22 days in Chicago & New Jersey Itinerary

22 days in Chicago & New Jersey Itinerary

Created using Inspirock United States vacation builder

Make it your trip
Fly
1
Chicago
— 7 nights
Fly
2
Jersey City
— 4 nights
Drive
3
Glenwood
— 2 nights
Drive
4
Columbia
— 2 nights
Drive
5
Point Pleasant Beach
— 5 nights
Drive to John F Kennedy International Airport, Fly to Kuwait City

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Chicago

— 7 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Bring the kids along to The Art Institute of Chicago and Boat Tours & Water Sports. Your cultural itinerary includes sights like The Magnificent Mile and Museum of Science and Industry. Explore Chicago's surroundings by going to Willow Crest Golf Club (in Oak Brook) and Basilica of St. Josaphat (in Milwaukee). And it doesn't end there: get to know the resident critters at Lincoln Park Zoo, steep yourself in history at Frank Lloyd Wright Home and Studio, walk around Millennium Park, and admire the striking features of Marquette Building.

To find where to stay, photos, other places to visit, and other tourist information, use the Chicago tour builder app.

Kuwait City, Kuwait to Chicago is an approximately 18.5-hour flight. Due to the time zone difference, you'll gain 9 hours traveling from Kuwait City to Chicago. In December, Chicago is cooler than Kuwait City - with highs of 3°C and lows of -3°C. Cap off your sightseeing on the 20th (Mon) early enough to catch the flight to Jersey City.

Things to do in Chicago

Historic Sites · Parks · Outdoors · Museums

Side Trips

Jersey City

— 4 nights
Jersey City is the second-most-populous city in the U.S. state of New Jersey, after Newark. You'll visit kid-friendly attractions like Liberty State Park and South Mountain Reservation. Get a sense of the local culture at Wallace House & Old Dutch Parsonage State Historic Sites and Acorn Hall. Venture out of the city with trips to Palisades Interstate Park Commission: State Line Lookout (in Alpine), Trailside Nature & Science Center (in Mountainside) and The Raptor Trust Center (in Millington). There's much more to do: explore and take pictures at Duke Farms, shop like a local with Barsky Gallery, pause for some photo ops at Tear Drop Memorial, and tour the pleasant surroundings at Eagle Rock Reservation.

For traveler tips, ratings, photos, and more tourist information, use the Jersey City trip maker website.

Getting from Chicago to Jersey City by flight takes about 3.5 hours. Other options: drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Expect a bit warmer temperatures when traveling from Chicago in December; daily highs in Jersey City reach 10°C and lows reach 2°C. Finish your sightseeing early on the 24th (Fri) so you can travel to Glenwood.

Things to do in Jersey City

Parks · Wildlife · Outdoors · Nature

Side Trips

Glenwood

— 2 nights
Glenwood is an unincorporated area located within Vernon Township, in Sussex County, New Jersey, United States. Kick off your visit on the 25th (Sat): tee off at Ballyowen Golf Club and then take in the awesome beauty at Ramapo Mountain State Forest. Keep things going the next day: hike along Stairway to Heaven Trail and then stroll through Appalachian Trail - Pochuck Boardwalk.

To see maps, traveler tips, photos, and tourist information, you can read our Glenwood trip builder tool.

Getting from Jersey City to Glenwood by car takes about 1.5 hours. In December, Glenwood is a bit cooler than Jersey City - with highs of 5°C and lows of -3°C. Finish up your sightseeing early on the 26th (Sun) so you can travel to Columbia.

Things to do in Glenwood

Outdoors · Parks · Trails · Wildlife

Side Trips

Columbia

— 2 nights
Columbia is an unincorporated community and census-designated place (CDP) located within Knowlton Township in Warren County, New Jersey, United States, that was created as part of the 2010 United States Census. Kick off your visit on the 27th (Mon): take a peaceful walk through Jenny Jump State Forest and then trek along Columbia Trail. Get ready for a full day of sightseeing on the 28th (Tue): contemplate the waterfront views at Delaware Water Gap and then tour the pleasant surroundings at Lakota Wolf Preserve.

To find traveler tips, reviews, and tourist information, go to the Columbia journey site.

You can drive from Glenwood to Columbia in 1.5 hours. Expect a daytime high around 5°C in December, and nighttime lows around -3°C. Finish your sightseeing early on the 28th (Tue) so you can travel to Point Pleasant Beach.

Things to do in Columbia

Parks · Wildlife · Outdoors · Trails

Side Trips

Point Pleasant Beach

— 5 nights
Point Pleasant Beach is a borough in Ocean County, New Jersey, United States. You'll visit kid-friendly attractions like Edgar Felix Memorial Bikeway and Bliss Price Arboretum and Wildlife Sanctuary. Take a break from the city and head to Edwin B. Forsythe National Wildlife Refuge and Union Transportation Trail. Venture out of the city with trips to Princeton University Chapel (in Princeton), Henry Hudson Trail (in Marlboro) and Lawrence Hopewell Trail (in Pennington). Next up on the itinerary: admire the majestic nature at Rancocas Nature Center and stroll through Cloverdale Farm County Park.

To see ratings, other places to visit, photos, and more tourist information, read our Point Pleasant Beach road trip site.

Traveling by car from Columbia to Point Pleasant Beach takes 2 hours. Traveling from Columbia in December, things will get a bit warmer in Point Pleasant Beach: highs are around 9°C and lows about 0°C. Finish up your sightseeing early on the 2nd (Sun) so you can travel back home.

Things to do in Point Pleasant Beach

Parks · Outdoors · Trails · Wildlife

Side Trips

New Jersey travel guide

3.9
Casinos · Shopping Malls · Beaches
The Garden State
Often overshadowed by its legendary neighbor, New York, New Jersey holds its own as a land of thriving industrial cities, sprawling farmland, and lively coastal towns. Called the Garden State, New Jersey is a hub of entertainment and cultural attractions for the east coast, from the famous sandy beaches and carnival-like atmosphere of the Jersey Shore to alluring Atlantic City, the Las Vegas of the east. New Jersey also boasts a wealth of historical places to visit, including battle sites and memorials, such as George Washington's Revolutionary War headquarters.