60 days in Chicago & Houston Itinerary

60 days in Chicago & Houston Itinerary

Created using Inspirock United States holiday planner

Make it your trip
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Chicago
— 46 nights
Fly
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Houston
— 13 nights
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Chicago

— 46 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Escape the urban bustle at Lakefront Trail and Starved Rock State Park. You'll explore the less-touristy side of things at Chicago Riverwalk and Milwaukee Art Museum. Explore Chicago's surroundings by going to Grand Mere State Park (in Stevensville), South Haven (Michigan Maritime Museum, Kal Haven Trail, &more) and Saint Joseph (Silver Beach County Park, Krasl Art Center, &more). Spend the 30th (Mon) exploring nature at Indiana Dunes National Park. Next up on the itinerary: browse the exhibits of Studebaker National Museum, admire the landmark architecture of Baha'i House of Worship, contemplate in the serene atmosphere at Holy Name Cathedral, and add some adventure to your tour with a kayaking and canoeing tour.

For traveler tips and more tourist information, refer to the Chicago trip planner.

Montevideo, Uruguay to Chicago is an approximately 16.5-hour flight. The time zone difference when traveling from Montevideo to Chicago is minus 3 hours. While traveling from Montevideo, expect a bit warmer days and warmer nights in Chicago, ranging from highs of 33°C to lows of 22°C. Finish your sightseeing early on the 2nd (Sat) to allow enough time to fly to Houston.

Things to do in Chicago

Parks · Historic Sites · Museums · Outdoors

Side Trips

Houston

— 13 nights

Bayou City

Although urban sprawl remains synonymous with Houston, most of the city's tourist attractions lie within the relatively small downtown area, surrounded by diverse neighborhoods housing the nation's biggest African-American, Asian-American, and Latino communities.
Popular historic sites such as 1892 Bishop's Palace and San Jacinto Battleground State Historic Site are in your itinerary. Satisfy your inner culture vulture at Museum of Fine Arts, Houston and The Menil Collection. You'll find plenty of places to visit near Houston: Brazos Bend State Park (in Needville), Battleship Texas State Historic Site (in La Porte) and Galveston (Galveston Historic Seaport - Home of the 1877 Tall Ship ELISSA, Fishing Charters & Tours, &more). There's much more to do: get engrossed in the history at Holocaust Museum Houston, have fun and explore at Children's Museum Houston, see the interesting displays at Texas Prison Museum, and explore the different monuments and memorials at Glenwood Cemetery.

Planning Houston trip won't be overwhelming when you use Inspirock's itinerary maker.

Fly from Chicago to Houston in 4.5 hours. Alternatively, you can drive; or do a combination of train and bus. In October, Houston is a bit warmer than Chicago - with highs of 34°C and lows of 22°C. Finish up your sightseeing early on the 15th (Fri) so you can catch the flight back home.

Things to do in Houston

Museums · Parks · Historic Sites · Outdoors

Side Trips