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Opening the trip…
Adventurers
3 adventurers
Push to calendars
Sync this day or the whole trip to each adventurer — ICS download, Add to Google Calendar, or email the links. Live Google write is not wired (needs per-person OAuth).
Sat Sep 26
Adventures of the Day
3 of 3
Downtime
Annie's place · Wicker Park
6:30–8:30 PM
3 of 3
3 of 3
Full adventure · 5 pins
5 pins · Route follows list order 1→2→3→4→5
1→2 0.2 km · 4m walk
2→3 3.2 km · 14m drive
3→4 0.1 km · 4m walk
4→5 0.2 km · 4m walk
Friend Pitch
Friend notes, reels, and ASK RUD add-stop proposals land here — not on the day list. A multi-place reel unpacks into one card per item (location + Preview back to the reel). Sequence the board, drop what you do not want, then Apply to day is the only write onto Plan and Execute.
Pasted
Art of Pizza
Live desk save for beta share.
Google Maps
Open MapsArt of Pizza Chicago
Friend pitches
Deep dish as a personality. Lou's, you have to.
Deep dish as a personality. Lou's, you have to.
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Open MapsDeep dish as a personality. Lou's, you have to. Chicago
Pizza
Pequod's
Deep dish with a caramelized crust. Worth the wait if Saturday still has air.
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Open MapsPequod's Chicago
Pizza
Art of Pizza
Stuffed, not a personality. If the table is hungry after the river.
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Open MapsArt of Pizza Chicago
Pizza
Bartoli's
Thin-crust tavern pie. Neighborhood, not a pilgrimage.
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Open MapsBartoli's Chicago
Pizza
Giordano's
Stuffed, tourist-proof. Only if someone in the party insists.
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Open MapsGiordano's Chicago
Italian beef
Al's Beef
Italian beef, dipped. Stand up. Do not turn it into a sit-down.
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Open MapsAl's Beef Chicago
Italian beef
Mr. Beef
The other beef. Same rules — sandwich, then walk.
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Open MapsMr. Beef Chicago
Hot dogs
Clark Street Dog
Char dog, sport peppers. Late, standing.
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Open MapsClark Street Dog Chicago
Hot dogs
The Wieners Circle
Chaos with a char dog. Only if the night still has teeth.
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Open MapsThe Wieners Circle Chicago
Hot dogs
Devil Dawgs
Another dog if Clark Street is a hike.
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Open MapsDevil Dawgs Chicago
Honorable
Billy Goat Tavern
Cheezborger. Down the stairs. Not dinner.
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Open MapsBilly Goat Tavern Chicago
Honorable
Margie's Candies
Hot fudge, booths, no agenda. If the evening fails beautifully.
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Open MapsMargie's Candies Chicago
Note
Chicken Vesuvio
The dish, not a reservation. Order it if a room has it. Do not hunt a Vesuvio restaurant.
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Open MapsChicken Vesuvio Chicago
ASK RUD
Chicken Wing Tasting
Bucketlisters chicken wing tasting event in Chicago on 2026-09-26, evening slot after downtime.
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Open MapsChicken Wing Tasting Chicago
Pasted
Chop Shop Wicker Park Buffs Bar
Chop Shop Wicker Park Buffs Bar
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Open MapsChop Shop Wicker Park Buffs Bar Chicago
Note
Hot-dog serendipity
If a stand appears, get the dog. Do not itinerary it.
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Open MapsHot-dog serendipity Chicago
ASK RUD
Big Star
Loud Wicker Park tacos and margaritas on Friday night after the roof drink.
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Open MapsBig Star Chicago
ASK RUD
River Kayak Tour
Sunday morning river kayak on the Chicago River, 8–10am window.
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Open MapsRiver Kayak Tour Chicago
ASK RUD
The Bean
Quick hit at Millennium Park during the Sunday recovery walk before heading to the airport.
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Open MapsThe Bean Chicago
ASK RUD
Itoko
8pm Friday dinner reservation at Itoko after the roof drink.
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Open MapsItoko Chicago
ASK RUD
Big Star
Loud Wicker Park tacos and margaritas at 8pm Friday after the roof drink.
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Open MapsBig Star Chicago
ASK RUD
Chicago River Architecture Cruise
90-minute boat tour hitting the main river loops and skyline views, depart from Michigan Ave dock around 15:00 after recovery.
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Open MapsChicago River Architecture Cruise