Chicago • Sept 4–7, 2026
Wes's
Bachelor Party
Four days in Chicago. Golf and a boat charter, White Sox and Second City.
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Days
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Hrs
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Min
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until Friday check-in.
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01
THE CREW
Wes
Lucas
Omar
Mike
Keegan
Neil
Justin
02
HOME BASE
Wicker Park, Sept 4–7 (3 nights).
Airbnb is booked. Walkable to dinner and bar options, and about two blocks from the Damen Blue Line — a direct train to O'Hare one way and the Loop the other.
03
Itinerary
Subject to change
Friday
Sept 4 · Arrival + Dinner
AFTERNOON
Arrive, check in, stock the house
Blue Line from O'Hare to Damen, about 35 minutes. Grocery run for breakfast, snacks, and drinks for the house.
7:30 PM · DINNER
Nice dinner in Wicker Park / Bucktown
Not booked yet.
AFTER DARK
Bars near the house
TBD in Wicker Park
Saturday
Sept 5 · Golf + Boat Day
9:00 AM · GOLF
Sydney Marovitz — 9 holes
Public lakefront course, roughly $35–45 per person. Chicago Park District releases tee times about 7 days ahead, so both need to be grabbed the morning they open.
3:30 PM · BOAT
Boat charter — Chicago Boat Company
Two hours, BYOB.
EVENING
Dinner downtown
The boat docks downtown, so stay there. Lou Malnati's in River North for deep dish (expect a 45+ minute wait, order a pie ahead) or Mr. Beef for Italian beef. Bars on Hubbard St after; Three Dots and a Dash is the one worth a line.
Sunday
Sept 6 · Ballgame + Second City
~11:00 AM · Pregame
Cork and Kerry at the Park
Irish bar near the field. 3259 S Princeton Ave, Chicago, IL 60616
1:10 PM · FIRST PITCH
White Sox vs. Twins
Tickets run about $20–40 and rarely sell out, so this can be booked late. Red Line to Sox–35th if we don't drive.
7:00 PM · COMEDY
Second City Mainstage
Old Town, about $70-115.
~9:00 PM · DINNER
Dinner in Old Town
TBD
Monday
Sept 7 · Recovery + Departure
~11:00 AM BRUNCH
Brunch near the house
TBD in Wicker Park
THEN
Check out
Blue Line back to O'Hare from Damen, about 35 minutes.