49 days in Illinois & New York City Itinerary

49 days in Illinois & New York City Itinerary

Created using Inspirock United States tour planner

Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Rockford
1
Rockford
— 5 nights
Fly
2
Peoria
— 3 nights
Drive
3
Springfield
— 5 nights
Drive
4
Alton
— 4 nights
Drive
5
Makanda
— 5 nights
Drive
6
Chicago
— 7 nights
Fly
7
New York City
— 18 nights
Drive to La Guardia Airport, Fly to Monrovia

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Rockford

— 5 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. Explore Rockford's surroundings by going to Whiskey Acres Distilling Co. (in DeKalb), Galena (Grant Park & Blaum Bros. Distilling Co.) and Honey Hill (in Waterman). And it doesn't end there: admire the natural beauty at Anderson Japanese Gardens, examine the collection at Historical Auto Attractions, experience rural life at Selmi's Greenhouse and Farm Market, and stop by Tom's Farm Market and Greenhouse.

To see reviews, other places to visit, where to stay, and more tourist information, read Rockford trip itinerary planner.

Monrovia, Liberia to Rockford is an approximately 25-hour combination of flight and car. You'll gain 6 hours traveling from Monrovia to Rockford due to the time zone difference. In October, Rockford is colder than Monrovia - with highs of 20°C and lows of 7°C. Cap off your sightseeing on the 18th (Mon) early enough to catch the flight to Peoria.

Things to do in Rockford

Parks · Breweries & Distilleries · Museums · Shopping

Side Trips

Peoria

— 3 nights
Explore Peoria's surroundings by going to Ropp Jersey Cheese Farm (in Normal) and Hennepin Canal State Park (in Sheffield).

To find ratings, photos, reviews, and tourist information, use the Peoria journey planner.

Getting from Rockford to Peoria by flight takes about 2.5 hours. Other options: drive; or take a bus. In October, plan for daily highs up to 23°C, and evening lows to 10°C. Finish your sightseeing early on the 21st (Thu) so you can drive to Springfield.

Things to do in Peoria

Parks · Nature · Outdoors · Scenic Drive

Side Trips

Springfield

— 5 nights

Flower City

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Change things up with these side-trips from Springfield: Homer Lake Forest Preserve (in Homer), Champaign County History Museum (in Champaign) and Lake of The Woods County Park (in Mahomet). Next up on the itinerary: stroll through Lincoln Memorial Garden, get lost in a book at Abraham Lincoln Presidential Library and Museum, experience rural life at Hardy's Reindeer Ranch, and let little ones run wild at Washington Park.

To find photos, reviews, more things to do, and other tourist information, read Springfield trip itinerary builder app.

Getting from Peoria to Springfield by car takes about 1.5 hours. Other options: take a bus. In October, plan for daily highs up to 24°C, and evening lows to 9°C. Cap off your sightseeing on the 26th (Tue) early enough to go by car to Alton.

Things to do in Springfield

Parks · Museums · Outdoors · Historic Sites

Side Trips

Alton

— 4 nights
Alton is a city on the Mississippi River in Madison County, Illinois, United States, about 15mi north of St. Change things up with these side-trips from Alton: Schwartz Orchard (in Centralia), Braeutigam Orchards (in Belleville) and Eversgerd’s Civil War Fort (in Germantown). There's much more to do: take a memorable drive along Great Rivers Scenic Route, take an in-depth tour of The 1820 Colonel Benjamin Stephenson House, take in the architecture and atmosphere at First Unitarian Church, and see the interesting displays at World's Tallest Man Statue.

To find maps, reviews, and tourist information, read Alton trip itinerary maker app.

You can drive from Springfield to Alton in 2 hours. In October, plan for daily highs up to 24°C, and evening lows to 9°C. Finish your sightseeing early on the 30th (Sat) so you can travel to Makanda.

Things to do in Alton

Museums · Historic Sites · Outdoors · Parks

Side Trips

Makanda

— 5 nights
Makanda is a village in Jackson County, Illinois, United States. Venture out of the city with trips to Henry N Barkhausen Cache River Wetlands Center (in Cypress) and Vienna (Tunnel Hill State Trail & Mermet Springs Scuba). The adventure continues: surround yourself with nature on Shawnee Bluffs Canopy Tour, learn about winemaking at Alto Vineyards, pause for some photo ops at Bald Knob Cross of Peace, and trek along Shawnee Hills.

For reviews, photos, more things to do, and other tourist information, refer to the Makanda road trip planning site.

You can drive from Alton to Makanda in 2.5 hours. October in Makanda sees daily highs of 25°C and lows of 10°C at night. Finish your sightseeing early on the 4th (Thu) to allow enough time to travel to Chicago.

Things to do in Makanda

Parks · Wineries · Outdoors · Wildlife

Side Trips

Chicago

— 7 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, wander the streets of The Magnificent Mile, take in panoramic vistas at Skydeck Chicago - Willis Tower, and stroll through Millennium Park.

To see more things to do, other places to visit, ratings, and more tourist information, go to the Chicago trip itinerary planner.

Traveling by car from Makanda to Chicago takes 5.5 hours. Alternatively, you can do a combination of car and flight. Traveling from Makanda in November, expect nights in Chicago to be about the same, around 1°C, while days are little chillier, around 11°C. Wrap up your sightseeing on the 11th (Thu) early enough to fly to New York City.

Things to do in Chicago

Museums · Parks · Childrens Museums · Historic Sites

Side Trip

New York City

— 18 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.
Change things up with these side-trips from New York City: Bronx Zoo (in Bronx), Untermyer Gardens (in Yonkers) and Philadelphia (Rodin Museum, Fairmount Water Works Interpretive Education Center, &more). The adventure continues: go for a walk through Central Park, admire the striking features of Rockefeller Center, make a trip to Grand Central Terminal, and stroll through The High Line.

For where to stay, photos, reviews, and more tourist information, read our New York City trip planner.

You can fly from Chicago to New York City in 4 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Chicago to New York City is 1 hour. In November, New York City is somewhat warmer than Chicago - with highs of 16°C and lows of 7°C. Finish your sightseeing early on the 29th (Mon) so you can travel back home.

Things to do in New York City

Museums · Parks · Historic Sites · Tours

Side Trips

Illinois travel guide

4.3
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.