You know the feeling. You’re miserable in the moment, but somehow, a week later, you’re telling everyone at brunch about how “incredible” it was. That’s Type 2 fun: the kind that’s terrible while it’s happening and glorious in the retelling. Chicago, a city that regularly serves up 90-degree humidity in July and sub-zero wind chills in January, is basically a factory for it. Here’s where to find it.
1. The Chicago Marathon
Type 1 fun is a leisurely jog along the lake. Type 2 fun is signing up for 26.2 miles through every neighborhood in the city, hitting the wall somewhere around Pilsen, and questioning every decision that led you to this exact spot on Halsted Street. The crowds are electric, the course is famously flat and fast, and by mile 23 your legs have filed a formal complaint. Cross that finish line in Grant Park, though, and you’ll be planning next year’s registration before you’ve even found your gear check bag.
2. The Polar Bear Club Plunge
Every New Year’s Day, hundreds of people run into Lake Michigan. In January. On purpose. The air temperature hovers somewhere between “bracing” and “hostile,” and the water is exactly as cold as you’d expect a Great Lake to be in the dead of winter. The scream you let out upon impact is involuntary. The bragging rights afterward are eternal.
3. Biking the Lakefront Trail in a January Wind
Most people think of the 18-mile Lakefront Trail as a summer activity, and they’re right, that’s when it’s Type 1 fun. Try it in February, though, with a wind whipping off the lake that seems personally offended by your existence, and you’ve got yourself a genuine character-building experience. Your face will go numb somewhere around North Avenue Beach. You’ll still post the photo.
4. A Cubs Day Game in August
Wrigley Field has no roof, minimal shade, and a heat index that turns the bleachers into a convection oven. Add a rain delay, a 14-inning game, and a Cubs team having a rough season, and you’ve got a five-hour ordeal that somehow ends with you already planning next year’s ticket package. Ballpark hot dogs taste better when you’ve earned them through suffering.
5. Riding Out a Chicago Winter Without Leaving
Not an event, exactly, but a season-long trial. Six months of gray skies, black ice on the sidewalks, and a wind chill that makes “polar vortex” a household term. You will complain about it constantly. You will also, come April, feel a strange sense of pride, like you’ve survived something the rest of the country only reads about.
6. Riverwalk Kayaking in a Thunderstorm You Didn’t Check For
Paddling the Chicago River between the skyscrapers is one of the best ways to see the city, until the sky opens up halfway through and you’re paddling for the nearest dock while lightning flickers over the Loop. Soaked, humbled, and slightly concerned about your life choices, you’ll dock the kayak, wring out your socks, and immediately start telling the story to anyone who’ll listen.
7. Standing in Line for a Portillo’s Italian Beef During Lollapalooza Weekend
The line wraps the block. It’s 95 degrees. Someone in front of you is debating sweet versus hot peppers for what feels like an unreasonable amount of time. But that first bite, dipped, dripping down your wrist, standing on a curb in Grant Park with a festival wristband still on? Worth every miserable minute of the wait.
Why we do this to ourselves
There’s something particularly Chicago about all of this: a city built on grit, extreme weather, and an unshakable loyalty to its sports teams and street food. Type 2 fun works because the difficulty is the point. The suffering becomes the story, and the story is better than a day with no friction at all.
So next January, when the wind is doing something unspeakable off the lake, remember: you’re not having a bad time. You’re making a great story for later!
If you are coming to Chicago to earn a story worth telling, The Neighborhood Hotel in Lincoln Park puts you a short walk from the lakefront, Wrigley Field, and the Chicago River. Our Little Italy location puts you close to the best of the West Side near Chicago White Sox park and the United Center. Both properties have full kitchens, which you will appreciate after mile 23 or a polar plunge. Book your stay at The Neighborhood Hotel Lincoln Park or The Neighborhood Hotel Little Italy.
FAQ
Q: What are the best things to do in Chicago in winter?
A: The Polar Bear Plunge on New Year’s Day, biking the Lakefront Trail, and riding out a polar vortex with nowhere to be. Chicago winters are extreme and worth experiencing at least once.
Q: What are fun group activities in Chicago?
A: The Chicago Marathon, Cubs day games at Wrigley, kayaking the Chicago River, and Lollapalooza are all strong options for groups. Each one is more memorable for the suffering involved.
Q: Where should I stay in Lincoln Park Chicago?
A: The Neighborhood Hotel Lincoln Park offers apartment-style suites with full kitchens, a short walk from the lakefront and Wrigley Field.
Q: Is there a boutique hotel in Little Italy Chicago?
A: The Neighborhood Hotel Little Italy is located in the heart of the neighborhood, close to Fulton Market, the West Loop, and UIC.
Q: What is Type 2 fun?
A: Type 2 fun is miserable in the moment and glorious in the retelling. Chicago, with its extreme weather and demanding activities, produces it reliably year-round.
