants on our list, Celeste is a unique experience all it’s own. From plush seating to marble tables and a vintage-style garden patio, it’s a sophisticated, chic experience couples out for a night on the town dream of. Stop in for a cocktail or glass of wine and move on to dinner. With cocktail names like She’s New In Town and Mr. Untouchable, conversation will never run dry. Indulge in dishes like the Steak Frites or Fried Chicken. You won’t be disappointed at these classics. Looking for a place to keep the conversation going after hours? Celeste’s late night pub menu has everything from a Kale Salad to French Fries and they’re open til 4am Tuesdays to Fridays and 5am Saturdays.

Cindy’s Rooftop | 12 South Michigan Avenue
Cindy’s Rooftop is in the Chicago Athletic Association Hotel. Open during the warmer months and enclosed when the weather is uncooperative, Cindy’s offers some of the best views of Chicago. Overlooking Millennium Park and the lake, the restaurant is famous for drink shots and selfies with the view in the background. The view, however, does not outshine their menu. Known for an innovative and creative cocktail menu, Cindy’s is the type of place where time flies. You stand at the bar for an hour or more and find your way to a table after a few glasses of wine. Next thing you know, three hours have passed. Believe me when I say I speak from experience. While they’re known more for their brunch, I must give a shout out to their dinner menu. From charcuterie plates that rival those in France to savory entrees like the Pan Roasted Duck Breast, your taste buds will be tantalized. The service is incredible, the atmosphere electric and the experience priceless.

Photo c/o Cindy's at the Chicago Athletic Hotel Association

Spiaggia | 980 North Michigan Avenue, 2nd Floor
For a hearty and luxurious Italian experience, Spiaggia offers a combination of classic Italian dishes and twists on old classics. Regardless of your final decision, anything you order will leave you satisfied and satiated. Choose between a five or eight course menu for the tasting menu with or without accompanied wine pairings. The a la carte menu features a selection of pastas, entrees and starters. Looking for something a little lighter and casual? Stop into their lounge for the Bar Menu. They serve a variety of cocktails and impressive wine list with a selection of dishes like the Bolognese which I must recommend.

Photo Credit: Galdones Photography via Spiaggia

The Dawson | 730 West Grand Avenue
Casual meets sophistication at the Dawson. This is the type of restaurant where you’ll find ladies sipping wine or cosmos and gentlemen, classic Manhattans or craft beer. I recommend the Dawson to everyone for every occasion. Their menu changes seasonally and they have a beautiful patio during the warmer months. I have yet to be disappointed by the service, atmosphere or food. I recommend the Frites, Kale and Farro Salad, Dawson Burger, Scallops and Warm Brown Butter Sundae. The Dawson is a fantastic spot for a double date, group date, first date or a night out away from life.

The Village | 71 West Monroe Street
A small taste of Italy sandwiched between skyscrapers, The Village is one of three restaurants part of The Italian Village. The restaurant opened in 1927 and has been a favorite of my family’s since before I was born. Reservations book fast for this popular Italian spot, especially because it’s prime real estate in the Theater District. Since I’ve been frequenting this restaurant a few times a year since I was born, I’ve made my way around their menu which has pretty much stayed the same. The Chicken Parmigiana is delicious as well as the Lasagne, Cannelloni, Manicotti, Agnolotti and Prime Beef Carpaccio. The restaurant is dimly lit and designed to feel like a restaurant in the heart of Italy. Romanesque statues stand tall throughout the space with red leather booths and crooners in the background.

Do you have a date night recommendation in the city? Tell us in the comments below.

7 Spots For Date Night In Chicago

Home Blog

Contact Subscribe