Chicago — Summer 2026

The plan

Thu

Jul 16

JAX Rubins land — downtown hotel night

Arrival Our family only

Our family flies in a night early and stays downtown before the reunion crowd arrives. Land late, check in, and keep it easy — the river and the Loop are right outside the door.

Evening · arrive Thu

Fly Jacksonville → Chicago Midway (MDW)

JAX Rubins land at Midway ~8:45 PM. The rest of the family arrives tomorrow (Friday).

Check in

Hotel Chicago Downtown, Autograph Collection

Our one hotel night, in the landmark Marina City "corncob" towers on the river at 333 N. Dearborn (check-in 4 PM). We move to the shared Airbnb tomorrow.

Hotel info

Nightcap

Riverwalk stroll

If anyone's still up, the Chicago Riverwalk is steps away — a quick lit-up-skyline walk to shake off the flight before bed.

Fri

Jul 17

Everyone arrives — move to the Airbnb

Reunion begins Dinner booked

The Charlotte, Denver, and Miami Rubins fly in through the afternoon. We check out of the downtown hotel and into the shared Airbnb, the Miami Rubins head to the Four Seasons, and everyone converges for the first big dinner.

Through the day

The rest of the family flies in

Charlotte → Midway ~12:35 PM · Miami → O'Hare ~3:00 PM · Denver → O'Hare ~4:30 PM. Two airports — see the Getting There table for the full grid.

Afternoon

Check in — Airbnb (Four Seasons for Miami)

The JAX, Charlotte, and Denver Rubins settle into the shared Airbnb — our base Friday through Tuesday — while the Miami Rubins check in at the Four Seasons on the Mag Mile. Drop bags, claim rooms, and regroup before dinner.

Airbnb listing Four Seasons

7:15 PM · reserved

Dinner — Club Lucky

An old-school Bucktown supper club (1824 W. Wabansia) — red sauce, martinis, and room for a big table. Reservation's set for 7:15.

Club Lucky

Sat

Jul 18

Cubs at Wrigley

Tickets booked The one fixed plan

The anchor of the whole trip. Get up to Wrigleyville with time to wander before first pitch, watch the Cubs, and keep the evening low-key with pizza back at the Airbnb.

Late morning

Explore Wrigleyville

Get to the neighborhood early — the marquee, Gallagher Way, and the bars and shops around the ballpark are half the fun before the gates open.

Lunch

Eat at Wrigley

Plan on ballpark food for lunch — grab it in and around the stadium.

~1 PM first pitch

Chicago Cubs game · Wrigley Field

Afternoon game at one of baseball's great old ballparks (1060 W. Addison). Tickets are booked. ✅

Wrigley Field

For first-timers

Grab a First-Timer Certificate

First Cubs game? Stop by a Fan Services booth — third-base side, or near the bleachers — to pick up a free personalized certificate. A fun keepsake for the kids.

Evening

Pizza at the Airbnb

Casual family night in after the game — pizza back at the house, no reservation to make.

Sun

Jul 19

Downtown — the Bean, the river, the lake

Sightseeing Dinner booked

The classic downtown day. Hit Millennium Park, walk the river, and — if we book it — take the architecture cruise, then head north for dinner in Uptown.

Morning

Millennium Park — Cloud Gate & Crown Fountain

"The Bean" for the photo, then let the kids splash at Crown Fountain on a hot day. Free, central, and steps from the Riverwalk. Bring a towel and a change of clothes.

Millennium Park

Chicago Riverwalk

Flat, easy walk along the river between the bridges — cafés, skyline, and a natural spot to catch the architecture cruise.

If we book it

Architecture River Cruise

The 90-minute Chicago Architecture Center docent cruise aboard Chicago's First Lady — the city's do-once. Pricing is dynamic; book a daytime slot in advance. Free activity kits for kids at the box office.

CAC River Cruise

6:30 PM · reserved

Dinner — Sun Wah BBQ

Hong Kong–style Chinese BBQ in Uptown (5039 N. Broadway) — a James Beard "America's Classic," famous for the Beijing Duck Dinner. Reservation's set for 6:30.

Sun Wah BBQ

Cloud Gate, 'The Bean,' in Millennium Park

The Chicago River winding through downtown skyscrapers

Mon

Jul 20

Museum of Science & Industry

Pre-book tours Dinner booked

A big hands-on museum morning in Hyde Park — the submarine and the coal mine are the big draws, but their timed tickets sell out, so lock them in first. Dinner back near downtown in the Gold Coast.

~10 AM

Museum of Science & Industry

The largest science museum in the Western Hemisphere (5700 S. DuSable Lake Shore Dr), ~20–30 min south of downtown. General admission $25.95 adult / $14.95 child (3–11). Half a day covers the highlights.

MSI official All exhibits

Timed ticket · sells out

U-505 Submarine on-board tour

Walk inside the only German U-boat in the U.S. (+$18 adult / +$14 child, ~25 min). The exhibit hall is free with admission — only the on-board walk-through is the paid, timed add-on.

U-505 tour

Timed ticket · sells out

Coal Mine tour

Train-car ride into a simulated working mine (+$12 adult / +$9 child, ~25 min). Dark, loud, and a moving car. Book both timed tours online before the day.

Coal Mine tour

6:30 PM · reserved

Dinner — Hugo's Frog Bar & Fish House

Gold Coast seafood-and-steak classic next to Gibsons (1024 N. Rush St). Reservation's set for 6:30.

Hugo's Frog Bar

The Museum of Science and Industry building in Hyde Park

Tue

Jul 21

Departures

Travel day

Everyone scatters back home on staggered flights out of both airports. Check out of the Airbnb and mind who's leaving from Midway vs. O'Hare.

Staggered · all day

Fly home

Denver → O'Hare 12:00 PM · Jacksonville → Midway 12:50 PM · Miami → O'Hare 2:30 PM · Charlotte → Midway 6:15 PM. Full grid in Getting There.

Open options

Possible Activities

Not pinned to any day — grab any of these if a morning opens up, the weather turns, or a subset of the family wants to split off. Hours and prices are best-guess; confirm before you go.

The Field Museum

Museum CampusDaily 9 AM–5 PMfrom ~$30 adult

Great natural-history museum on the lakefront — SUE the T. rex, the 122-ft Máximo, a walk-through Egyptian tomb. Closer to downtown than MSI and fully indoor, so a solid hot- or rainy-day pick. Pairs with Shedd Aquarium next door.

Official site Tickets

360 Chicago

Mag MileDaily 9 AM–11 PM~$30 adult

94th-floor observation deck atop the old John Hancock Center, with the TILT platform that leans you out over Michigan Ave (42" height minimum). Often shorter lines than Willis Tower, and open late — a great clear-evening sunset stop.

Official site Hours & pricing

Lakefront Trail

Lake MichiganFree · open dailyDivvy bikes

An 18.5-mi paved path along the lake with mostly separated bike and pedestrian lanes. Rent Divvy bikes (~$18 day pass) and ride the flat, scenic Museum Campus → Navy Pier segment (~2–3 mi). Little shade — pack sunscreen and water.

Divvy bikeshare Trail overview

More if you want it: Navy Pier · Shedd Aquarium · Willis Tower Skydeck · Art Institute of Chicago

Where we're eating

Eat & Drink

Three dinners are on the books. The rest are family favorites and good-for-a-crowd backups — pick from these for lunches and the open nights.

Booked 3 dinners

Club Lucky

BucktownItalian supper clubFri · 7:15 PM

Old-school neighborhood spot near Lincoln Park — red sauce, martinis, and room for the whole table. Top of the list. Outdoor patio.

Website

Sun Wah BBQ

UptownHong Kong BBQSun · 6:30 PM

James Beard "America's Classic," known for the Beijing Duck Dinner and whole roast pig. A Chicago institution since 1986.

Website

Hugo's Frog Bar & Fish House

Gold CoastSeafood & steakMon · 6:30 PM

Oysters, frog legs, and Gibsons prime steaks, right next to its famous steakhouse sibling on Rush St.

Website

Options & backups not booked

Wildberry Cafe

Prudential PlazaBreakfast & brunch

"Best brunch for kids" per Uncle Bruce — huge menu, right downtown near Millennium Park. Good pre-sightseeing fuel-up.

Website

Topo Gigio

Old TownItalianPatio

A longtime favorite on a cool retail strip near Lincoln Park, with an outdoor patio. Great neighborhood pick.

Website

Quartino

River NorthItalian small plates

Big, lively downtown spot built for a crowd — shared plates and good table wine. Easy for a large group.

Website

Rosebud on Rush

Gold CoastItalianClassic

An old-school, more-downtown Chicago classic — Rush St. institution with a proper white-tablecloth feel.

Website

Logistics

Getting There & Lodging

Four families, two airports. Midway (MDW) is closer to the North Side and the Airbnb; O'Hare (ORD) is the bigger hub to the northwest. Times below are the current plan — double-check your own itinerary.

Family	From	Airport	Arrive Chicago	Depart Chicago
Jacksonville	JAX	MDW	Thu · 8:45 PM	Tue · 12:50 PM
Charlotte	CLT	MDW	Fri · 12:35 PM	Tue · 6:15 PM
Denver	DEN	ORD	Fri · 4:30 PM	Tue · 12:00 PM
Miami	MIA	ORD	Fri · 3:00 PM	Tue · 2:30 PM

Hotel Chicago Downtown, Autograph Collection

Marina City · River NorthThu 7/16 → Fri 7/17JAX family only

Our one early-arrival night, in Bertrand Goldberg's landmark "corncob" towers on the river at 333 N. Dearborn (entrance on N. State St). Check-in 4 PM, checkout by 12 PM.

Hotel info

Shared Airbnb

Reunion baseFri 7/17 → Tue 7/21JAX · CLT · Denver

The home base for the reunion, Friday through Tuesday — the Jacksonville, Charlotte, and Denver Rubins. Have a look at the place:

Airbnb listing

Four Seasons Hotel Chicago

Mag Mile · Gold CoastReunion nightsMiami Rubins

The Miami Rubins' stay — luxury tower at 120 E. Delaware Pl (in the 900 N. Michigan building), with lake and skyline views right off the Magnificent Mile.

Hotel info

Good to know: mid-July in Chicago is hot and humid — plan for heat, water, and the Crown Fountain / lakefront cool-offs. Getting around downtown is easiest by rideshare, CTA, or Divvy bikes; parking a car downtown is pricey.