‘Romantic’ might not be the first adjective that comes into your mind when you think of Chicago, a city famed for its deep-dish pizza and gangsters. But amongst the obvious cultural landmarks, there are plenty of fun and unique things for couples to do.

Nestled amongst the impressive architecture, you’ll find atmospheric bars, restaurants and live venues just waiting to be explored as part of a romantic day out.

As well as an impressive food scene, Chicago has a long-standing reputation as one of the best cities for live comedy and music. If your partner’s a shopaholic, there’s plenty of upscale and boutique stores to satisfy any cravings for retail therapy.

Whether you’re looking for a more laid-back date, or something to sweep them off their feet, we think you’ll find a romantic date to suit the individuality of your relationship from our selection below.

Read on to find out our romantic date ideas in Chicago!

Gourmet Chicago Dinner Cruise 

What could be more romantic than gently gliding along Lake Michigan, looking at your partner across the table as you enjoy a gourmet meal together?

As you and your partner board the ship, stop a moment and meet the captain and crew. Next, enter the boat and discover an elegant dining room. While on board you will be served a delicious three course meal, indulge in creative appetizer, entrees, freshly prepared desserts and an array of award-winning wines. After your meal, enjoy a cocktail on the outer deck while gazing at Lake Michigan.

You will cruise along the Chicago Lakefront to the Museum Campus enjoy the world-famous skyline, from the Willis Tower, to the John Hancock Center and the Shedd Aquarium. After taking in the stunning views, head inside to the dance floor and twirl your night away to the music.

We think this unique cruise will have the both of you grinning from ear to ear by the end of your adventure, and feeling closer than ever!

Take A Cooking Class at The Wooden Spoon 

Cooking classes are a fun and romantic way to bond, and there’s no venue in Chicago more romantic than The Wooden Spoon. Overlooking a quaint back garden adorned with water features, trees and flowers, this atmospheric cooking school is the perfect place to while away an evening with your partner, learning to create new dishes together with the help of an expert cook.

Whether you want to learn to make pasta like a true professional or expand your baking repertoire, there are classes to suit every interest and skill level. If you’re a couple who loves to eat (and who doesn’t?) we think this is a great Chicago date idea.

Chicago Beer Tasting and Bar Tour

If you’re a couple who loves craft beer and discovering new brews, opt for this Chicago beer tasting and bar tour for your next date.

This Chicagoland Beer Tour begins when you meet with your friendly and knowledgeable guide in either Bucktown, Lakeview or the Loop.

From here your guide will escort you to four venues where you’ll enjoy generous samples of ice cold beer at each location. Carefully selected for their contribution to Chicago culture, each venue will highlight not only mouth-watering brews, but also something unique in its own right – whether that be menu items, décor and entertainment, history or the best selection in town.

Walk Through The Botanic Garden 

Nothing could be more peaceful than strolling through a tranquil garden with your partner, and admission to Chicago Botanic Garden is free, making it the ideal low-cost date idea.

Here, you’ll find a myriad of different perfectly preened displays of nature just waiting to be explored. In the height of summer, enjoy sun-drenched flower-filled gardens that look like a romantic postcard. In the dead of winter, stay close and explore the beautiful snow-laden landscapes together.

No matter when you attend, there’ll be something eye-catching to see!

After Dark at The Adler 

The Adler Planetarium isn’t just for kids!

This 21+ exhibit invites starry-eyed adults to admire the Planetarium’s attractions whilst enjoying extra entertainment and drinks. Exhibit themes vary from month to month, so you’ll always get a new surprise.

If you and your partner are interested in astronomy, or just looking for a unique activity to fill a chilly Chicago evening, this unusual outing will do the trick.

Improv Show at Second City 

Are you comedy fans?

Improv is fast becoming recognised as an essential part of comedy; after all, so many comedic stars got their start making stories up on the spot at improv classes across the country.

Second City Chicago is one of these respected institutions, and has seen national treasures of comedy cut their teeth – including Steve Carell, Tina Fey, Amy Poehler, and Mike Myers. Must be pretty good, right?

Surprise your partner with a gut-busting comedy show that changes every evening. You never know what you’ll get, but you know your face will hurt from laughing by the end of the night, as actors onstage unfurl a bizarre narrative in real time, featuring one-of-a-kind characters made up in the blink of an eye.

Comedy fans will not want to miss this side-splitting date idea!

Have A Cocktail at a Rooftop Bar

Chicago natives will know the city is famed for its rooftop bars. With incredible sprawling views of impressive architecture and cocktails shaken up by expert bartenders, a laid-back rooftop drink is the ideal recipe for a low-maintenance date that your partner will love.

There’s no shortage of bars to choose from, so pick your poison! Joy District features grass-covered walls and twinkling lights, perfect for an evening tipple, whereas the minimalist rooftop of The Godfrey Hotel would suit those looking for a sophisticated atmosphere. Streeterville Social serves laid-back, relaxed vibes for those looking to kick back with a cocktail or two.

These are just a few examples, so take your date along to any of Chicago’s huge offering of rooftop bars to impress them with views, drinks and atmosphere!

Catch A Show at The Chicago Theatre 

A night out at the theatre is a classic date idea for a reason, so treat your partner to a one-of-a-kind show from Chicago’s most famous live venue. Whether you want to enjoy a play together, dance to your favorite band, or giggle your way through a comedy show, the Chicago Theatre’s impressive roster of live events is always updating, so there’s no shortage of great things to see!

Bike Across The Chicago Lakefront Trail 

If you’re strapped for cash, a bike ride across the Chicago Lakefront Trail makes for a budget-friendly date idea.

Hop on your trusty bikes together and set out for some endorphin-boosting exercise while taking in stunning views. Zooming under tree-hugged bike paths, you’ll pass some of Chicago’s most desirable beach front views, and get a great workout while doing so.

To add an extra special touch to this fun idea, why not bring a bottle of wine and some snacks along with you to stop for a riverside picnic? Great views, company, food and fresh air… dates don’t get much better than that!

Admire The View from 360 Chicago Observation Deck 

I think if there’s one thing we’ve established during this article, it’s that Chicago has some stunning views. Whether admiring from a rooftop bar or from an observation deck, the city’s impressive architecture is a sight to behold.

Take your date up high with this 360 Observation Deck experience. For a truly stomach-twisting experience, opt for the new ‘Tilt’ ride, which (safely) tilts participants over the edge of the building so they feel like they’re floating in mid-air!

If your partner’s afraid of heights, this may not be the greatest date idea for them. But if the two of you favor an experience that takes you up high over the city, treat them to the thrill of a lifetime!

Thanks for reading!

Thanks for reading our guide to unique date ideas in Chicago. We hope you’ve found the perfect fun, foodie, romantic, exciting or unique date idea from our list above.

If you’re still looking for romantic ideas to impress your partner, browse our full range of Chicago experience gifts here.

Got a comment, or a Chicago date idea you think we missed? Please feel free to leave a comment; we’d love to hear from you!