23 days in New York City & Illinois Itinerary

23 days in New York City & Illinois Itinerary

Created using Inspirock United States holiday maker

Make it your trip
Fly to La Guardia Airport, Drive to New York City
1
New York City
— 7 nights
Fly
2
Chicago
— 5 nights
Drive
3
Waukegan
— 3 nights
Drive
4
Rockford
— 3 nights
Fly
5
Springfield
— 3 nights
Fly

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New York City

— 7 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
New York City is known for museums, nightlife, and shopping. Your trip includes some of its best attractions: go for a walk through Central Park, make a trip to Grand Central Terminal, stroll around The High Line, and enjoy breathtaking views from Empire State Building.

For ratings, where to stay, photos, and other tourist information, you can read our New York City trip maker site.

Bang Bo, Thailand to New York City is an approximately 27-hour combination of flight and car. You can also do a combination of car and flight. Due to the time zone difference, you'll gain 12 hours traveling from Bang Bo to New York City. Traveling from Bang Bo in July, expect New York City to be slightly colder, temps between 35°C and 26°C. Wrap up your sightseeing on the 8th (Thu) to allow time to fly to Chicago.

Things to do in New York City

Museums · Parks · Historic Sites · Tours

Side Trips

Chicago

— 5 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, nightlife, and parks. Your trip includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, walk around Grant Park, learn about wildlife with up-close encounters at Lincoln Park Zoo, and don't miss a visit to Buckingham Fountain.

For other places to visit, ratings, more things to do, and tourist information, refer to the Chicago trip planner.

You can fly from New York City to Chicago in 4 hours. Alternatively, you can drive; or take a bus. Traveling from New York City to Chicago, you'll gain 1 hour due to the time zone difference. Traveling from New York City in July, expect little chillier with lows of 22°C in Chicago. Finish up your sightseeing early on the 13th (Tue) so you can go by car to Waukegan.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Side Trip

Waukegan

— 3 nights
Waukegan is a city and the county seat of Lake County, Illinois, United States. You'll find plenty of places to visit near Waukegan: Racine (Hot Shop Glass & SC Johnson Headquarters), Kenosha (Hawthorn Hollow - Nature Sanctuary and Arboretum & Southport Light Station Museum) and Chicago Botanic Garden (in Glencoe). There's lots more to do: stroll through Prairie Wolf Slough, take a tour by water with WindyCitySalmon, make a trip to Marytown - The National Shrine of St. Maximilian Kolbe, and bet on a winner at Arlington Park.

To find traveler tips, where to stay, and tourist information, read our Waukegan travel route tool.

Getting from Chicago to Waukegan by car takes about 1.5 hours. Traveling from Chicago in July, expect little chillier with lows of 18°C in Waukegan. Finish up your sightseeing early on the 16th (Fri) so you can go by car to Rockford.

Things to do in Waukegan

Parks · Wildlife · Outdoors · Casinos

Side Trips

Rockford

— 3 nights
Rockford is the third largest city in the U.S. state of Illinois, the 171st most populous city in the United States, the largest city in Illinois outside of the Chicago metropolitan area, and the city of the 148th most populous metropolitan area in the United States. Get out of town with these interesting Rockford side-trips: Whiskey Acres Distilling Co. (in DeKalb), Climbing Tours (in Baraboo) and Janesville (Rotary Botanical Gardens & CAMDEN Playground). There's lots more to do: take in nature's colorful creations at Anderson Japanese Gardens, examine the collection at Historical Auto Attractions, and stroll through Stone Bridge Trail.

To find maps, photos, traveler tips, and other tourist information, go to the Rockford online trip itinerary builder.

Traveling by car from Waukegan to Rockford takes 2 hours. July in Rockford sees daily highs of 33°C and lows of 20°C at night. Finish up your sightseeing early on the 19th (Mon) so you can catch the flight to Springfield.

Things to do in Rockford

Parks · Outdoors · Fun & Games · Tours

Side Trips

Springfield

— 3 nights

Flower City

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Start off your visit on the 20th (Tue): stroll through Lincoln Memorial Garden, then steep yourself in history at Dana-Thomas House, and then take a memorable drive along Great Rivers Scenic Route. On the 21st (Wed), you'll have a packed day of sightseeing: take an in-depth tour of Lincoln Home National Historic Site, get engrossed in the history at The Lincoln Home Visitor Center, then walk around Union Square Park, and finally browse the collection at Abraham Lincoln Presidential Library and Museum.

For other places to visit, where to stay, traveler tips, and more tourist information, read Springfield road trip planning website.

Getting from Rockford to Springfield by flight takes about 3.5 hours. Other options: drive; or do a combination of bus and train. In July, plan for daily highs up to 35°C, and evening lows to 22°C. You will leave for home on the 22nd (Thu).

Things to do in Springfield

Museums · Historic Sites · Scenic Drive · Outdoors

Side Trip

Illinois travel guide

4.4
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.