11 days in Chicago, Apple Valley & Wisconsin Itinerary

11 days in Chicago, Apple Valley & Wisconsin Itinerary

Created using Inspirock United States route planner
Make it your trip
— 4 nights
Fly to Minneapolis–Saint Paul International Airport / Wold–Chamberlain Field, Drive to Apple Valley
Apple Valley
— 1 night
Drive to Minneapolis–Saint Paul International Airport / Wold–Chamberlain Field, Fly to Chicago O'Hare International Airport, Drive to Milwaukee
— 1 night
Wisconsin Dells
— 3 nights
Train to S6 & Clybourn, Fly to Denver


Chicago — 4 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for sightseeing, museums, and nightlife. Your trip includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, meet the residents at Shedd Aquarium, get a new perspective on things with Boat Tours & Water Sports, and walk around Millennium Park.

Plan a trip to Chicago easily and quickly by telling Inspirock to suggest an itinerary.

Denver to Chicago is an approximately 4.5-hour flight. You can also drive; or take a train. Traveling from Denver to Chicago, you'll lose 1 hour due to the time zone difference. Traveling from Denver in August, plan for somewhat warmer nights in Chicago, with lows around 67°F. Wrap up your sightseeing on the 14th (Sun) early enough to travel to Apple Valley.
Museums · Parks · Childrens Museums · Zoos & Aquariums

Apple Valley — 1 night

Apple Valley is a city in northwestern Dakota County in the State of Minnesota, and a suburb of the Twin Cities. Start off your visit on the 14th (Sun): admire the sheer force of Vermillion Falls and then learn about winemaking at Cannon River Winery. Here are some ideas for day two: get to know the resident critters at Minnesota Zoo.

To see photos, other places to visit, and more tourist information, go to the Apple Valley travel itinerary planner.

Use the Route module to find suitable travel options from Chicago to Apple Valley. Traveling from Chicago in August, expect Apple Valley to be little chillier, temps between 77°F and 57°F. Wrap up your sightseeing by early afternoon on the 15th (Mon) to allow time for travel to Milwaukee.
Parks · Nature · Zoos & Aquariums · Wineries
Side Trips

Milwaukee — 1 night

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Kick off your visit on the 16th (Tue): admire the natural beauty at Lynden Sculpture Garden, then meet the residents at Milwaukee County Zoo, and then examine the collection at Harley-Davidson Museum.

To see ratings, maps, more things to do, and more tourist information, refer to the Milwaukee trip planner.

Explore your travel options from Apple Valley to Milwaukee with the Route module. Traveling from Apple Valley in August, plan for a bit warmer nights in Milwaukee, with lows around 64°F. Cap off your sightseeing on the 16th (Tue) early enough to go by car to Wisconsin Dells.
Museums · Parks · Zoos & Aquariums

Wisconsin Dells — 3 nights

Named after a nearby scenic gorge famous for its steep sandstone formations, Wisconsin Dells features more than 20 water parks, making it one of the most popular vacation areas in this region.
Take a break from Wisconsin Dells with a short trip to Olbrich Botanical Gardens in Madison, about 1h 5 min away. Next up on the itinerary: kick your exploration up a notch at some of the top local zipline courses and adventure parks, make a splash at Noah's Ark Water Park, test your team's savvy at popular escape rooms, and get in on the family fun at Mt. Olympus Water & Theme Park.

To find where to stay, ratings, other places to visit, and other tourist information, you can read our Wisconsin Dells tour planning tool.

You can drive from Milwaukee to Wisconsin Dells in 2.5 hours. Alternatively, you can take a train; or do a combination of bus and train. Traveling from Milwaukee in August, Wisconsin Dells is little chillier at night with lows of 59°F. Finish your sightseeing early on the 19th (Fri) to allow enough time to travel back home.
Theme Parks · Tours · Fun & Games · Adventure
Side Trips

Wisconsin travel guide

Specialty Museums · Water Parks · Zoos
The Badger State
Wisconsin is known as "America's Dairyland" because of its status as the nation's most famous producer of milk and cheese. A growing favorite with foreign tourists, the state is a perfect holiday destination for nature lovers, offering year-round outdoor activities like fishing, boating, kayaking, and hiking. Dotted with thousands of inland lakes and waterways alongside apple and cherry orchards, Wisconsin also offers numerous urban tourist attractions, its cities hosting renowned beer and art festivals each year.