31 days in Milwaukee, Chicago & New York City Itinerary

31 days in Milwaukee, Chicago & New York City Itinerary

Created using Inspirock United States trip planner
Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Milwaukee
1
Milwaukee
— 9 nights
Drive
2
Chicago
— 7 nights
Fly
3
New York City
— 13 nights
Drive to La Guardia Airport, Fly to Vijayawada

S M T W T F S
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1

Milwaukee — 9 nights

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
You'll find plenty of places to visit near Milwaukee: Bookworm Gardens (in Sheboygan), Road America (in Elkhart Lake) and Madison (Olbrich Botanical Gardens & Memorial Union Terrace). There's still lots to do: take an in-depth tour of Portage WWII History Museum, take a peaceful walk through Hawthorn Hollow - Nature Sanctuary and Arboretum, stroll through Atwater Park & Beach, and admire the landmark architecture of SC Johnson Headquarters.

To find where to stay, traveler tips, ratings, and tourist information, you can read our Milwaukee travel planner.

Vijayawada, India to Milwaukee is an approximately 25-hour combination of flight and car. Traveling from Vijayawada to Milwaukee, you'll gain 11.5 hours due to the time zone difference. In September, Milwaukee is a bit cooler than Vijayawada - with highs of 27°C and lows of 17°C. Wrap up your sightseeing on the 10th (Sat) to allow time to drive to Chicago.
more
Parks · Outdoors · Museums · Beaches
Side Trips

Chicago — 7 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Take a break from Chicago with a short trip to Chicago Botanic Garden in Glencoe, about 34 minutes away. And it doesn't end there: admire the masterpieces at The Art Institute of Chicago, stroll through Millennium Park, ponder the design of Buckingham Fountain, and get up close and personal with brilliant marine life at Shedd Aquarium.

To see more things to do, ratings, where to stay, and tourist information, read Chicago road trip planning tool.

Traveling by car from Milwaukee to Chicago takes 1.5 hours. Alternatively, you can take a train; or take a bus. In September, daily temperatures in Chicago can reach 30°C, while at night they dip to 19°C. Finish up your sightseeing early on the 17th (Sat) so you can catch the flight to New York City.
more
Parks · Museums · Childrens Museums · Tours
Side Trips

New York City — 13 nights

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Get out of town with these interesting New York City side-trips: Philadelphia (Christ Church, Wissahickon Valley Park, &more) and Coney Island (in Brooklyn). Next up on the itinerary: don't miss a visit to Central Park, go for a walk through Times Square, appreciate the history behind Statue of Liberty National Monument, and stroll around The High Line.

To find where to stay, reviews, maps, and tourist information, use the New York City attractions planner.

Traveling by flight from Chicago to New York City takes 4 hours. Alternatively, you can drive; or take a bus. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. September in New York City sees daily highs of 31°C and lows of 22°C at night. Finish up your sightseeing early on the 30th (Fri) so you can travel back home.
more
Parks · Museums · Historic Sites · Shopping
Side Trips