20 days in Great Lakes USA Itinerary

Created using Inspirock Great Lakes USA holiday planner
Make it your trip
Fly
1
Holland
— 2 nights
Fly
2
Chicago
— 5 nights
Fly
3
Springfield
— 4 nights
Drive
4
Galena
— 2 nights
Fly
5
Milwaukee
— 3 nights
Fly
6
Dayton
— 3 nights
Fly

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Holland — 2 nights

Deepen your sense of the past at sights like Grand Haven Lighthouse and Pier and Central Avenue Christian Reformed Church. Fenn Valley Vineyards and Muskegon South Pierhead Lighthouse are good opportunities to explore the local culture. Get out of town with these interesting Holland side-trips: Bell's Comstock Brewery (in Galesburg), Silver Lake State Park Pedestrian Dune Access (in Hart) and Silver Beach County Park (in Saint Joseph).

To see photos, ratings, maps, and more tourist information, use the Holland attractions planning tool.

Philadelphia to Holland is an approximately 4-hour flight. You can also drive; or do a combination of train and bus. Plan for little chillier temperatures traveling from Philadelphia in May, with highs in Holland at 69°F and lows at 49°F. Wrap up your sightseeing on the 3rd (Wed) early enough to fly to Chicago.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips

Chicago — 5 nights

Windy City

Get some cultural insight at The Art Institute of Chicago and Frank Lloyd Wright Home and Studio. Get in touch with nature at Boat Tours & Water Sports and Kathy Osterman Beach. Explore the numerous day-trip ideas around Chicago: Rosewood Beach (in Highland Park), Shrine of the Christ's Passion (in Saint John) and Basilica of the Sacred Heart (in South Bend). There's still lots to do: take in the spiritual surroundings of Frank Lloyd Wright's Unity Temple, don't miss a visit to The Magnificent Mile, take in panoramic vistas at Skydeck Chicago - Willis Tower, and contemplate the long history of Pleasant Home.

To see where to stay, photos, other places to visit, and tourist information, use the Chicago vacation builder.

Getting from Holland to Chicago by flight takes about 2.5 hours. Other options: drive; or take a train. You'll gain 1 hour traveling from Holland to Chicago due to the time zone difference. In May, daily temperatures in Chicago can reach 71°F, while at night they dip to 52°F. Finish your sightseeing early on the 8th (Mon) to allow enough time to fly to Springfield.
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Historic Sites · Outdoors · Parks · Beaches
Side Trips

Springfield — 4 nights

Flower City

Do some cultural sightseeing at Dana-Thomas House and Old State Capitol. Deepen your sense of the past at sights like Lincoln Home National Historic Site and Lincolns New Salem State Park. You'll find plenty of places to visit near Springfield: Mount Pulaski Courthouse State Historic Site (in Mount Pulaski), Funks Grove Church & Chapel in the Trees (in McLean) and Lake Shelbyville (in Shelbyville). Next up on the itinerary: identify plant and animal life at Lincoln Memorial Garden, steep yourself in history at Edwards Place Historic Home, pause for some serene contemplation at Cathedral of the Immaculate Conception, and explore the different monuments and memorials at Camp Butler National Cemetery.

To see more things to do, reviews, and other tourist information, read Springfield trip planner.

Traveling by flight from Chicago to Springfield takes 2.5 hours. Alternatively, you can drive; or take a train. In May, plan for daily highs up to 76°F, and evening lows to 55°F. Cap off your sightseeing on the 12th (Fri) early enough to go by car to Galena.
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Historic Sites · Museums · Parks · Outdoors
Side Trips

Galena — 2 nights

On the 13th (Sat), appreciate the extensive heritage of Root Beer Revelry, then steep yourself in history at Washburne House State Historic Site, then steep yourself in history at Ulysses S. Grant Home, and finally sample the fine beverages at Blaum Bros. Distilling Co.. Here are some ideas for day two: look for gifts at Galena / Jo Daviess County Historical Society and Museum, then contemplate the long history of Heritage Canyon, and then contemplate the long history of De Immigrant Windmill.

To see more things to do, ratings, and more tourist information, go to the Galena sightseeing planner.

You can drive from Springfield to Galena in 4.5 hours. Other options are to do a combination of train and flight; or fly. Prepare for a bit cooler weather when traveling from Springfield in May: high temperatures in Galena hover around 69°F and lows are around 48°F. Finish up your sightseeing early on the 14th (Sun) so you can catch the flight to Milwaukee.
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Historic Sites · Breweries & Distilleries · Shopping · Museums
Side Trip

Milwaukee — 3 nights

Brew City

Your itinerary includes some good beach time at Atwater Park & Beach and Sandy Beach. Get a sense of the local culture at Basilica of St. Josaphat and Holy Hill. Get out of town with these interesting Milwaukee side-trips: Bartel's Beach (in Lake Mills), Horicon Marsh (in Mayville) and North Beach Park (in Racine).

Before you visit Milwaukee, use our trip planner to discover what you can do and see there.

Fly from Galena to Milwaukee in 3 hours. Alternatively, you can drive; or take a bus. In May, plan for daily highs up to 66°F, and evening lows to 47°F. Cap off your sightseeing on the 17th (Wed) early enough to catch the flight to Dayton.
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Parks · Outdoors · Beaches · Historic Sites
Side Trips

Dayton — 3 nights

Gem City

Carillon Historical Park and National Museum of the US Air Force are good opportunities to explore the local culture. Visit Dayton Aviation Heritage National Historical Park and SunWatch Indian Village/Archaeological Park for their historical value. The adventure continues: explore the different monuments and memorials at Woodland Cemetery & Arboretum, deepen your knowledge of military history at Dayton National Cemetery, take in nature's colorful creations at Wegerzyn Gardens MetroPark, and look for all kinds of wild species at Aullwood Audubon.

To see reviews, maps, where to stay, and tourist information, read Dayton travel planner.

You can fly from Milwaukee to Dayton in 3 hours. Other options are to drive; or do a combination of train and bus. The time zone difference when traveling from Milwaukee to Dayton is 1 hour. Prepare for a bit warmer weather when traveling from Milwaukee in May: high temperatures in Dayton hover around 74°F and lows are around 53°F. Finish your sightseeing early on the 20th (Sat) to allow enough time to fly back home.
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Historic Sites · Parks · Nature · Museums
Side Trip