10 Best Date Ideas in Chicago

Though Chicago may not be considered the city of love, it sure does hold its own when it comes to endless date ideas. Whether it’s your first date or you’ve been together for years, there’s something in Chicago for every couple to enjoy.

If you’re looking for something adventurous, unique, romantic or just plain and simple, then read on to find out which of these 10 best date ideas in Chicago you’ll want to try next.

1. Catch a Game

In a serious sports city like this, watching one of Chicago’s home teams play is a guaranteed good time, win or lose. Grab a couple tickets, throw on your baseball hats and sneakers and head to the park, court, field or rink. Chicago is home to several professional sports teams for endless entertainment opportunities. Depending on the season, one game might be the obvious choice over another.

If you’re both baseball fans, you’ve got two teams to choose from: the White Sox and the Cubs. Both comprise a following of diehard fans. If you and your date cheer for opposing teams, then chances are this won’t work. We’re only kidding – sort of. You may opt for a different sport altogether in this case, but keep in mind tickets for baseball games can sometimes start as low as $20 each.

Though the Chicago Bulls’ dynasty may be over for now, they’re still good for entertainment even 20 years later. You can catch a Bulls game for as little as $40 a ticket. Plus it’s indoors, which is in itself a win if the weather lets you down.

The Bears are one of the NFL’s oldest and most treasured teams. Find something orange to wear and get ready to yell your loudest “defense!” chant to cheer them on.

Speaking of old sports teams, the Blackhawks are one of the NHL’s original six franchises and are loved locally. Plus, they’re the defending Stanley Cup champions. Hawks tickets can sometimes start as low as $35 each. If you’re lucky, you might even spot Hawks super-fan Vince Vaughn in the stands.

After the game, you and your date can hit up a brew pub for wings and beer to celebrate. If you didn’t get tickets in time, that’s no problem. There are plenty of pubs around the stadiums that are packed on game night. This can be almost as fun as being there in real life. These pubs have a great energy and atmosphere, and you’ll be sure to make friends bonding over your mutual love for the home team.

2. Build a Robot

This is a one-of-a-kind date night idea and it’s something totally unique to Chicago. For couples who like a bit of quirkiness and creativity, this is a must-do. Robot Date Night is one of the many events held by Robot City Workshop, a local business that specializes in putting on classes for robotic hobbyists, tinkerers and do-it-yourselfers.

Robot City Workshop started in 2008 with the goal of introducing robotics to the average person to show us all that robots aren’t just for nerds. On the contrary, everyone can find something to love about robots. What better way to help forge the bond of a couple in love than to have them build their own robot together?

There’s more than 12 different DIY kits to choose from. During the robot-building event, popcorn and beverages are delivered by – what else – a robot. There’s also a robot-themed movie that plays while you’re building for further entertainment. Plus, did we mention it’s BYOB? You and your date will also receive two free beers courtesy of Metropolitan Brewing Co.

This date night may be unconventional, but it’s also an adventure. The event occurs every week on Thursdays, Fridays and Saturdays from 7 p.m. to 9 p.m. Tickets must be purchased in advance and are available for $25 each, plus the cost of the kits and batteries.

3. Take a Cooking Class

If you really want to know how compatible a couple is, put them in the kitchen together. Preparing meals together is great way to bond and build your teamwork skills. Plus, it gives you and your date the opportunity to see the results of your hard work and enjoy it together.

The Chopping Block is another local business and date-night entertainment provider that’s entirely unique to Chicago. For the past 18 years, the Chopping Block has been delivering an exceptional experience from start to finish with its wide variety of cooking classes. Its focus is solely on education and making cooking fun.

There are different types of classes you can try, like interactive or demonstration classes. It also offers wine classes which teach about the fundamentals of wine tasting and pairing. This is a great date idea if the two of you share a love for wines.

Cooking classes occur all week and need to be booked ahead of time. Entry-level classes start at $50 per person.

4. Attempt Kayaking

If you and your date are more of the outdoorsy and adventurous types, then you might want to try kayaking. Kayaks are available for rental by the hour or for a full day. There are also guided tours and lessons available for all levels of skill and experience.

Just like robot building and cooking classes, operating a vessel together builds teamwork. If you share a two-person kayak, then you need to work together to steer properly and move forward at the same time. It takes a bit to get into rhythm, but that’s all part of the fun and experience of your time together. Plus, it’s a great physical activity and provides you with a decent workout.

Kayaking can also be really relaxing, especially if you head out along the Chicago River, Lake Michigan or the Skokie Lagoons. Being outdoors and experiencing nature together can help the two of you bond in a calm setting.

Kayak Chicago offers single or double kayaks starting at $20 per hour. Standup paddle boards are also available for use at Montrose Beach. If you’re both new to kayaking, then Kayak Chicago also provides introductory lessons. Guided tours are available at different times and locations, including a sunset paddle tour for added romance.

5. Try a Craft Brew Pub Crawl

Chicago offers no shortage of unique craft brew pubs and tap houses. If you and your date are into trying different craft beers, then why not make a whole night of it? One of the most popular brew pubs is Revolution Brewing, which is known for its unique craft brews and offering of tasty food as well.

HopLeaf, located in Andersonville, is consistently reviewed as a must-stop beer bar in Chicago. Its selection focuses mainly on Belgian brews, but it’s also known for having a huge and varying draft beer menu.

Over in Wicker Park, Bangers & Lace is a good time for a weekend pub date. It offers a strong selection of craft brews and is known for its offering of sausages, aka bangers.

Lakeview’s DryHop Brewers prides itself on its hop-centric brews. It has a loyal patronage and is regularly busy. DryHop Brewers encourage guests to support its sustainability cause by trying one of its growlers or cans.

These pubs don’t even scratch the surface of what our city has to offer.

6. Visit a Jazz Club

A perfect date idea for old-school romancers is taking part in the best Chicago has to offer in live jazz. Music has evolved in Chicago over time, but the jazz, blues and soul genres have laid their roots here and heavily influenced the city’s current music scene.

Green Mill is a jazz club steeped in history and was one of the known hangouts of legendary gangster Al Capone. This music lounge, though it has been upgraded over the years, maintains its early 20th century feel. Green Mill is open until the early morning hours, but you may want to arrive early as the place tends to fill up.

Another popular destination is Andy’s Jazz Club, which also stays open later. Andy’s has a sophisticated atmosphere that offers of range of music from vintage swing to Afro-pop. Check out one of its Legends of Jazz Lunches for an afternoon of good food and good music.

The Jazz Showcase is a historic jazz venue that’s been a staple in the Chicago music scene since 1947. It has hosted some famous jazz talent over the years. It continues to feature top performers and local musicians every night of the week.

7. Get Silly at a Comedy Club

Though oftentimes improv shows can be hit or miss, at least it’s something the two of you can enjoy – or feel awkward at – together. Chicago is home to several different and premier venues for improv, sketch and standup comedy.

The Second City is a comedy venue that’s been making Chicagoans’ sides hurt since the ‘50s. This place basically invented what we know today as improv and sketch comedy. It’s a fun and relaxing date night event, even just for its history alone.

The iO Theater comedy club has hosted and instructed some very famous comedians over the years, like Amy Poehler, Tina Fey and even the late Chris Farley. You and your date will be guaranteed a fun night with plenty to discuss afterward. With shows almost every night you may even decide to go back for more.

8. Tour an Art Gallery

In a vibrant city like Chicago you have to expect an authentic art scene, and the city doesn’t disappoint. The contemporary art community thrives with galleries, exhibits and events.

Intuit: The Center for Intuitive and Outsider Art is a nonprofit with the cause of bringing awareness to outsider art. The Center features pieces from artists who are entirely self-taught and have never been professionally instructed. It continues its mission to educate by offering regular exhibitions featuring different outsider artists. Experience something new with your date at one of its upcoming events.

For 75 years, the Hyde Park Art Center has been supporting the work of community artists. Check out one of its current or upcoming exhibits to support local contemporary artists. Even if the two of you can’t agree over your taste in art, at least you can agree that supporting the local art scene is something you can feel good about.

If you’re looking for something more mainstream, then the Art Institute of Chicago is a must-see for your art gallery date. Located in Grant Park, the Art Institute of Chicago houses a variety of collections from ancient classical to modern and contemporary art, and even now showcases works of graphic design. Among its more than 300,000 works of art, you and your date will be sure to find at least one or two pieces to discuss.

9. Get Cultured at a Museum

If you’re looking for a rainy-day date idea, then check out one of Chicago’s many museums. The Field Museum is an awesome experience if you and your date are interested in science and the history of life on Earth. Exhibits include dinosaurs, ancient Egypt and an underground adventure, providing you with a full day of learning together.

At the Museum of Science and Industry, the two of you can enjoy getting lost in the mirror maze or descending down into a mock coal mine shaft. This museum offers tons of impressive exhibits and is home to the Omnimax Theater.

For history buffs or anyone who loves this city, the Chicago History Museum is a great place to take your date. Go back in time and discover all the events that made this city what it is today. It did bring the two of you together, after all.

10. Hang Out at Millennium Park

The two of you can appreciate nature at Chicago’s beautifully preserved Millennium Park. As one of the world’s largest green roofs, Millennium Park was impressively built upon the old Illinois Central railyard. Millennium Park is home to hundreds of acres of park space and several different artistic displays and community features.

The McCormick Tribune Plaza & Ice Rink and Park Grill provides a skating facility during the winter and is home to the world’s largest alfresco dining facility during the rest of the year. You can also check out the McDonald’s Cycle Center. This indoor bike station is a cycling enthusiast’s dream and worth visiting if you and your date are into biking.

Hang out in Wrigley Square, take a stroll through Chase Promenade or visit Lurie Garden. There’s tons more to do in Millennium Park. You and your date can hang out in this treasured urban green space all day, touring and visiting the different features without ever spending a dime. No distractions, just simply enjoying your time together and appreciating the city of Chicago.

If you know a couple who can use these 10 date ideas in Chicago, then we ask you to share the love. If it works out for them, then they’ll have you and your awesome date ideas to thank.