180+ Unique Chicago Date Night Ideas for Fun Couples

Lauren LoveFebruary 14, 2022Last Updated: September 15, 2023

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A unique Chicago date night by the river downtown

The Best Chicago Date Night Ideas for Fun Couples

If you’re struggling to find new and exciting ideas for your next Chicago date night, you’ve arrived at the perfect place. Datingforthesoul.com has gathered an extensive list of suggested date night ideas for the greater Chicago area. From cooking classes to go kart racing, it’s all here. We’ve done all the heavy lifting and research for you. Everything you need to plan the perfect date night is all in one place.

Plan a Unique Activity Date

Caucasian couple painting art on a unique Chicago date night

Activity dates are great for socializing and bonding with your mate on a different level. They’re interactive and allow room for showcasing talent or any other skill previously not revealed to your mate.

Cooking classes are a great way to spend time with your special person and perhaps show off your skills. Sign up for a cooking class at Sur La Table and prepare a special meal with other couples on a group date night. It’s simple yet fun, and there’s no grocery shopping involved (which is always a plus).

If cooking isn’t your favorite thing to do, register for a paint and sip class at one of Chicago’s many public art studios. Painting with a Twist allows visitors to sip on their favorite glass of wine while learning how to paint in a social setting. Snacks and other light food are permitted as well. It is highly suggested to make reservations in advance to ensure your spot is covered for the evening. There’s nothing worse than arriving at a venue and missing out because you didn’t plan properly.

Check out these other activity date night spot suggestions:

Plan an Exciting New Adventure

Two Caucasian men riding in go karts on a unique Chicago date night

Tired of boring, quiet dates with limited fun and excitement? If you’re a couple that craves adventures and loves to try new things, an adrenaline pumped date might be the best option for you.

Soar to new heights with your love on a skydiving date high in the clouds. There’s no higher thrill than jumping out of an airplane. Experience tandem jumping with a trained professional at Skydive Chicago and plunge toward Earth in safe hands. Freefalling lasts for approximately 60 seconds followed by a gradual descent that lasts 5-7 minutes.

If plummeting towards open land isn’t your thing, head over to iFly Indoor Sky Diving for a simulated experience inside of a wind tunnel. You’ll still have trained instructors to assist you, however you’ll only be a few feet from the ground rather than several thousands. It’s definitely a safer option for couples seeking a less risky thrill.

Here are a few other great adrenaline packed activities for your next date night in Chicago:

Head to the Bar for Date Night

Interracial couple sitting down at a restaurant on a unique Chicago date night

Bar dates are truly underrated. Some of the best date nights occur with a glass of good wine and appetizers. The atmosphere is easygoing, and expectations are super low for the evening. Sounds worse than it really is, but sometimes couples need a laid-back evening without worrying about the level of fanciness a 5-star restaurant requires. You can come as you are and chill.

Stop by The Violet Hour in Wicker Park for an artisanal cocktail experience you won’t forget. The ambiance is inviting, warm and filled with candlelit tables for the perfect romantic night out. This venue also offers cocktail classes with an advanced reservation. Virtual classes are additionally offered.

The Lazy Bird is a music and cocktail lounge located in Chicago’s Fulton Market District. Guests are serenaded with live music and over 52 cocktail options. The atmosphere is small; however, the vibe is larger than life in this quaint little piece of the city.

Here’s a list of our favorite bars and lounges in the Chicago area:

Sip on a Good Cup of Date Night Java

Cup of coffee with dates on a serving tray

Coffee dates are always a good option for couples looking to connect. Some of the most intellectual conversations occur over a cup of good java. The atmosphere is typically quiet, and the mood is just right for learning more about your date. Besides, who doesn’t love a cup of frothy cappuccino with a sweet, light flaky pastry on the side?

Take a peek at a few of our suggested Chicago coffee date night spots:

Indulge in Sweets with your Sweetie

Tasty dessert sweets displayed in a dessert shop window

Dessert shops are a sweet and friendly alternative to the typical date night scene. Skip the main meal and head straight for the sugar with your honey.

Perhaps one of the most well-known dessert places in Chicago is The Ghiradelli Ice Cream and Chocolate Shop. Their tasty chocolate squares are popular worldwide and have been delighting tummies since 1849. Not only do they offer delicious chocolates, but they also sell a variety of high-quality ingredients for milkshakes, coffee, hot cocoas and smoothies.

Check out these other top delectable destinations for your next unique Chicago date night:

Plan a Fast-Food Chicago Date Night

A plate of burger and fries on a unique Chicago date night

Fast food dates have traditionally received a bad reputation for being cheap and thoughtless. However, planning a date at a local fast-food joint can be the perfect date night spot to set the evening off right. Typically, fast food spots are the precursor for another fun date night activity such as the movies or bowling, etc. So, never underestimate the power of a quick burger and fries meal. It definitely serves its purpose.

Swing by Portillos on your next date night in Chicago for the best street food in town. Featuring Chicago-style hotdogs, char-broiled burgers and other succulent dishes, this fast-food stop will satisfy the pickiest of eaters. There’s something for everybody. Salads, pasta dishes, and desserts are additionally available.

Epic Burger is another popular burger joint in the Windy City. If you’ve never had a sandwich at this place, you are truly missing out. While their burgers are certainly the most popular menu item, they also offer chicken sandwiches, veggie burgers, and beyond burgers. More than enough to satisfy the needs of any couple on date night.

Take a look at these other fast-food spots for your next date night in Chicago:

Bond & Burn Calories at the Gym

A man assisting a woman doing push ups in a fitness gym

A couple who works out together, stays together. Well, that’s what they say anyway lol. Maybe it’s the “feel good” hormone released during workout sessions that keeps couples floating on cloud nine. Or perhaps the bond created after conquering a tough workout together. Nonetheless, gym dates are growing in popularity.

Many local gyms allow drop-ins for their weekly classes or allow members to bring a guest for the day. So even if your beau isn’t a member of the same gym, you can still invite them to spend time with you on your own turf.

Plan your next unique Chicago date night at one of these local fitness centers:

Spend a Day at the Lake

It’s no secret that Lake Michigan is one of Chicago’s main attractions. It’s also one of the best locations to spend time with someone you love. Spend time at one of the beaches located along the city’s shoreline or register for a dinner cruise at sunset. The possibilities are endless.

Navy Pier is a popular destination for tourists, however it’s also home to various local eateries and dessert shops. Additionally, it features several park rides, game attractions, and other fun activities. Perfect for your next unique Chicago date night.

Here’s a list of suggested lake dates:

Schedule a Chicago Date Night at the Movies

Couple sitting in movie theater seats holding popcorn on a unique Chicago date night

Movie dates are always a great idea. Not much planning is required, just pick a time and show up. However, the best thing about planning a night at the movies is the food. The days are long gone when popcorn and candy were the only options. Couples can now enjoy a full meal from the comfort of their seats. How wonderful is that?

Select any of these local movie theaters for your next Chicago date night:

Spend a Night at the Museum

Chicago is very rich in history and culture. That’s why we recommend scheduling a date at a local museum. Spend time learning the history of the region at the Chicago History Museum or explore endless isles of art at the Museum of Contemporary Art.

Check out these other great museums for your next unique Chicago date night:

Take a Walk in the Park

Couple at the park sitting in the grass by a lake

A walk in the park is the perfect chance for couples to connect with nature, and bond as a unit. It’s also one of the best ways to socially distance. The ongoing Covid-19 pandemic has forever changed our world. Therefore, if you’re concerned with being as safe and low risk in public as possible, plan your next date at a park.

Here are the most popular parks in the greater Chicago area:

Grab a Deep-Dish Pizza for Date Night

Giordano's Pizza on a unique Chicago date night

If you’ve lived in Chicago for any period of time, I’ll sure you’re already well aware of the best deep-dish pizza joints to frequent. However, we’d still like to briefly mention our preferred date night pizzerias.

Check out these awesome pizza spots for your next Chicago date night:

Make a Chicago Date Night Restaurant Reservation

Steak and fries on a plate at a restaurant

It’s no secret that the city of Chicago is a food lover’s paradise. The city is jam packed with great cuisine from all around the world. One could literally reserve dinner at a different restaurant nearly every night of the year and never eat at the same place twice. The options are endless.

If you’re into succulent steaks and rich sides, check out Steak 48, Eddie V’s or The Capital Grille. All venues deliver some of the most succulent and juicy steaks you’ll ever have. Not to mention, side dishes that will greatly satisfy your palate.

Summer House Santa Monica and Girl and the Goat provide an eclectic vibe, guaranteed to give off feel good vibes and good times. Their menu options are also rather delicious.

Here are a few other wonderful restaurants for your next Chicago date night:

Visit a Local Rooftop Venue & Inhale the Skyline

Classy Caucasian couple sitting down at a rooftop restaurant on a unique Chicago date night

Rooftops give off sexy vibes and a bit of enchantment. Plan a date at one of Chicago’s rooftop venues and start the night off right. The city skyline is perfect for romantic evenings and for couples seeking to spice up their relationships.

Choose any of the following rooftop venues for your next unique Chicago date night:

Tour the City of Chicago

Chicago is a city bursting at the seams with cultural diversity, history, and uniqueness. There are plenty of things to do and tons of places to visit. Therefore, why not be a tourist in your own city? Tours are not only reserved for visitors, but also for Chicago natives that want to learn more about the city they call home.

If you’re a foodie eager to learn more about the city’s food scene, check out one of Chicago’s popular food tours. Chicago Food Tours, Chicago Pizza Tours, and Secret Food Tours all provide a rich history of the city’s best eateries along with multiple chances to taste different foods.

Mob lovers and fanatics can check out the Chicago Gangsters & Ghost Tours. Chicago is well known for its mobster history, so why not take a step back in time with some of the most infamous crime bosses with your boo?

Check out these popular Chicago tours:

Hopefully you’ve enjoyed this master list of unique Chicago date night ideas! Spending time with your significant other in the city should always be fun, enjoyable and unique!

Come back to Datingforthesoul.com for all the latest dating and relationship advice!

Also, if you’re single and ready to mingle, join the free singles database with our preferred matchmaking agency here!

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