Move over CDFA, Fédération de la Haute Couture et de la Mode, LVMH, or whatever other illuminati type organizations put on the global fashion weeks; the world major marathons are now the cultural movers of culture, culturally. These weekends remain laser focused on the intense beauty of marathon racers, but the ascension of running in the ranks of the global zeitgeist has created a festival style event that can move an economy.
So what does Chicago have to offer this upcoming weekend? Running or not, your answer awaits below in a guide to a guaranteed good time.
(I would like a raise for my contributions to B-Mail copywriting). Sincerely, John.
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1. The Bandit Pop Up in the Tribune Tower
If you're reading this its too late. Not even a Drake joke, but it's likely too late for me to break any news regarding our pop up to you. We'll be at the Tribune Tower (435 N Michigan Ave) all weekend and our teams have been working quite literally around the clock thinking about the best way... to blow you away. It's a windy city. Bundle up. The Chicago Simulation Research Center awaits. See you soon.
2. Where to Cheer at the Chicago Marathon
Ok, so obviously if you're racing: congrats, you can do incredibly hard things and we're infinitely proud of you. If you have the great pleasure of supporting or watching the race, this is a real treat. I consulted a brain trust chat I have with Steve Finley, Luke McCambley, and Tim Rossi. They know a thing or two because they've seen a thing or two (aka a wild number of marathons). Read below...
TLDR: Stay by the bridges. Enjoy the vibes.
3. There's a couple good shows...
Honestly, a pretty solid weekend of music in Chicago. Mainly for the non-racers but alas, we all need to have some sort of weekend while we are here. The iconic Metro/Smartbar weekender in Chicago is a go. Stereolab on Friday night, and Nico Segal and The Social Experiment on Saturday. Chance The Rapper just dropped an album. Sunday Candy, I love my wife!
Late night house downstairs at Smartlab if you're into that sort of thing. Tix tix tix.
4. Bulls vs. Cleveland Cavs Preseason Game (Thursday)
Low key, we did this last year and it was a great time. It's preseason, so tickets are as cheap as they'll ever be and the basketball is as basketball as it'll ever be. If you get close enough to the court, you can see the ghost of Lebron's past at Cleveland.
5. Go see One Battle After Another at the Music Box
RACER FRIENDLY!! Grab a late lunch, early dinner, or mid day matinee to get off your feet. The Chicago Music Box Theater is showing film festival series, horror classics, and some current goodies. I have been publicly and privately shamed by the creative team for not seeing One Battle After Another yet, so I will do them one better -- see it at The Chicago Music Box Theater on Chicago Marathon Weekend in 70mm (because my level of mystic, sophistication, and culture reigns supreme - and yours should to). See you there.
6. Playoff Baseball at Wrigley Field
Chicagoans take playoff baseball at Wrigley Field when they can get it, and they don't get it often. (Come for me.) But they have it, and the energy will be something (win or lose, but probably lose). They are down 2-0 in a best of 5 series to their arch nemesis, the Milwaukee Brewers, but the series is back in in Wrigleyville...
- Game 3 Wednesday 4:08 CST
- Game 4 Thursday 6:08 CST
- Game 5 Saturday 7:08 CST
7. Chicago Marathon 3Run2 Afterparty
I went the previous 2 years and its actually a good time. Some of these post race afterparty events can be a drag, but the Chicago crowd knows how to party. Check it out.
9. Go take a stroll down down in Bucktown
Helluva neighborhood with some great shopping and dining. There's also a gorgeous running path in case you're into that sort of thing.
10. The stores you know, and the stores you dont.
- Half Evil (Wicker Park) — Starting this off with a true, down to the bone, its in their DNA streetwear brand. It's refreshing to see an offspring of Pharrell & Nigo's Billionaire Boys Club, Bobby Hundred's The Hundreds, James Jebbia's Supreme in our current streetwear world of gorp core galore. We're watching a true streetwear giant in their teenage years. Sam Half Evil is super dope and doing things the way they should be done.
- Uprise Skateshop (Wicker Park) — the city’s skate institution; shoes, decks, culture. 1820 N Milwaukee.
- Notre (West Loop) — museum-level curation of sneakers and designer apparel. 118 N Peoria. Our guy Grant is their photographer, and also will be ours for the weekend!
- Moth (Bucktown) — Women's Nordic/Japanese minimalism, clothes + home. 2008 N Damen. Nordic/Japanese clothing combo is worth the stop alone.
- Kith (Chicago) — They were raised in the streetwear game, they cut their teeth with some legendary Asics collaborations, and now they've graduated to stand alongside blue chip luxury brands like they belong. Love them or hate them, you still watched. They just opened a beautiful new flagship alongside a 6 (SIX!!) shoe collab with Asics. Check it out.
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Vintage Round Up —
- Kokorokoko (Wicker Park) — ’80s/’90s pop vintage w/ attitude. 1323 N Milwaukee.,
- Knee Deep Vintage (Pilsen) — 40s–90s, wearable and priced right. 1219 W 18th.
- Very Best Vintage (Pilsen) — tight, curated rack for real wardrobes. 1346 W 18th.
- Lost Girls Vintage (Logan Square & West Town) — two shops, strong edits, zero dust.
8. Dine at an Institutional Chicago Restaurant
This list is a combination of my past experiences, the latest and greatest on Beli, and some recs from our AI overlords. ChatGPT even gave me a blurb on what you should say to the waiter when you order (??). Take it or leave it.
- Girl & the Goat (Fulton Market) — Goat-famous for a reason. Pig face, big grin. Say: “Wood-oven pig face and whatever veg is roasted tonight.”
- The Berghoff (Loop) — Beer hall since 1898. Order sauerbraten, toast history. Say: “Sauerbraten, spätzle, and a pint of whatever’s freshest.”
- Manny’s Deli (Near West) — Power lunch, plastic tray. Corned beef + latke, no small talk. Say: “Corned beef, sliced thick, latke on the side—half sour pickles.”
- Gene & Georgetti (River North) — Old-school steak, zero TikTok. Bone-in ribeye, jacket optional. Say: “Bone-in ribeye, medium-rare, hash browns well-done.”
- Gibsons (Gold Coast) — Martini with a mortgage. Prime Angus, paparazzi not included. Say: “Gibsons martini, blue-cheese olives; 22-oz W.R.’s Cut.”
- Au Cheval (West Loop) — The burger your burger follows. Double w/ bacon + egg. Say: “Double cheeseburger, add bacon and egg—fries on the side.”
- Frontera Grill (River North) — Bayless doing Bayless. Mole for the soul. Say: “Chicken in mole negro, start with guac and a Paloma.”
- Lou Mitchell’s (Loop) — Route 66 breakfast theater. Pancakes, donut hole starter. Say: “Short stack with bacon; coffee top-ups, please.”
- Pequod’s (Lincoln Park) — Caramelized pan pie, cult-only. Sausage + giardiniera. Say: “Pan sausage with giardiniera—light sauce, extra crisp edge.”
- Lou Malnati’s (Various) — Deep-dish diplomacy. The “Lou,” settle debates later. Say: “The Lou, butter crust—house salad to start.”
- Giordano’s (Various) — Stuffed and unapologetic. Pepperoni, patience. Say: “Medium stuffed pepperoni; we know it’s a wait.”
- Portillo’s (Various) — Beef, dogs, cake shake chaos. Italian beef, dipped, hot. Say: “Italian beef, dipped, hot peppers—and a chocolate cake shake.”
- Al’s #1 Italian Beef (Little Italy) — The origin story. Beef, dipped, sweet + hot. Say: “Beef, juicy, sweet and hot—add small fries.”
- Mr. Beef (River North) — No frills, all drips. Beef + spicy giardiniera. Say: “Beef hot—extra giardiniera. Keep it messy.”
- Johnnie’s Beef (Elmwood Park) — Suburban pilgrimage. Beef hot, lemon ice chaser. Say: “Beef, juicy, hot peppers—and a lemon ice to-go.”
- Jim’s Original (UIC/Maxwell) — Maxwell Street Polish, 2 a.m. poetry. Onions + sport peppers. Say: “One Maxwell Polish—grilled onions and sport peppers.”
- Superdawg (Gladstone Park) — Carhop time capsule. Superdawg, crinkles, neon nostalgia. Say: “Superdawg with everything—add crinkle fries.”
- Wiener’s Circle (Lincoln Park) — Char-dog, char-attitude. Ketchup is a trap. Say: “Char-dog, everything—no ketchup. Cheese fries, too.”
- Original Rainbow Cone (Beverly + stands) — Five flavors, one flex. Get the slice. Say: “One Rainbow Cone slice—classic stack.”
- Twin Anchors (Old Town) — Ribs with Rat Pack lore. Baby-backs, Zesty sauce. Say: “Baby-back ribs, Zesty sauce—side of slaw.”
- Harold’s Chicken (South Side) — Fried-chicken scripture. Say: “Half dark, mild sauce on the chicken and fries—salt and pepper.”
- Lem’s Bar-B-Q — Rib-tip institution, smoke signals visible from space. Say: “Rib tips, hot sauce on the side—end pieces if you got ’em.”