Chicago Date Ideas: 20 Best Date Night Spots


Last Updated: June 6, 2024

Dating Tips

With these exciting, creative Chicago date ideas, you’ll see why the Windy City is such a fun place for romance! We have something on our list for the food lovers, the moviegoers, the athletes, and anyone who wants a taste of the quintessential Chicago charm, so let’s get started!

Chicago date ideas for foodies

Looking to bond over a delicious meal? Here are a few recommendations for next-level dining in Chicago.

1: North Pond

There are many things that make an evening at North Pond romantic: the view of the Chicago skyline, the intimate and warm ambiance, and of course, the incredible Michelin star food.

North Pond is well known around the city to be the ideal special occasion restaurant, so make sure to book your reservation early.

2: Library Bar

Looking for a taste of prohibition-era Chicago? Library Bar is a speakeasy that will bring you right back to that classic bootleg-cocktail era. It’s located in the basement of the Gilt Bar in River North, and we can say that they’ve really stuck with the speakeasy spirit. For one thing, you can’t stroll right into the Library. You have to ask for admission and be escorted to the unassuming basement entrance. Be aware that it’s only open from Thursday to Saturday after 6 pm.

The Library is known for its traditional cocktails, but the food is also very good here! So, you can stop in for a drink before your dinner reservations or make it a full date with a meal.

3: Cindy’s Rooftop

No matter the time of year, a rooftop bar is an ideal date idea. And Cindy’s is the place to be, no matter if you’re clinking summer cocktails in July or cozying up with something off of their extensive spirits menu during winter. The views are incredible, the terrace is all-season, and you’ll also enjoy the changing menu from Executive Chef and former Top Chef contestant Kaleena Bliss.

Dates for the cultural couples

Looking for date ideas that will spark discussion and inspire your artistic side? Try out these date ideas for cultural activities in Chicago!

4: The Art Institute of Chicago

If you live in Chicago, you’ve probably visited this museum plenty of times. But, seeing it with fresh eyes alongside your special someone can give you a totally new experience! Plus, the Art Institute also offers a changing calendar of events which will make your visit even more special. Take a look at upcoming Gallery Conversations and Garden Parties to level up your next date.

5: See the Chicago Symphony Orchestra

The Chicago Symphony Orchestra is an important part of Chicago history! Since its founding in 1891, it’s played a key role in the city’s cultural scene and it continues to hold its place as one of the best orchestras in the country and around the world! Concerts in this gorgeous setting are sure to wow your date.

The key is to find an event that you know your special someone will love, whether it's an evening of classical music or their favorite film screened with live orchestral music!

6: Picnic and a movie at the park

Movies in the Parks is a local-favorite activity that you should definitely put on your date idea list! Whether you want to enjoy a Hollywood classic, a nostalgic 80s film, or something modern, there’s a screening you and your date will be sure to enjoy.

Make sure to pack a picnic with some snacks and beverages and load up on the picnic blankets for extra coziness.

These events take place all over the city during the summer, so check in with your local park for more info on screenings.

7: Broadway in Chicago

If you know that your date is a fan of the theater, they’ll love the chance to see what’s popular right now on Broadway in Chicago. You might take them to see a classic like the Book of Mormon or something fresh and new. Either way, catching a live performance will be an unforgettable date night!

Chicago date ideas to get you moving

If you and your date are active people, you can’t go wrong with an active date! Here are a few date ideas for the sports-minded:

8: Go for a jog in Grant Park

If you’ve bonded over your shared love of jogging, then a run through Grant Park is in order! This is one of the most picturesque running areas in the city, and because it’s nice and flat, you’ll be able to chat through your relaxed jog together.

Make it extra special by planning to enjoy a coffee or lunch together afterwards!

9: Kayaking on the Chicago River

Another fun warm-weather activity is kayaking on the Chicago River! It’s a wonderful way to get a different perspective of the city while getting in a great workout. There are a few different kayaking companies that you can use to organize your adventure, and you and your date can opt for a guided tour or hourly rentals.

10: Ice skating

Too cold for jogging or kayaking? Then, consider a romantic ice-skating date instead! There are many places to skate in the city, but the most well-loved is the McKinley Park Skating Rink. This seasonal rink located in McKinley Park is well-maintained and not too crowded, giving you a more laid-back and comfortable skating experience!

11: Take a stroll through a Chicago Street Market

Chicago has some of the best street markets in the country, with fresh produce, friendly community vibes, live music, and more! No matter where you are in the city, you can find a nearby street market throughout the warmer months. And, simply strolling through, maybe with a coffee in hand, is a romantic way to spend the weekend!

Classic Chicago date ideas


Maybe your date is coming from out of town and you want to give them the full Chicago experience! These date ideas are quintessential Windy City activities that will make them love it here:

12: A movie at Music Box Theatre

This classic Chicago theater has been around since 1929 and after a few renovations, it has the perfect balance of original charm and modern amenities.

What locals love about the Music Box Theatre is that it plays exclusively indie, cult, foreign, and classic movies. So, you and your date will certainly have plenty to talk about no matter what is on the line-up!

Don’t want your date to end after the movie? Head to the Music Box Lounge or garden patio for a cocktail or beer!

13: Bowling

Bowling is such a classic date idea, and Chicago has plenty of locations for you and your date to knock down some pins!

Depending on your style, you might opt for one of Chicago’s larger and more modern bowling alleys, such as the 40-laned Waveland Bowl complete with a billiards room and arcade, or the more classic spots like Southport Lanes.

14: See a local team

Sports are big here in Chicago, which means that no matter what time of year you’re planning a fun date, there’s bound to be a sporting event to enjoy! You might, for instance, take your baseball-loving date to see a Cubs or a White Sox game. Or, head to the United Center for a Bulls basketball game. If football is more your speed, you can get tickets to a Bears game. Or, check out the Chicago Blackhawks (hockey) or Chicago Fire (soccer) for even more options.

As long as you root for the home team, you can’t go wrong!

15: Take in the music at the Jazz Showcase

Chicago takes pride in its influence on jazz history, which means that this is a great city to see a jazz show! And what better place to take in the unique style of Chicago jazz than the Jazz Showcase? Often referred to as the place “where jazz lives in Chicago,” you can enjoy a show in the same place where musical greats Freddie Hubbard and Dizzy Gillespie once performed. There are musical guests throughout the week, so you’ll be able to see someone amazing no matter when your date is planned.

Sweet Chicago date ideas


Looking for date options that feel right out of a rom-com? Take a look at these classically sweet Chicago activities:

16: Garfield Park Conservatory

Nothing says sweet like thousands of floral-scented plant species on display at the Garfield Park Conservatory. A stroll through the 8 indoor display gardens and 10 acres of outdoor gardens is about as romantic as we can think of! And, you can even sweeten the deal by attending one of the conservatory’s popular events, including beekeeping classes, bonsai workshops, and more.

17: Swan Boat ride

Humboldt Park is such a lovely place to spend an afternoon paddling around in a swan boat with your special someone. You’ll have plenty of opportunities for sweet and silly selfies, and you’ll get great views of this popular park. If you have time after your romantic swan boat ride, make sure to stop in at the National Museum of Puerto Rican Arts and Culture housed within the iconic stables and receptory building. There’s also a cafe next to the swan boat rentals if you’re looking to add a meal to your romantic outing!

18: Enjoy an Original Rainbow Cone

Treat your sweet date to one of Chicago’s most famous sweet treets: the Original Rainbow Cone. This delicious Chicago tradition, which is a multi-flavored ice cream cone with sliced instead of scooped layers, has been around for almost 100 years. The OG Rainbow Cone comes with orange sherbet, pistachio, palmer house (vanilla with cherries and walnuts), strawberry, and chocolate. But, you can order other sliced stacks, such as minty city or orange dream.

Chicago dates to relax

Maybe after seeing all of the active and exciting date ideas on our list, you’ve decided that you want a date that is more on the relaxing and rejuvenating side! Take a look at these uniquely zen ideas:

19: AIRE Ancient Baths Chicago

AIRE takes the concept of relaxation all the way back to ancient Greece with soothing thermal baths! Although you can find locations in cities all over the world, you’ll love that AIRE Chicago pays homage to the historical architecture of our city in their candle-lit renovated River West factory. For ultimate relaxation, we would suggest booking a massage with your romantic spa experience.

20: Take a pottery class

If you’ve never taken a pottery class, get ready for a fun and relaxing learning experience with your special someone! Working with clay has a soothing effect, and with your hands busy, you’ll have plenty of phone-free time to sit and chat.

There are many excellent pottery studios in Chicago where you and your date will learn the basic skills of ceramics, and you’ll even create a keepsake that will remind you of your special evening together!

Chicago is full of amazing date options!

No matter if you’re going for romantic, active, classically sweet, or quintessentially Chicago-esque, there are so many options for your next date! Here are a few final words of advice for planning your perfect date in the Windy City:

  • Pay attention to the weather and season. Winters creep up fast here, and when they do, many of the summer activities shut down for the season.
  • Stick to a neighborhood. You don’t want to spend your date night stuck in traffic. So, if you have multiple stops on your mind, such as drinks, dinner, and then a movie, make sure they’re all in the same neighborhood.
  • Enjoy the Chicago charm. Dating in Chicago can be fun, exciting, and ever-changing. So, make it a point to plan out a range of different activities to experience the full spectrum of what Chicago has to offer.

So, which of these Chicago date ideas will you try first?

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