CHI · 5–9

  Chicago, Illinois

Wang Family
Trip to Chicago

September 5–9, 2026 · Five travelers, one city, a lot of deep dish.

Jenny
UA1793 / UA1705
▾
Outbound — Sat 9/5
UA1793, DCA → ORD
6:30 AM → 7:44 AM
Return — Wed 9/9
UA1705, ORD → DCA
7:59 AM → 11:00 AM
Confirmation: GB4H89
Mom & Dad
AA 4150 / AA 3921
▾
Outbound — Sat 9/5
AA 4150, MHT → ORD
7:06 AM → 9:00 AM
Return — Wed 9/9
AA 3921, ORD → MHT
8:25 AM → 11:56 AM
Confirmation: AFMOKT
William & Becky
Driving in
▾
Arrival — Sat 9/5
By car, likely mid-morning (exact time TBD)
Departure — Tue 9/8
By car, morning (exact time TBD)
Pendry Chicago
230 N Michigan Ave
▾
Room 1 — Jenny, Mom, Dad
Queen Queen Guestroom
Check-in Sat 9/5 · Check-out Wed 9/9
Confirmation: 9089487918752
Room 2 — William, Becky
King Guestroom
Check-in Sat 9/5 · Check-out Tue 9/8
Confirmation: 9089487992976
Benefits
Daily breakfast for two per room, $100 F&B credit per room, 12 PM check-in when available, guaranteed 4 PM check-out. AIRE Ancient Baths partner access via concierge.
pendry.com/chicago →

Saturday

Sept 5
7:44 AM

Jenny lands at O'Hare

JENNY
9:00 AM

Mom & Dad land; group takes Uber downtown

JENNY / MOM / DAD
Mid-morning

William & Becky arrive by car

WILLIAM / BECKY
10:00 AM

Breakfast — Wildberry Cafe, Millennium Park

130 E Randolph St
View on map → Website →
ALL 5
Late morning

The Bean (Cloud Gate)

View on map →
ALL 5
Midday

Willis Tower Skydeck; lunch

View on map → Website →
ALL 5
4–9 PM

Chicago Jazz Festival, Millennium Park

View on map →
ALL 5
4:30 PM

Arrive at the First Lady dock

112 E Wacker Dr
View on map → Website →
ALL 5
5:00 PM

Architecture River Cruise aboard First Lady — sunset departure, 90 min


ALL 5
7:00 PM

Dinner — Harry Caray's Italian Steakhouse BOOKED

33 W Kinzie St
Reservation #2110669385
View on map → Website →
ALL 5
After dinner

Comedy show (venue TBD)

Second City → Zanies →
ALL 5

Sunday

Sept 6
6:00 AM

Jenny leaves the Pendry, walks to Streeterville (~15 min)


JENNY
6:30–7:20 AM

Solidcore class, Streeterville

325 E Illinois St
View on map → Website →
JENNY
~7:30 AM

Pastry stop, Paris Baguette


JENNY / WILLIAM
Mid-morning

Dim sum in Chinatown — see Guide for options


ALL 5
1–8 PM

Group splits — Navy Pier & open options

WILLIAM + DAD

WekFest, Navy Pier Festival Hall · 1:00–6:00 PM

JENNY + MOM + BECKY

Options:

  • Great American Lobster Fest, Navy Pier Beer Garden · 1:00–8:00 PM
  • Spa Day
  • Shopping
  • Museum / Sightseeing
View on map → WekFest →
Evening

Korean BBQ dinner — see Guide for options


ALL 5
After dinner

Magic show (placeholder)

Chicago Magic Lounge →
ALL 5

Monday

Sept 7

Indiana Dunes National Park — William & Becky have the car this day.

8–8:30 AM

Leave the hotel by car


ALL 5
9:15–9:30 AM

Arrive West Beach

376 N County Line Rd
View on map → Website →
ALL 5
Day

West Beach; optional Dune Succession Trail (~1 mi, moderate)

Bring: swimsuits, towels, closed-toe shoes for the trail, sunscreen, water, $25 vehicle entrance fee


ALL 5
3–3:30 PM

Leave the park

ALL 5
4:30–5 PM

Back in Chicago

ALL 5
6:00 PM

Dinner — Lou Malnati's BOOKED

439 N Wells St
Reservation #177624
View on map → Website →
ALL 5

Tuesday

Sept 8
Morning

William & Becky depart Chicago

WILLIAM / BECKY
Midday

Lincoln Park Zoo, paired with North Avenue Beach; Lincoln Park Conservatory, on the same grounds

View on map → Website →
JENNY / MOM / DAD
Afternoon

The Art Institute of Chicago; the Chicago Riverwalk; or 360 Chicago Observation Deck

Art Institute → 360 Chicago →
JENNY / MOM / DAD
Evening

Pack for departure

JENNY / MOM / DAD

Wednesday

Sept 9

Departure day.

5:15 AM

Depart hotel by Uber, ahead of Jenny's 7:59 AM flight

JENNY / MOM / DAD
7:59 AM

Jenny's flight departs — UA1705 to DCA

JENNY
8:25 AM

Mom & Dad's flight departs — AA 3921 to MHT

MOM / DAD

Guide

Food & Chicago picks

  Steakhouses

Harry Caray's Italian Steakhouse BOOKED
Sat, 7:00 PM
33 W Kinzie St
Res. #2110669385
Map →Site →
Bavette's Bar & Boeuf
Steakhouse
218 W Kinzie St
Map →Site →
Chicago Cut Steakhouse
Steakhouse, river views
300 N LaSalle Dr
Map →Site →
Gibsons Italia
Steakhouse, Italian menu
233 N Canal St
Map →Site →
Gene & Georgetti
Chicago's oldest steakhouse (1941)
500 N Franklin St
Map →Site →
Steak 48
Steakhouse
615 N Wabash Ave
Map →Site →
Gibsons Bar & Steakhouse
Gold Coast original
1028 N Rush St
Map →Site →
Morton's The Steakhouse
Steakhouse, Wacker Pl
65 E Wacker Pl
Map →Site →

  Dim Sum

MingHin Cuisine
Michelin Bib Gourmand
2168 S Archer Ave
Map →Site →
Triple Crown
Busy, fresh, reservations
2217 S Wentworth Ave
Map →Site →
Imperial
Formerly Cai; lazy Susan tables
2100 S Archer Ave
Map →

  Korean BBQ & Hot Pot

Chubby Cattle
Tableside grilling, AYCE
2162 S Archer Ave
Map →Site →
Daebak
Chinatown, lively
2017 S Wells St, Fl 2
Map →
San Soo Gab San
Lincoln Square, great banchan
5247 N Western Ave
Map →
Wagyu House by The X Pot
Hot pot + BBQ combo, AYCE
1147 S Delano Ct E
Map →Site →

  Deep Dish

Lou Malnati's (Wells St) BOOKED
Mon, 6:00 PM · classic style
439 N Wells St
Res. #177624
Map →Site →
Giordano's
Stuffed style
130 E Randolph St
Map →Site →
Pequod's
Pan style, caramelized crust
405 N Dearborn St
Map →Site →

  Casual, Lunch & Sweets

Portillo's & Barnelli's
Chicago hot dogs, Italian beef
100 W Ontario St
Map →Site →
Al's Beef
Italian beef sandwiches
169 W Ontario St
Map →Site →
The Berghoff
Oldest restaurant in Chicago
17 W Adams St
Map →Site →
3 Arts Club Café at RH
Design gallery courtyard
1300 N Dearborn St
Map →
Time Out Market Chicago
Food hall, 16 vendors
1 S Halsted St
Map →Site →
Doughnut Vault
Small-batch, sells out early
401 N Franklin St
Map →Site →
Margie's Candies
Ice cream & sundaes since 1921
1960 N Western Ave
Map →Site →

  Uniquely Chicago

Chicago Cultural Center
Free — largest Tiffany dome in the world
78 E Washington St
Map →
Garrett Popcorn Shops
The "Chicago Mix," several downtown
Map →Site →
Green Mill Cocktail Lounge
Jazz club since 1907
4802 N Broadway
Map →Site →
Chicago Magic Lounge
1930s-style magic parlor
Andersonville
Map →Site →
Buddy Guy's Legends
Working blues club
700 S Wabash Ave
Map →Site →
Music Box Theatre
1929 movie palace, live organ
3733 N Southport Ave
Map →Site →
Rainbow Cone
Five flavors, one cone, since 1926
9233 S Western Ave
Map →Site →
McDonald's Global Menu
Real international McDonald's menu
1035 W Randolph St
Map →
Chicago Music Exchange
Legendary vintage guitar shop
3316 N Lincoln Ave
Map →Site →
Woolly Mammoth Antiques
Curiosities & oddities shop
1513 W Foster Ave
Map →
Milk Room
One of the smallest bars in the city
12 S Michigan Ave
Map →
The Violet Hour
Unmarked speakeasy cocktail bar
1520 N Damen Ave
Map →Site →

  Hands-On Class Experiences

Chicago Mosaic School
Only nonprofit mosaic school of its kind in North America
1127 W Granville Ave
Map →Site →
Firebird Community Arts
Public glassblowing, no experience needed
Garfield Park
Map →Site →
Ignite Glass Studio
Private glassblowing lessons
West Loop
Map →Site →