Date Nights, Happy Hours, Fun Casual Dinner Spots, Coffee Dates Anniversary Ideas + Places To Meet Singles In and Around Chicago, River North, Riverwalk, 1st Dates and More

Chicago is one of my favorite cities in the world. 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.

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

City Wine, Chicago Riverwalk Summer Happy Hour | Chicago Photographer

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.

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.


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

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.

Slightly Toasted

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


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.

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

For additional date ideas, check out my other date idea posts here:

About Eddie Hernandez 

Eddie Hernandez is a professional photographer specializing in natural, candid online dating photos. Featured in the SFGate, ABC7News, East Bay Express, Salon; contributor to Good Men Project, Plenty Of Fish and Meddle. In addition to photos, he provides guidance around app choice, bio optimization, messaging techniques, wardrobe advice and date ideas.

Dating Profile Critique

For those of you who are remote or virtual dating help and are looking for an online dating profile critique you can read more about my services here.

For other helpful online dating tips check out my blog for more helpful advice:

Online Dating Frequently Asked Questions (Photos, App Choice, Wardrobe, Messaging, Bios and More):

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