Public itinerary
Chicago Local Neighborhoods + Course Week
Chicago Local Neighborhoods + Course Week is a 10-day social, diet-aware, first-timer friendly itinerary for Chicago, Milwaukee, planned with TripGuru AI.
Chicago, Milwaukee
Day 1 - Fri, Jun 5
Chicago, Milwaukee
Arrive in Chicago and head to Wicker Park/Bucktown
09:00 AMChicago airport
Drop bags at a Wicker Park or Bucktown hotel
10:30 AMWicker Park / Bucktown
Easy chicken or vegetarian lunch in Wicker Park
12:00 PMWicker Park
Damen Avenue and Milwaukee Avenue boutique wander
01:30 PMWicker Park
The 606 and Wicker Park people-watching break
04:00 PMThe 606 / Wicker Park
Halal-style burger dinner at SALT burgers + fries
06:30 PMSALT burgers + fries, Wicker Park
Day 2 - Sat, Jun 6
Chicago
Logan Square brunch and Blue Line orientation
09:30 AMLogan Square
Plus-size vintage shopping at Luvsick Plus
11:00 AMLuvsick Plus, Logan Square
Chicken or vegetarian lunch around Logan Square
12:30 PMLogan Square
Milwaukee Avenue thrift and boutique crawl
02:00 PMWicker Park / Bucktown
Rest and reset before a social evening
05:00 PMWicker Park / Bucktown hotel area
Social local night: comedy or live music nearby
07:30 PMWicker Park / Logan Square
Day 3 - Sun, Jun 7
Chicago
Move bags to Embassy Suites Downtown Magnificent Mile
09:30 AMEmbassy Suites by Hilton Chicago Downtown Magnificent Mile
Magnificent Mile and 360 CHICAGO orientation
10:30 AMMagnificent Mile / 360 CHICAGO
Diet-aware lunch in River North or Streeterville
12:30 PMRiver North / Streeterville
Chicago Architecture Center river cruise
02:00 PMChicago River
Korean fried chicken dinner at Crisp before Wrigley
05:30 PMCrisp, Lakeview
Cubs vs. Giants at Wrigley Field
07:30 PMWrigley Field
Day 4 - Mon, Jun 8
Chicago
Morning routine at the course hotel
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
Halal chicken or falafel dinner downtown
05:45 PMThe Halal Guys, Wabash
Easy Chicago Riverwalk decompress walk
07:00 PMChicago Riverwalk
Early night at Embassy Suites
08:30 PMStreeterville
Day 5 - Tue, Jun 9
Chicago
Morning routine at the course hotel
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
No-pork dinner near the hotel
05:45 PMStreeterville / River North
Magnificent Mile evening shopping scan
06:45 PMMagnificent Mile
Sunset Riverwalk revisit or early night
08:00 PMChicago Riverwalk
Day 6 - Wed, Jun 10
Chicago
Morning routine at the course hotel
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
Free Grant Park Music Festival concert
06:30 PMJay Pritzker Pavilion, Millennium Park
Late light dinner near Millennium Park or the hotel
08:15 PMLoop / Streeterville
Day 7 - Thu, Jun 11
Chicago
Morning routine at the course hotel
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
Quick chicken or vegetarian bite near Michigan Avenue
05:30 PMLoop / Michigan Avenue
Art Institute late hours visit
06:00 PMArt Institute of Chicago
Evening walk through Millennium Park
08:05 PMMillennium Park
Day 8 - Fri, Jun 12
Chicago
Morning routine at the course hotel
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
Early chicken or vegetarian dinner before the show
05:30 PMRiver North / West Town
Head to The Salt Shed
06:30 PMThe Salt Shed
Lupe Fiasco concert at The Salt Shed
07:00 PMThe Salt Shed
Day 9 - Sat, Jun 13
Chicago
Final course-day morning routine
08:15 AMEmbassy Suites Downtown Magnificent Mile
9–5 final course day
09:00 AMEmbassy Suites Downtown Magnificent Mile
Course-finale dinner near Millennium Park
05:30 PMLoop / Millennium Park
Grant Park Music Festival: Brahms Symphony No. 4
07:30 PMJay Pritzker Pavilion, Millennium Park
Pack and early night before departure
09:30 PMEmbassy Suites Downtown Magnificent Mile
Day 10 - Sun, Jun 14
Chicago
Hotel breakfast and check-out prep
08:30 AMEmbassy Suites Downtown Magnificent Mile
Short final Riverwalk or lakefront stroll
09:30 AMRiverwalk / Streeterville
Collect luggage and head to the airport
10:30 AMEmbassy Suites Downtown Magnificent Mile
Flight departs Chicago
02:00 PMChicago airport