Chicago, Illinois
September 5–9, 2026 · Five travelers, one city, a lot of deep dish.
Jenny lands at O'Hare
JENNYMom & Dad land; group takes Uber downtown
JENNY / MOM / DAD| Uber | ~$35-70, ~25-35 min, door to door |
| Blue Line | $5 one-way (O'Hare surcharge) · O'Hare is the line's terminus, so you board an empty train · ~40-45 min to Washington station · ~0.6 mi / 12-13 min walk east to the Pendry |
Breakfast — Wildberry Cafe, Millennium Park
130 E Randolph St JENNY / MOM / DADWilliam & Becky arrive by car
WILLIAM / BECKYLate lunch
Dinner — Harry Caray's Italian Steakhouse BOOKED
33 W Kinzie St| First Lady (CAC) | Wendella | Shoreline | Mercury | |
| Duration | 90 min | 90 min | 75 min | 90 min |
| Route | All 3 branches | All 3 branches | Main + part of south branch | River + Lake Michigan via the lock |
| Buildings | ~50 | ~50 | ~30 | Fewer river, more open-lake views |
| Price | ~$54-62 | ~$52-58 | ~$40-45 | ~$40-50 |
| Notes | CAC-trained docent | Heated indoor cabin | Departs most frequently | Includes Lake Michigan via the lock |
| Walk from Pendry | ~0.3 mi, ~6 min | ~0.4 mi, ~8 min | ~0.4 mi, ~8 min | ~0.3 mi, ~6 min |
"3 branches" refers to the Chicago River's Main, North, and South branches, which split downtown into a Y-shape. A cruise covering all three (First Lady, Wendella) sees more river and more buildings than one that stays mostly on the Main Branch (Shoreline).
Jenny leaves the Pendry, walks to Streeterville (~15 min)
Pastry stop, Paris Baguette
Dim sum in Chinatown — see Guide for options
Group splits — Navy Pier & open options
WILLIAM + DAD
WekFest, Navy Pier Festival Hall · 1:00–6:00 PM
JENNY + MOM + BECKY
Options:
Korean BBQ dinner — see Guide for options
Indiana Dunes National Park — William & Becky have the car this day.
Leave the hotel by car
West Beach; optional Dune Succession Trail (~1 mi, moderate)
Bring: swimsuits, towels, closed-toe shoes for the trail, sunscreen, water, $25 vehicle entrance fee
Leave the park
ALL 5Back in Chicago
ALL 5William & Becky depart Chicago
WILLIAM / BECKYLincoln Park Zoo, paired with North Avenue Beach; Lincoln Park Conservatory, on the same grounds
JENNY / MOM / DADThe Art Institute of Chicago; the Chicago Riverwalk; or 360 Chicago Observation Deck
JENNY / MOM / DADPack for departure
JENNY / MOM / DADDeparture day.
Depart hotel by Uber, ahead of Jenny's 7:59 AM flight
JENNY / MOM / DADJenny's flight departs — UA1705 to DCA
JENNYMom & Dad's flight departs — AA 3921 to MHT
MOM / DADChinatown also has several small reflexology spots (~$44/session) within a block or two of the Cermak-Chinatown Red Line stop — easy to combine with the Sunday dim sum plan.