Day 1 · Wed, May 21
- Stay
Hyatt Regency Chicago
Hyatt Regency Chicago3:00 PM
- Sights
Goose Island Brewery
Goose Island Brewery5:07 PM
- Food
Dinner - Untitled Supper Club (speakeasy)
Untitled Supper Club7:15 PM
Day 2 · Thu, May 22
- Food
Breakfast at the Hotel
Hyatt Regency Chicago8:00 AM
- Sights
Millennium Park, Grant Park & Surrounds
Millennium Park10:00 AM
- Sights
Cloud Gate (The Bean)
Cloud Gate10:24 AM
- Sights
Crown Fountain
Crown Fountain10:48 AM
- Sights
Route 66 Begin sign
Route 66 Begin Sign, Adams St & Michigan Ave11:12 AM
- Sights
Palmer House
Palmer House11:36 AM
- Sights
Chicago Stock Exchange Arch
Chicago Stock Exchange Arch12:00 PM
- Sights
Buckingham Fountain
Buckingham Fountain12:25 PM
- Sights
Willis Tower
Willis Tower12:50 PM
- Food
Lunch - Shaw's Crab House
Shaw's Crab House1:15 PM
- Sights
Magnificent Mile
Magnificent Mile2:00 PM
Day 3 · Fri, May 23
- Tour
River Brunch Boat Tour
Chicago River11:30 AM
- Sights
Navy Pier
Navy Pier3:37 PM
- Food
Dinner - Acanto Restaurant and Wine Bar
Acanto Restaurant and Wine Bar7:45 PM
Day 4 · Sat, May 24
- Food
Brunch at Russian Tea Time
Russian Tea Time11:00 AM
- Sights
The Art Institute of Chicago
The Art Institute of Chicago2:00 PM
- Sights
Chicago Riverwalk
Chicago Riverwalk5:00 PM
- Food
Dinner/Bar - Three Dots and a Dash (Kiki Bar)
Three Dots and a Dash8:00 PM
Day 5 · Sun, May 25
- Event
Belmont Sheffield Music Festival
Wrigleyville11:00 AM
- Food
Dinner - The Purple Pig
The Purple Pig7:30 PM
Day 6 · Mon, May 26
- Flight
Flight Home
1:40 PM
Ideas
- Food
River Roast
River Roast
- Food
Remington's
Remington's
- Food
Yolk (South Loop) Café
Yolk South Loop
- Food
The Gage
The Gage
- Food
Willow Room (Brunch)
Willow Room
- Activity
Scofflaw (Gin Bar)
Scofflaw
- Activity
The Drifter (Speakeasy)
The Drifter
- Activity
Remedy (Happy Hour 4-7PM)
Remedy
- Activity
Delilah's
Delilah's
- Activity
Long Room
Long Room
- Activity
Blind Barber
Blind Barber
- Activity
Village Tap
Village Tap
- Activity
Lone Wolf Chicago
Lone Wolf
- Activity
Haymarket Brewery
Haymarket Brewery
- Activity
The Violet Hour Speakeasy
The Violet Hour
- Activity
Old Crow (Wrigleyville)
Old Crow Smokehouse
- Activity
Bar Sotano (Mexican)
Bar Sotano
- Food
Lou Malnati's (deep dish)
Lou Malnati's
- Food
The Dearborn
The Dearborn
- Food
Pleasant House Pub (Fish & Chips)
Pleasant House Pub