29 days in Chicago, North Carolina & New York City Itinerary

29 days in Chicago, North Carolina & New York City Itinerary

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Route & dates

29 days in Chicago, North Carolina & New York City Itinerary

Start: Doha
Fly:  17​h 15​min
1
Chicago
— 3 nights
Fly:  4​h
2
Pisgah Forest
— 3 nights
Drive:  2​h 30​min
3
Blowing Rock
— 4 nights
Drive:  2​h
4
Charlotte
— 4 nights
Fly + Taxi:  3​h 30​min
5
Beaufort
— 3 nights
Drive:  3​h 15​min
6
Raleigh
— 4 nights
Fly + Bus:  4​h 30​min
7
New York City
— 6 nights
Fly:  17​h 45​min
End: Doha

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Do some cultural sightseeing at The Art Institute of Chicago and Millennium Park. Ernest Hemingway Birthplace and Fourth Presbyterian Church will appeal to history buffs. Get out of town with these interesting Chicago side-trips: Little Red Schoolhouse (in Willow Springs), Busse Woods Trail System (in Elk Grove Village) and Swallow Cliff Stairs (in Palos Park). The adventure continues: make a trip to The Magnificent Mile, admire the striking features of Rockefeller Memorial Chapel, take in the exciting artwork at Chicago Cultural Center, and examine the collection at Swedish American Museum.

You can plan Chicago trip in no time by asking Inspirock to help create your itinerary.

Doha, Qatar to Chicago is an approximately 17.5-hour flight. The time zone changes from Arabia Standard Time to Central Standard Time, which is usually a -9 hour difference. Expect much colder temperatures when traveling from Doha in October; daily highs in Chicago reach 21°C and lows reach 11°C. Finish your sightseeing early on the 20th (Sun) to allow enough time to travel to Pisgah Forest.

Things to do in Chicago

Parks Wildlife Outdoors

Side Trips

Busse Woods Trail System, Swallow Cliff Stairs, Ernest Hemingway Birthplace, Little Red Schoolhouse
Highlights from your plan
Millennium Park ©
Millennium Park
The Art Institute of Chicago ©
The Art Institute of Chicago
Ernest Hemingway Birthplace ©
Ernest Hemingway Birthplace

3
nights
Pisgah Forest

Pisgah Forest is an unincorporated community in Transylvania County, North Carolina, United States. Escape the urban bustle at DuPont State Recreational Forest and Dry Falls. Venture out of the city with trips to Slick Rock Country Emporium (in Hendersonville) and Zipline (in Lake Lure). Make the 22nd (Tue) an awe-inspiring day at Pisgah National Forest. The adventure continues: take in the awesome beauty at Whiteside Mountain.

For traveler tips, maps, ratings, and tourist information, use the Pisgah Forest journey app .

Getting from Chicago to Pisgah Forest by flight takes about 4 hours. Other options: do a combination of flight and car; or drive. Traveling from Chicago to Pisgah Forest, you'll lose 1 hour due to the time zone difference. In October, plan for daily highs up to 24°C, and evening lows to 9°C. Finish your sightseeing early on the 23rd (Wed) to allow enough time to drive to Blowing Rock.

Things to do in Pisgah Forest

Parks Nature Outdoors

Side Trips

Zipline, Dry Falls, Slick Rock Country Emporium, DuPont State Recreational Forest, Whiteside Mountain
Highlights from your plan
Zipline
DuPont State Recreational Forest ©
DuPont State Recreational Forest
Pisgah National Forest ©
Pisgah National Forest

4
nights
Blowing Rock

Blowing Rock ©
Blowing Rock is a town in Watauga and Caldwell counties in the U.S. Head to Mountain Dog and Caldwell Arts Councilfor plenty of shopping. Visiting Blue Ridge Pkwy and Fishing Charters & Tours will get you outdoors. Explore the numerous day-trip ideas around Blowing Rock: Lenoir Greenway (in Lenoir), Cascades Falls (in Wilkesboro) and Rough Ridge Lookout (in Linville). There's lots more to do: take in the awesome beauty at Grandfather Mountain, identify plant and animal life at Turtle Island Preserve, explore the landscape on two wheels at Catawba River Greenway, and admire the sheer force of Bobby McLean Memorial Park.

Plan my Blowing Rock trip by asking Inpirock to come up with tips and suggestions.

You can drive from Pisgah Forest to Blowing Rock in 2.5 hours. Alternatively, you can do a combination of car and bus; or take a bus. While traveling from Pisgah Forest, expect slightly colder days and about the same nights in Blowing Rock, ranging from highs of 20°C to lows of 7°C. Finish your sightseeing early on the 27th (Sun) to allow enough time to drive to Charlotte.

Things to do in Blowing Rock

Parks Wildlife Outdoors

Side Trips

Lenoir, Linville, Boone, Cascades Falls, Bobby McLean Memorial Park
Highlights from your plan
Grandfather Mountain ©
Grandfather Mountain
Turtle Island Preserve ©
Turtle Island Preserve
Blue Ridge Pkwy ©
Blue Ridge Pkwy

4
nights
Charlotte

Charlotte ©
A rapidly growing city in central North Carolina, Charlotte is the state's largest urban center and a major regional hub for finance, industry, technology, and entertainment.
Your inner history buff will appreciate Kings Mountain National Military Park and Cowpens National Battlefield. Escape the urban bustle at Falls Park on the Reedy and Buzzard Rock Trail. Explore the numerous day-trip ideas around Charlotte: Kings Mountain Gateway Trail (in Kings Mountain), Broad River Greenway (in Boiling Springs) and Fisher Farm (in Davidson). Next up on the itinerary: stroll through Reedy Creek Nature Center and Preserve, identify plant and animal life at Latta Plantation Nature Center & Preserve, and look for gifts at PuckerButt Pepper Company.

Find out how to plan Charlotte trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Blowing Rock to Charlotte takes 2 hours. Alternatively, you can take a bus. Traveling from Blowing Rock in October, expect Charlotte to be somewhat warmer, temps between 28°C and 12°C. Wrap up your sightseeing on the 31st (Thu) to allow time to travel to Beaufort.

Things to do in Charlotte

Parks Nature Outdoors

Side Trips

Huntersville, Cowpens National Battlefield, Falls Park on the Reedy, Kings Mountain Gateway Trail, Fisher Farm
Highlights from your plan
Falls Park on the Reedy ©
Falls Park on the Reedy
Kings Mountain National Military Park ©
Cowpens National Battlefield ©
Cowpens National Battlefield

3
nights
Beaufort

Beaufort ©
Beaufort is a town in and the county seat of Carteret County, North Carolina, United States. For shopping fun, head to Fine Art at Baxters or Beaufort Olive Oil Company. Visiting Cape Lookout National Seashore and Stand-Up Paddleboarding will get you outdoors. Venture out of the city with trips to Possumwood Acres Wildlife Sanctuary (in Hubert) and Pine Cliffs Recreation Area - Neusiok Trail (in Havelock). Next up on the itinerary: admire the majestic nature at Fort Macon State Park, get around town with Island Express Ferry Service, and head outdoors with Beaufort Paddle.

To find other places to visit, maps, traveler tips, and tourist information, use the Beaufort trip planner.

You can do a combination of flight and taxi from Charlotte to Beaufort in 3.5 hours. Other options are to do a combination of flight and car; or drive. Expect somewhat warmer evenings in Beaufort when traveling from Charlotte in October, with lows around 17°C. Finish your sightseeing early on the 3rd (Sun) so you can drive to Raleigh.

Things to do in Beaufort

Parks Outdoors Tours

Side Trips

Pine Cliffs Recreation Area - Neusiok Trail, Stand-Up Paddleboarding, Possumwood Acres Wildlife Sanctuary, Cape Lookout National Seashore, Fine Art at Baxters
Highlights from your plan
Island Express Ferry Service ©
Island Express Ferry Service
Cape Lookout National Seashore ©
Cape Lookout National Seashore
Possumwood Acres Wildlife Sanctuary ©

4
nights
Raleigh

Raleigh ©
For those not from the South, Raleigh might be one of the region's better-kept travel secrets.
Get in touch with nature at Conservators Center and Sylvan Heights Bird Park. You'll find plenty of places to visit near Raleigh: Hawk Manor Falconry (in Lillington), Alpaca Dreams (in Louisburg) and Cedar Creek Gallery & Pottery (in Creedmoor). There's still lots to do: look for all kinds of wild species at Blind Cat Rescue & Sanctuary, tour the pleasant surroundings at Tar River Trail, trek along Neuse River Trail, and explore the landscape on two wheels at Clayton River Walk.

To see ratings, photos, other places to visit, and tourist information, refer to the Raleigh trip builder tool .

Traveling by car from Beaufort to Raleigh takes 3.5 hours. Alternatively, you can do a combination of bus and train; or take a bus. Traveling from Beaufort in November, Raleigh is a bit cooler at night with lows of 4°C. Finish up your sightseeing early on the 7th (Thu) so you can travel to New York City.

Things to do in Raleigh

Parks Wildlife Outdoors

Side Trips

Cedar Creek Gallery & Pottery, Clayton River Walk, Hawk Manor Falconry, Alpaca Dreams, Tar River Trail
Highlights from your plan
Sylvan Heights Bird Park ©
Sylvan Heights Bird Park
Conservators Center ©
Conservators Center
Blind Cat Rescue & Sanctuary ©
Blind Cat Rescue & Sanctuary

6
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.
Museum-lovers will get to explore 9/11 Memorial and Ellis Island. Head to Fifth Avenue and Tiles For Americafor plenty of shopping. Go for a jaunt from New York City to Oceanville to see Edwin B. Forsythe National Wildlife Refuge about 1h 55 min away. Next up on the itinerary: make a trip to The Metropolitan Museum of Art, take in the architecture and atmosphere at St. Patrick's Cathedral, grab your bike and head to East River Waterfront Esplanade, and go for a walk through Times Square.

To find where to stay, traveler tips, more things to do, and more tourist information, read our New York City trip itinerary builder .

Getting from Raleigh to New York City by combination of flight and bus takes about 4.5 hours. Other options: fly; or drive. Traveling from Raleigh in November, expect nights in New York City to be about the same, around 7°C, while days are little chillier, around 16°C. Wrap up your sightseeing on the 13th (Wed) early enough to travel back home.

Things to do in New York City

Parks Museums Historic Sites

Side Trip

Edwin B. Forsythe National Wildlife Refuge
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 ©

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