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Home Alone 2: Christmas Escape from Chicago to New York

schedule8 daysplan for pin_drop4stops directions_car~60 kmon the road flight_landChicago (ORD)fly into

Home Alone 2 is set in New York, but half of it was filmed in Chicago, and this week follows Kevin through both cities at Christmas. You start at the Hilton Chicago, where his Plaza penthouse was really filmed, find Duncan’s Toy Chest in two Chicago buildings and hear a concert in the hall that played Carnegie Hall. On the way to O’Hare you pass the McCallister house in Winnetka, then fly to New York the way Kevin did.

In New York you check in at the Plaza, whose lobby and front are the real thing, cross Gapstow Bridge where Kevin meets the Pigeon Lady, skate at Wollman Rink and end at the Rockefeller Center Christmas tree, where his mother finds him. Mid-December is the time to go: Chicago’s Christkindlmarket and the Walnut Room’s Great Tree are in full swing, and New York is lit up for Christmas.

Day 1–4

Chicago

3 nights · Travel guide
Fly into O’Hare and check in at the Hilton Chicago on South Michigan Avenue: Kevin’s Plaza penthouse was filmed in a suite of this hotel. Evening at the Christkindlmarket on Daley Plaza, Chicago’s German Christmas market.
Duncan’s Toy Chest day: the Rookery on LaSalle Street is the shop from outside, and the Uptown Theatre, a 1925 movie palace up north, was its inside (closed now, so look from the street). Warm up by the Great Tree in Macy’s Walnut Room on State Street.
Symphony Center on Michigan Avenue played Carnegie Hall in the Christmas concert scene: catch a holiday concert there if one is on. Skate at the McCormick Tribune Ice Rink in Millennium Park. The film’s pool scene was shot at the Four Seasons on Delaware Place.
Things to do
Nearby: Hilton Chicago · The Rookery · Uptown Theatre · Symphony Center
Day 4 · on the way

Winnetka

On the way · about 20 min · Travel guide
Drive north to Winnetka and slow down on Lincoln Avenue: number 671 is the McCallister house from both films. It is a private home, so look from the street and keep the drive clear.
Things to do
Nearby: The McCallister house
Day 4 · on the way

O'Hare International Airport

On the way · about 120 min
Return the car at O’Hare, where Kevin follows the wrong man onto the New York plane (the airport also played JFK in the film), and fly to New York in about two hours.
Nearby: O'Hare International Airport
Day 4–8

New York

4 nights · Travel guide
Check in at the Plaza on Fifth Avenue: the lobby and the front are the real hotel from the film. Walk down Fifth Avenue past the Christmas windows.
Central Park: cross Gapstow Bridge over the Pond, where Kevin meets the Pigeon Lady, then skate at Wollman Rink under the skyline. In the evening, a concert at Carnegie Hall, the real one.
Kevin’s sightseeing day: Radio City Music Hall, FAO Schwarz at Rockefeller Plaza (the real toy store behind Duncan’s Toy Chest) and One World Observatory, which stands where the film was shot at the original World Trade Center. The 9/11 Memorial is at its foot.
The finale: the Rockefeller Center Christmas Tree after dark, where Kevin’s mother finds him on Christmas Eve.
Things to do
Nearby: The Plaza · Gapstow Bridge · Wollman Rink · Carnegie Hall
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from ~€1,500 p.p. · a rough estimate for flights and stays; you pick the real ones

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