34 days in Chicago & New York City Itinerary

34 days in Chicago & New York City Itinerary

Created using Inspirock United States tour itinerary builder

This plan was created by another user.  Make it your plan

Route & dates

34 days in Chicago & New York City Itinerary

Start: Singapore
Fly:  23​h 15​min
1
Chicago
— 15 nights
Fly + bus:  4​h 45​min
2
New York City
— 15 nights
bus + Fly:  21​h 30​min
End: Singapore

15
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your inner history buff will appreciate Millennium Park and Holy Trinity Orthodox Cathedral. Head to The Magnificent Mile and Chicago Cultural Centerfor some retail therapy. Change things up with these side-trips from Chicago: Chesterton (Coffee Creek Watershed Preserve & Cowles Bog), Edward L. Ryerson Conservation Area (in Riverwoods) and Independence Grove Forest Preserve (in Libertyville). The adventure continues: admire nature's wide array of creatures at Lincoln Park Zoo, see what you can catch with a fishing tour, explore the world behind art at The Art Institute of Chicago, and identify plant and animal life at Red Oak Nature Center.

To find traveler tips, ratings, and more tourist information, refer to the Chicago trip planner .

Singapore, Singapore to Chicago is an approximately 23.5-hour flight. You can also do a combination of flight and train; or do a combination of flight and bus. The time zone changes from Singapore Time (SGT) to Central Standard Time (CST), which is usually a -14 hour difference. Expect slightly colder temperatures when traveling from Singapore in July; daily highs in Chicago reach 33°C and lows reach 22°C. Finish up your sightseeing early on the 17th (Wed) so you can travel to New York City.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Chesterton, Highland Park, Lake Forest, Hawthorn Hollow - Nature Sanctuary and Arboretum, Little Red Schoolhouse
Highlights from your plan
Lincoln Park Zoo ©
Lincoln Park Zoo
The Art Institute of Chicago ©
The Art Institute of Chicago
The Field Museum ©
The Field Museum

15
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Get outdoors at Bronx Zoo and Appalachian Trail - Pochuck Boardwalk. Get a sense of the local culture at Fifth Avenue and 9/11 Memorial. You'll find plenty of places to visit near New York City: Sands Point Preserve (in Port Washington), Sam's Point Preserve (in Cragsmoor) and Angry Orchard (in Walden). The adventure continues: take a stroll through Times Square, grab your bike and head to East River Waterfront Esplanade, identify plant and animal life at Quogue Wildlife Refuge, and don't miss a visit to Central Park.

To find photos, reviews, more things to do, and tourist information, use the New York City road trip planning site .

Traveling by flight from Chicago to New York City takes 5 hours. Alternatively, you can do a combination of flight and train; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In July, daytime highs in New York City are 35°C, while nighttime lows are 26°C. On the 2nd (Fri), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in New York City

Parks Wildlife Outdoors

Side Trips

Valley Cottage, Sands Point Preserve, Demarest Nature Center, Quogue Wildlife Refuge, Wolf Conservation Center
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

Similar Plans

36 days in United States BY A USER FROM AUSTRALIA August, slow & easy, popular & hidden gems PREFERENCES: August ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 37 days in New York City BY A USER FROM UNITED STATES June, culture, museums, fast-paced, popular & hidden gems PREFERENCES: June, culture, museums ATTRACTION STYLE: Popular & hidden gems PACE: Fast-paced 35 days in United States BY A USER FROM AUSTRALIA December, popular & hidden gems PREFERENCES: December ATTRACTION STYLE: Popular & hidden gems PACE: Medium 37 days in Los Angeles & Chicago BY A USER FROM LATVIA June, popular sights PREFERENCES: June ATTRACTION STYLE: Popular sights PACE: Medium 38 days in United States BY A USER FROM AUSTRALIA September, kids, popular sights PREFERENCES: September, kids ATTRACTION STYLE: Popular sights PACE: Medium 51 days in New York City BY A USER FROM BRAZIL March, slow & easy, hidden gems PREFERENCES: March ATTRACTION STYLE: Hidden gems PACE: Slow & easy 4 days in Chicago BY A USER FROM UNITED STATES July, teens, kids, beaches, wildlife, slow & easy, popular & hidden gems PREFERENCES: July, teens, kids, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Slow & easy 40 days in United States BY A USER FROM SWITZERLAND July, teens, hidden gems PREFERENCES: July, teens ATTRACTION STYLE: Hidden gems PACE: Medium 43 days in New York City BY A USER FROM BULGARIA June, popular & hidden gems PREFERENCES: June ATTRACTION STYLE: Popular & hidden gems PACE: Medium 33 days in United States BY A USER FROM ITALY August, kids, outdoors, historic sites, museums, wildlife, slow & easy, popular sights PREFERENCES: August, kids, outdoors, historic sites, museums, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 11 days in Chicago BY A USER FROM UNITED STATES June, teens, kids, slow & easy, hidden gems PREFERENCES: June, teens, kids ATTRACTION STYLE: Hidden gems PACE: Slow & easy 39 days in United States BY A USER FROM UNITED KINGDOM April, slow & easy, hidden gems PREFERENCES: April ATTRACTION STYLE: Hidden gems PACE: Slow & easy
View more plans