11 days in Chicago & Milwaukee Itinerary

11 days in Chicago & Milwaukee Itinerary

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11 days in Chicago & Milwaukee Itinerary

Start: San Juan, Puerto Rico
Fly:  7​h
1
Chicago
— 5 nights
Drive:  1​h 45​min
2
Milwaukee
— 4 nights
bus + Fly:  9​h 15​min
End: San Juan, Puerto Rico

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your day-by-day itinerary now includes Shedd Aquarium, The Chicago Theatre and 360 Chicago Observation Deck. Satisfy your inner culture vulture at The Magnificent Mile and The Art Institute of Chicago. Take a break from the city and head to Lincoln Park Zoo and Swallow Cliff Stairs. Explore the numerous day-trip ideas around Chicago: Cowles Bog (in Chesterton), Little Red Schoolhouse (in Willow Springs) and Sri Venkateswara Swami Temple (in Aurora). There's still lots to do: appreciate the extensive heritage of Millennium Park, brush up on your knowledge of spirits at Whiskey Acres Distilling Co., look for all kinds of wild species at Prairie Wolf Slough, and don't miss a visit to Cloud Gate.

For more things to do, where to stay, maps, and other tourist information, go to the Chicago trip site .

San Juan, Puerto Rico to Chicago is an approximately 8-hour flight. You can also do a combination of car and flight. The time zone difference moving from Atlantic Standard Time to Central Standard Time is minus 2 hours. Prepare for cooler weather when traveling from San Juan in April: high temperatures in Chicago hover around 59°F and lows are around 40°F. Wrap up your sightseeing on the 9th (Tue) to allow time to take a train to Milwaukee.

Things to do in Chicago

Parks Outdoors Wildlife

Side Trips

Sri Venkateswara Swami Temple, Whiskey Acres Distilling Co., Swallow Cliff Stairs, Deer Grove Forest Preserve, Cowles Bog
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

4
nights
Milwaukee

Milwaukee ©
Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Get some cultural insight at Apple Barn Orchard and Winery and Pieper Porch Winery & Vineyard. Popular historic sites such as Basilica of St. Josaphat and Holy Hill are in your itinerary. Explore Milwaukee's surroundings by going to Spas & Wellness (in Lake Geneva) and Horicon Marsh (in Mayville). There's still lots to do: contemplate the long history of Pabst Mansion, wander the streets of Historic Third Ward, see the interesting displays at Harley-Davidson Museum, and tee off at Moorland Road Golf Center.

To find other places to visit, ratings, where to stay, and other tourist information, read our Milwaukee itinerary website .

Traveling by train from Chicago to Milwaukee takes 1.5 hours. Alternatively, you can drive; or take a bus. Traveling from Chicago in April, you will find days in Milwaukee are little chillier (53°F), and nights are about the same (36°F). Finish your sightseeing early on the 13th (Sat) to allow enough time to travel back home.

Things to do in Milwaukee

Museums Historic Sites Breweries & Distilleries

Side Trips

Horicon Marsh, Historic Greendale Welcome Center, Moorland Road Golf Center, Apple Barn Orchard and Winery, Holy Hill
Highlights from your plan
Horicon Marsh ©
Horicon Marsh
Harley-Davidson Museum ©
Harley-Davidson Museum
Milwaukee Art Museum ©
Milwaukee Art Museum

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