16 Fun Anniversary Ideas in Chicago To Celebrate In Style

Those living in Chicago and planning their next anniversary celebration might be trepidatious about coming up with the perfect way to honor the occasion. But the reality is that there are more fun activities than you could possibly imagine to discover in Chicago! No matter the time of year when your anniversary falls, your budget, or any particular preferences you and your partner might have, there are amazing anniversary ideas in Chicago for everyone.

Keep in mind that Peerspace is the internet’s largest marketplace for hourly rentals, and has hundreds of options listed in Chicago alone. Check out some of the many venues in Chicago that are available for your anniversary, and see if they might be a good fit.

Now—just read on for our suggestions of 16 fun anniversary ideas in Chicago that’ll make your next big milestone a truly memorable one.

1. Unwind together at the AIRE Ancient Baths Chicago

At the top of our list of anniversary ideas in Chicago is an activity that prioritizes relaxation above all else. The Chicago location of this luxury chain of baths is located in a restored factory dating back to 1902, which has been preserved to display its exposed brick, wooden beams, and industrial columns. The central conceit of the AIRE Ancient Baths chain is to evoke the experience of the ancient Roman, Greek, and Ottoman baths. And they do an excellent job transporting their visitors to the past!

2. Plan an unforgettable anniversary party at a Peerspace event venue

Now you know that Peerspace is the best platform for finding amazing venues near you. So you might be wondering what kinds of venues we’re talking about.

Check out these examples to get an idea of what Chicago has to offer in terms of venues:

• This minimalist speakeasy in the West Loop, which has tons of glowing five-star reviews and offers space for up to 45 guests at a time.
• This versatile art event gallery on the Lower West Side, known as Vault Gallerie and offering useful amenities like a projector, microphones, and more.
• This boho chic event space at the Logan Square Creative Studio, which is best for more intimate gatherings with as many as 20 people.

If you’re intrigued, conduct a Peerspace search of your own to find Chicago venues exactly tailored to your specifications. Imagine how cool an anniversary event you could plan in some of these spaces!

3. Visit the world-renowned Art Institute of Chicago

This is an especially excellent anniversary idea in Chicago for art lovers, of course, but it’s worth a visit for just about anyone. It’s one of the country’s oldest and largest art museums, so you’ll never run out of galleries to explore, from ancient art to contemporary collections. Just imagine wandering hand in hand through the halls, getting inspired by what you see!

4. Or explore the impressive Adler Planetarium

You may be more excited about science than you are about art—if so, then the Adler Planetarium is going to be a great alternative when it comes to potential museum options for your anniversary! Not only was this the first planetarium in the country, but it’s also packed with fascinating sights. Consider visiting during “Adler at Night,” when the planetarium is open until 9 pm each Wednesday. 

Keep an eye out for all the new spaces in Chicago as they hit the Peerspace platform to have first dibs on the city’s best hidden gems!

5. Go biking along Chicago’s Lakefront Trail

The 18-mile bike trail runs from Ardmore Ave on the north to 71st Street on the south, with continuous views of the western shore of Lake Michigan.Not a big fan of biking? Then you might consider alternatives like rollerblading, walking, or even running (if you and your partner are big athletes). 

6. Listen to authentic live jazz at the Green Mill Cocktail Lounge

The Green Mill cocktail lounge offers a combination of fascinating local history and amazing live performances from jazz musicians. They have live music seven nights a week, and on Tuesdays and Thursday nights, they feature bands that play dance music. So if you and your partner enjoy dancing, be sure to plan your visit on one of those nights.

7. Wander around the Garfield Park Conservatory

Widely known as one of the largest and most impressive botanical conservatories in the country, the Garfield Park Conservatory is often described as “landscape art under glass” simply because it’s such a beautiful destination. Even if your anniversary falls in the dead of winter, it’s worth a visit here because there are eight indoor display gardens, many of which even offer tropical temperatures! If you venture outdoors, you’ll find ten acres of gardens, a water lily pond, and lots more.

8. See a comedy show at the Second City

Comedy fans will adore an evening spent at the Second City, an improv comedy club where you never know what to expect on stage! The Second City has produced hundreds of talented and famous comedians, many of whom you might have heard of (Steve Carell, Stephen Colbert, Amy Poehler, and Tina Fey are just a few). And perhaps you’ll see the next big comedy star at whichever improv show you end up attending!

9. Get a bird’s eye view from the Skydeck Chicago

This suggestion is definitely not for anyone with a serious fear of heights. But if the idea of gazing down at the city through a glass balcony from the 103rd floor of Willis Tower sounds exciting to you and your beloved, then why not incorporate this adrenaline-pumping activity into your anniversary celebration?

10. Play WhirlyBall together

WhirlyBall is a bizarre combination of lacrosse, hockey, basketball, and bumper cars, and if you’re not originally from Chicago, you might not have heard of it till you arrived here. But there’s a reason that Chicago locals have been taking their dates out for WhirlyBall for ages—it’s really fun!

11. Check out the wildlife at Brookfield Zoo

This 235-acre zoological park features a total of 511 species! Spend the day gazing at monkeys, macaws, tigers, and so many more exotic animals. You’ll pretty much never run out of animals to see, so be sure to plan a full day here, if possible. 

Surprise your partner with a gift they’ll never forget after exploring these boudoir photoshoot ideas in Chicago!

12. Relax on one of Chicago’s many beaches

Unlike many other cities, Chicago has 26 miles of scenic lakefront, with more than 24 free beaches that are open to the public each summer. Here’s a full list of all the beaches to help you decide which to visit.

13. See a sports game together

Chicago has baseball, football, basketball, hockey, and soccer teams, so it’s not hard to find opportunities to watch pros play the sports you’re most interested in. Whether you and your partner are fans of the Bulls, Bears, Cubs, White Sox, or another Chicago team, this is a fun way for sports fans to spend an anniversary!

14. Hone your pinball skills and more at Logan Arcade Bar

Do the two of you love playing pinball and old-school video games? Spend your anniversary evening at Logan Arcade Bar for guaranteed entertainment!

15. Go on a “staycation” at a luxury hotel

You may not be traveling for this anniversary, but that doesn’t mean you can’t enjoy the vacation experience of being away from your home and immersed in a relaxing hotel environment. To help you decide, here’s a list of the top hotels in Chicago from Condé Nast Traveler.

16. Put together a stunning anniversary picnic at an outdoor Peerspace venue

If you’re lucky enough to have your anniversary fall during late spring, summer, or early fall, you honestly can’t go wrong with a picnic (unless your partner happens to really hate eating outside in beautiful weather—maybe they’re not a fan of bugs, for example, which is understandable). 

Although you can always have your picnic in one of Chicago’s many beautiful public parks, there’s an alternative that provides quite a bit more privacy and control over the space while you’re in it: renting an outdoor venue in Chicago through Peerspace. Here are some of the best examples of what we’re talking about:

• This central Logan Square secret garden, which is a 900-square-foot, south-facing patio garden divided into sections for dining, sofa seating, flexible open space, and lounging.
• This beautiful outdoor space in Boystown, which feels like an oasis in the midst of the city, tucked away but still near lots of conveniences like restaurants and bars.
• This French manor home and garden, which provides access not only to the stunning gardens but also the historic home itself.

Don’t forget to try searching Peerspace for yourself, too. That way, you can use the platform’s array of intuitive search filters to narrow the results down to meet your exact specifications.

Anniversary ideas in Chicago: conclusion

Now that you’ve gone through this entire list of anniversary ideas in Chicago, we’re willing to bet that at the very least the wheels are beginning to turn in your head as you start thinking of ways to make your partner feel special. And once again, don’t forget that you can always rent a private Peerspace venue in Chicago if you have a particular kind of celebration in mind, whether it’s just the two of you, or you decide to include your closest friends and family in the festivities.

Find unique anniversary venues in Chicago on Peerspace