31 days in Chicago and Beyond, Orlando & New York City Itinerary

31 days in Chicago and Beyond, Orlando & New York City Itinerary

Created using Inspirock United States journey planner
Make it your trip
Fly
1
Chicago
— 5 nights
Drive
2
Ottawa
— 1 night
Drive
3
Rockford
— 4 nights
Fly
4
Orlando
— 7 nights
Fly
5
New York City
— 12 nights
Fly

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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 sightseeing, museums, and nightlife. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, meet the residents at Lincoln Park Zoo, ponder the design of Buckingham Fountain, and engage your brain at Museum of Science and Industry.

To see traveler tips, maps, ratings, and more tourist information, read Chicago road trip planner.

Manila, Philippines to Chicago is an approximately 22-hour flight. Due to the time zone difference, you'll gain 14 hours traveling from Manila to Chicago. Prepare for little chillier weather when traveling from Manila in July: high temperatures in Chicago hover around 33°C and lows are around 22°C. Cap off your sightseeing on the 3rd (Tue) early enough to go by car to Ottawa.
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Museums · Parks · Childrens Museums · Zoos & Aquariums
Side Trip

Ottawa — 1 night

Ottawa is a city located at the confluence of the navigable Illinois River and Fox River in LaSalle County, Illinois, United States. Kick off your visit on the 4th (Wed): admire the majestic nature at Matthiessen State Park, see the interesting displays at Reddick Mansion and Gardens, then stroll around Washington Square Park, and finally relax and rejuvenate at SaltTreeYoga.

For photos, traveler tips, other places to visit, and other tourist information, use the Ottawa day trip planner.

You can drive from Chicago to Ottawa in 1.5 hours. Traveling from Chicago in August, plan for slightly colder nights in Ottawa, with lows around 19°C. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Rockford.
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Parks · Museums · Nature · Spas
Side Trip

Rockford — 4 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. You'll find plenty of places to visit near Rockford: The Eagle's Nest Art Colony Collection (in Oregon), Freeport (Jane Addams Recreation Trail, Oscar Taylor Home, &more) and Dixon (The Next Picture Show, Old Settlers Memorial Cabin, &more). There's much more to do: experience rural life at Whiskey Acres Distilling Co., learn about all things military at Historic Auto Attractions, admire the natural beauty at Anderson Japanese Gardens, and trek along Stone Bridge Trail.

To see other places to visit, photos, reviews, and tourist information, read Rockford road trip planning website.

You can drive from Ottawa to Rockford in 1.5 hours. Another option is to drive. August in Rockford sees daily highs of 32°C and lows of 19°C at night. Wrap up your sightseeing on the 8th (Sun) to allow time to fly to Orlando.
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Parks · Trails · Museums · Outdoors
Side Trips

Orlando — 7 nights

Theme Park Capital of the World

For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Pack the 10th (Tue) with family-friendly diversions at Universal's Islands of Adventure. Pack the 11th (Wed) with family-friendly diversions at Universal Orlando Resort. There's still lots to do: discover the magic at Magic Kingdom Park, get in on the family fun at Epcot, cool off at Disney's Typhoon Lagoon Water Park, and stroll around Mako.

For more things to do, where to stay, reviews, and tourist information, read Orlando road trip planning site.

Fly from Rockford to Orlando in 5 hours. Alternatively, you can drive; or take a bus. You'll lose 1 hour traveling from Rockford to Orlando due to the time zone difference. Traveling from Rockford in August, things will get somewhat warmer in Orlando: highs are around 39°C and lows about 28°C. Finish your sightseeing early on the 15th (Sun) so you can fly to New York City.
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Theme Parks · Golf · Outdoors · Fun & Games

New York City — 12 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.
You'll find plenty of places to visit near New York City: Bronx Zoo (in Bronx) and Coney Island (in Brooklyn). There's still lots to do: take in the pleasant sights at Central Park, walk around The High Line, take a stroll through Times Square, and admire the striking features of Empire State Building.

To see traveler tips, where to stay, more things to do, and more tourist information, you can read our New York City trip maker app.

Traveling by flight from Orlando to New York City takes 4.5 hours. Alternatively, you can drive; or take a bus. Traveling from Orlando in August, expect New York City to be little chillier, temps between 34°C and 25°C. Finish your sightseeing early on the 27th (Fri) to allow enough time to fly back home.
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Parks · Museums · Historic Sites · Zoos & Aquariums
Side Trips