Chicago Date Nights, Fun Dinner Spots, Coffee 1st Dates, Anniversary Ideas; Where To Meet Singles In Chicago, Chicago Date Night Restaurants, Chicago Date Spots

Chicago is one of my favorite cities in the world to visit. I use any excuse to make it out there whenever possible.

Aside from the beautiful architecture, scenic views, energy displayed by folks on the first warm day of the year and never say no attitude, this city has a plethora of great date spots for date spots for all lifestyle and incomes.

Below is a list of date spots, fun date ideas and romantic things to do in Chicago for all sorts of occasions whether it’s a date night, first date or anniversary.

Related reading: Dating In Chicago


Romantic Date Ideas Chicago, Date Night Ideas Chicago, Date Night Restaurants Chicago

In the past 5 years, there have been a number of places that have surfaced around the area as well as existing businesses that have catered to a growing younger demographic of customers looking for something beyond a dive bars and steakhouses.

The influx of amazing restaurants, craft beer, mixology options, farm to table option and artisanal approaches has given Chicago a liveliness that few cities have.

City Wine, Chicago Riverwalk Summer Happy Hour

Fun Date Night Spots Chicago Date Night Ideas, Restaurant Tips, Downtown Date Ideas

As an online dating photographer and consultant, I have helped clients plan first dates to provide good first impressions. Here are a few of my favorite places around Chicago for dates and meeting singles. Scroll to the bottom of the page for other cities and stay tuned for more postings in the future.

Please note there are many places I recommend that are more unique, romantic – these are exclusively available for clients.


Gin bar with great small bites and beautiful antique chic interior. Pro-tip: fireplace in the back room.

Slightly Toasted

Can’t go wrong with coffee cocktails –  Sex and Caffeine cocktail with bourbon whiskey, pineapple rum, nitro coffee and egg white

Beatnik On The River

Boho chic environment with great views along the river. Great for drinks and or bites.


I love this place for people watching. The lay out is great and well you cannot beat their ‘Coffee’: caffeinated cocktail with coconut-date horchata, cold-brew coffee, Averna liqueur and arrack.

Second City Comedy Night

Easily overlooked but definitely worth a visit. There are few comedy clubs and shows I can recommend confidently anywhere in the world, this is one of them. 

Ace Hotel, Waydown Rooftop Bar

Hard to go wrong with any bar options at any Ace Hotel anywhere in the world;.

Hubbard Inn River North

Great place for cocktails and small bites. This beautiful interior is sure to impress any date.

Hopleaf, Andersonville

This Belgian gastropub has over 60 beers on drafts with a strong focus on Belgian beers and ales. For the beer lovers, this is a great spot to check out when in town. 

Green Mill Cocktail Lounge

This old school, cocktail lounge and jazz bar is a great place to listen to music and go back in time.  


Kingston Mines, Blues Bar

This classic establishment is a must to check out for blues and live music.


Three Dots and a Dash

This famous speakeasy tiki bar is exactly what Chicago needs. For something festive, fun and make you forget those cold winter days in Chicago, swing by.


The Drifter

Cozy, old speakeasy bar with a small cover charge.


Ciccio Mio

Beautiful, cozy, rustic Italian restaurant with intimate lighting and limited bar seating. Hard to get reservations but well worth it for impressing a date.


The Aviary

This cocktail bar is a great place to experience flavors and styles of cocktails for the true enthusiasts that appreciate craft, presentation and gastronomical techniques.


The Office, Downstairs below the Aviary

A more intimate, cozy cocktail bar and lounge.


Bar Siena

Fun, social restaurant and bar great for people watching, grabbing drinks or having bites at the bar.


Berkshire Room, ACME Hotel

Fun cocktail lounge, great for people watching and grabbing a drink or two.

Dating Coach Services - Men & Women

First date ideas, wardrobe, places to meet singles, body language, conversation/social skills, grooming, hygiene, hobbies, lifestyle choices, reducing biases, weeding out time-wasters and more. As seen in the NYT, Bumble.

Outdoor Fun Date Ideas, Chicago First Ideas, Restaurant Tips, Best Date Night Ideas

Architecture Boat Tour

A must for locals and tourists. It’s one of those things you can do more than once and never get tired of. Chicago has the most amazing skyline and architecture that this tour cannot be missed.

LondonHouse LH Rooftop Bar

My favorite rooftop in all of Chicago. The rooftop is sits at the bend of the river providing a straight shot view down the river and is perfect for sunsets.

Walk Around Navy Pier, Ferris Wheel

Ferris Wheel, games, scenic views and a beautiful walk makes this an easy but intimate date idea for those on a budget or those looking to get a little exercise in. 

Cindy’s Terrace, Athletic Club 

This place gets crowded quickly but the design inside is as beautiful as the views from the terrace. If you can’t find a seat or space, head downstairs for a beverage in their swanky, classic den featuring bocce ball, chess, card games, table soccer and more. 

City Wine, Riverwalk

This is the place to be when the weather warms up. Arguably one of my favorite places in the world to grab a drink when the time is right.

Chicago Café – Restoration Hardware

An immaculate place for brunch. This beautiful garden patio is the place to be on a warm Sunday for brunch.


More Chicago Date Ideas: First Dates, Fun Dates, Summer, Outdoors, Best Restaurants

Best Date Spots in Chicago According To An OkCupid/Yelp Study:

Best Morning After Brunch: Lula Café

No-Judgement Makeout Spots: Slippery Slope

Fitness & Wellness Dates: Urban Kayaks

Best Hotel Bars: Cindy’s Rooftop

Cheap Eats: 90 Miles Cuban Café

Photo Friendly Spots: Punch House

Spots That Spark Conversation: Adler Planetarium

Spots Where Drinks Could Turn Into Dinner: The Violet Hour

Best Themed Bar: Three Dots and a Dash

Additional Date Ideas, SF, NYC, Napa & more, Best Date Night Ideas, Restaurants


For Chicago Tourism, Views, Points Of Interests, Dating Night Ideas Chicago & Attractions 


About Eddie Hernandez

Eddie is a dating coach for men & women in San Francisco (clients in NYC, LA, Chicago, & beyond ), as seen in the NYT & Bumble). He helps w/ profiles, photos, wardrobe, messaging, date ideas, red flags, lifestyle choices, hobbies, grooming/hygiene, communication, social skills & offline efforts.