9 days in Brooklyn, Chicago & Rapid City Itinerary

9 days in Brooklyn, Chicago & Rapid City Itinerary

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Route & dates

9 days in Brooklyn, Chicago & Rapid City Itinerary

Start: Newark
Drive:  45​min
1
Brooklyn
— 2 nights
bus + Fly:  4​h 45​min
2
Chicago
— 1 night
Fly:  4​h 45​min
3
Rapid City
— 5 nights
Fly:  7​h 45​min
End: Newark

2
nights
Brooklyn

Brooklyn ©
Though it may be less popular or touristy than its big brother Manhattan, Brooklyn boasts of one of the largest and hippest art districts in the United States.
Get outdoors at Jenkinson's Boardwalk and Orange County Arboretum. Explore hidden gems such as Storm King Art Center and Wertheim National Wildlife Refuge. Go for a jaunt from Brooklyn to Mastic Beach to see William Floyd Estate about 1h 30 min away. There's more to do: get to know the fascinating history of Brooklyn Heights Promenade.

To find out how to plan a trip to Brooklyn, use our trip itinerary maker.

Newark to Brooklyn is an approximately 1-hour car ride. In June in Brooklyn, expect temperatures between 80°F during the day and 65°F at night. Wrap up your sightseeing on the 1st (Sun) to allow time to travel to Chicago.

Things to do in Brooklyn

Parks Wildlife Historic Sites

Side Trips

Storm King Art Center, William Floyd Estate, Wertheim National Wildlife Refuge, Orange County Arboretum, Jenkinson's Boardwalk
Highlights from your plan
Storm King Art Center ©
Storm King Art Center
William Floyd Estate ©
William Floyd Estate
Wertheim National Wildlife Refuge ©

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 2nd (Mon): don't miss a visit to Buckingham Fountain, explore the activities along Lake Michigan, then appreciate the extensive heritage of Chicago Riverwalk, and finally admire the striking features of Chicago Cultural Center.

To find other places to visit, traveler tips, more things to do, and tourist information, go to the Chicago trip maker .

You can do a combination of train and flight from Brooklyn to Chicago in 5 hours. Alternatively, you can do a combination of subway, bus, and flight; or drive. The time zone difference when traveling from Brooklyn to Chicago is minus 1 hour. Traveling from Brooklyn in July, expect little chillier with lows of 67°F in Chicago. Finish your sightseeing early on the 2nd (Mon) to allow enough time to travel to Rapid City.

Things to do in Chicago

Nature Parks Historic Sites

Side Trip

Lake Michigan
Highlights from your plan
Lake Michigan ©
Lake Michigan
Buckingham Fountain ©
Buckingham Fountain
Chicago Cultural Center ©
Chicago Cultural Center

5
nights
Rapid City

Rapid City ©
South Dakota's second-largest city, Rapid City has for many years served as a gateway to the West.
Museum-lovers will appreciate South Dakota Air and Space Museum and National Presidential Wax Museum. Escape the urban bustle at Wind Cave National Park and Needles Eye Tunnel. Change things up with these side-trips from Rapid City: Badlands National Park (Panorama Point Overlook, Loop Road, & more), Presidential Trail (in Keystone) and Custer (Iron Mountain Road & Sylvan Lake). There's lots more to do: explore the different monuments and memorials at Mount Moriah Cemetery, get engrossed in the history at Adams House, take in the exciting artwork at Suzie Cappa Art Center, and meet the residents at Reptile Gardens.

To find other places to visit, photos, more things to do, and other tourist information, read our Rapid City itinerary planning site .

Traveling by flight from Chicago to Rapid City takes 5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Chicago to Rapid City. Expect little chillier evenings in Rapid City when traveling from Chicago in July, with lows around 62°F. Wrap up your sightseeing by early afternoon on the 7th (Sat) to allow time for travel back home.

Things to do in Rapid City

Parks Nature Outdoors

Side Trips

Custer, Badlands National Park, Keystone, Deadwood, Wind Cave National Park
Highlights from your plan
Badlands Wall ©
Badlands Wall
Wind Cave National Park ©
Wind Cave National Park
National Presidential Wax Museum ©
National Presidential Wax Museum

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