5-Day NYC and Chicago at Christmas Itinerary

Arrive in New York

Fly into JFK, LaGuardia or Newark and take a train, bus or taxi to a Midtown hotel, then drop your bags.

Midtown lunch and a pizza slice

Grab a classic New York slice or a hot pastrami sandwich to fuel up for the afternoon.

Bryant Park Winter Village

Browse the glass kiosks for gifts and treats and watch skaters on the rink behind the New York Public Library.

Rockefeller Center tree and the Saks light show

See the giant tree glowing above the Rink, then cross Fifth Avenue for the Saks Fifth Avenue holiday light show.

Fifth Avenue holiday windows

Walk Fifth Avenue from about 59th Street south, viewing the elaborate windows at Bergdorf Goodman, Saks and other flagships.

Skate at Bryant Park

Book a time slot and skate on the free-admission rink, bringing your own skates or renting them.

Top of the Rock

Head up Top of the Rock for skyline views from right above the Christmas tree, booking a sunset slot if you can.

Radio City Christmas Spectacular

See the Rockettes in the Christmas Spectacular at Radio City Music Hall, or another holiday show on Broadway.

Macy's Herald Square

Admire the holiday windows at Macy's flagship and visit Santaland if you're traveling with kids.

DUMBO and the Brooklyn waterfront

Ride the subway to DUMBO for cobblestone streets, cafes and Manhattan skyline views from Brooklyn Bridge Park.

Holiday market browsing

Return to Manhattan to browse the Union Square Holiday Market's gift stalls, or rest up at your hotel before a cold night.

Dyker Heights Christmas lights

Take the subway or a tour bus to Dyker Heights and walk the blocks of over-the-top light displays.

Fly to Chicago

Fly from LaGuardia or JFK to O'Hare or Midway (about 2-2.5 hours), set your watch back an hour and take the L downtown.

Check in to a Loop or River North hotel

Drop your bags at a hotel within walking distance of State Street and Michigan Avenue.

Christkindlmarket in Daley Plaza

Wander the wooden huts for ornaments and bratwurst, and sip hot Gluhwein from a boot-shaped souvenir mug.

Magnificent Mile lights

Walk north from the river along Michigan Avenue beneath trees strung with more than a million lights.

Breakfast and the Bean

Have a warming breakfast, then walk to Millennium Park to see Cloud Gate dusted with frost.

McCormick Tribune Ice Rink

Skate in Millennium Park with the skyline above you; admission is free, skate rental is extra and reservations may be required.

Macy's Walnut Room and State Street

See the Great Tree in Macy's Walnut Room on State Street and the holiday windows outside.

Lincoln Park ZooLights

Take a bus north to Lincoln Park Zoo for millions of lights, animal sculptures and hot chocolate.