22 days in Chicago, Milwaukee & New York City Itinerary

22 days in Chicago, Milwaukee & New York City Itinerary

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Route & dates

22 days in Chicago, Milwaukee & New York City Itinerary

Start: Curitiba
Fly:  16​h 30​min
1
Chicago
— 6 nights
Train:  1​h 30​min
2
Milwaukee
— 6 nights
Fly:  5​h 30​min
3
New York City
— 8 nights
Fly:  16​h 15​min
End: Curitiba

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, appreciate the extensive heritage of Millennium Park, get curious at Museum of Science and Industry, Chicago, and admire nature's wide array of creatures at Shedd Aquarium.

For traveler tips, maps, other places to visit, and tourist information, read our Chicago online road trip planner .

Curitiba, Brazil to Chicago is an approximately 16.5-hour flight. You can also do a combination of bus, taxi, and flight. The time zone difference when traveling from Curitiba to Chicago is minus 3 hours. Traveling from Curitiba in July, expect Chicago to be a bit warmer, temps between 34°C and 23°C. Wrap up your sightseeing on the 26th (Thu) to allow time to take a train to Milwaukee.

Things to do in Chicago

Parks Museums Childrens Museums
Highlights from your plan
Shedd Aquarium ©
Shedd Aquarium
The Art Institute of Chicago ©
The Art Institute of Chicago
Wrigley Field ©
Wrigley Field

6
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Change things up with these side-trips from Milwaukee: Road America (in Elkhart Lake), Horicon Marsh (in Mayville) and Bookworm Gardens (in Sheboygan). And it doesn't end there: tee off at Whistling Straits Golf Course - Straits and Irish, hunt for treasures at Milwaukee Public Market, get a sense of history and politics at Wisconsin State Capitol, and let the kids burn off some steam at CAMDEN Playground.

To see photos, where to stay, ratings, and other tourist information, use the Milwaukee travel planner.

You can take a train from Chicago to Milwaukee in 1.5 hours. Other options are to drive; or take a bus. Traveling from Chicago in July, expect nights in Milwaukee to be about the same, around 20°C, while days are little chillier, around 31°C. Wrap up your sightseeing by early afternoon on the 1st (Wed) to allow time for travel to New York City.

Things to do in Milwaukee

Parks Outdoors Fun & Games

Side Trips

Madison, Bookworm Gardens, Road America, CAMDEN Playground, Sharon Lynne Wilson Center for the Arts
Highlights from your plan
Bookworm Gardens ©
Bookworm Gardens
Road America ©
Road America
Olbrich Botanical Gardens ©
Olbrich Botanical Gardens

8
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.
Change things up with a short trip to Bronx Zoo in Bronx (about 42 minutes away). There's lots more to do: go for a walk through Central Park, take in panoramic vistas at Top of the Rock Observation Deck, admire the striking features of Grand central terminal, and make a trip to Empire State Building.

To see photos, other places to visit, traveler tips, and tourist information, read New York City trip planner .

Getting from Milwaukee to New York City by flight takes about 5.5 hours. Other options: do a combination of flight and train; or drive. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. Traveling from Milwaukee in August, New York City is a bit warmer at night with lows of 26°C. Wrap up your sightseeing on the 9th (Thu) early enough to travel back home.

Things to do in New York City

Museums Parks Historic Sites

Side Trip

Bronx Zoo
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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