9 days in Milwaukee, Chicago & Oshkosh Itinerary

9 days in Milwaukee, Chicago & Oshkosh Itinerary

Created using Inspirock United States holiday builder

Make it your trip
Fly
1
Milwaukee
— 2 nights
Drive
2
Chicago
— 2 nights
Drive
3
Oshkosh
— 1 night
Drive
4
Milwaukee
— 3 nights
Fly

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Milwaukee

— 2 nights

Brew City

Milwaukee boasts well-preserved historical districts with a rich European past and a strong beer-brewing tradition.
Start off your visit on the 1st (Fri): make a trip to Black Cat Alley, take an in-depth tour of Chudnow Museum of Yesteryear, then indulge your thirst for a good beer at Miller Brewery Tour, and finally wander the streets of Historic Third Ward. Get ready for a full day of sightseeing on the 2nd (Sat): pick up some local products at Waukesha Farmers' Market, then contemplate in the serene atmosphere at Holy Hill, then admire the natural beauty at Mitchell Park Horticultural Conservatory (The Domes), and finally admire the natural beauty at Boerner Botanical Gardens.

To see reviews, photos, where to stay, and other tourist information, read our Milwaukee tour itinerary planner.

Denver to Milwaukee is an approximately 4-hour flight. You can also drive; or take a train. Due to the time zone difference, you'll lose 1 hour traveling from Denver to Milwaukee. Traveling from Denver in October, expect nights in Milwaukee to be a bit warmer, around 46°F, while days are slightly colder, around 62°F. Finish up your sightseeing early on the 3rd (Sun) so you can go by car to Chicago.

Things to do in Milwaukee

Shopping · Parks · Neighborhoods · Historic Sites

Side Trips

Chicago

— 2 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 3rd (Sun): take in panoramic vistas at 360 Chicago Observation Deck, then stroll around Millennium Park, then admire the masterpieces at The Art Institute of Chicago, and finally get interesting insight from Tours. Get ready for a full day of sightseeing on the next day: observe the fascinating underwater world at Shedd Aquarium, then engage your brain at Museum of Science and Industry, then ponder the design of Buckingham Fountain, and finally take in panoramic vistas at Skydeck Chicago - Willis Tower.

To find ratings, more things to do, and other tourist information, refer to the Chicago trip itinerary builder.

Traveling by car from Milwaukee to Chicago takes 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a daytime high around 65°F in October, and nighttime lows around 49°F. Wrap up your sightseeing on the 5th (Tue) early enough to drive to Oshkosh.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Oshkosh

— 1 night
Oshkosh is a city in Winnebago County, Wisconsin, United States, located where the Fox River enters Lake Winnebago from the west. Start off your visit on the 5th (Tue): look for gifts at Wilmar Chocolates, trek along Wiowash Trail, then admire the masterpieces at Paine Art Center and Gardens, and finally tour the pleasant surroundings at Menominee Park.

To find traveler tips, photos, ratings, and tourist information, refer to the Oshkosh visit site.

Getting from Chicago to Oshkosh by car takes about 3 hours. Prepare for little chillier weather when traveling from Chicago in October: high temperatures in Oshkosh hover around 60°F and lows are around 43°F. Finish your sightseeing early on the 6th (Wed) to allow enough time to travel to Milwaukee.

Things to do in Oshkosh

Parks · Outdoors · Trails · Museums

Side Trip

Milwaukee

— 3 nights

Brew City

Change things up with these side-trips from Milwaukee: Madison (Henry Vilas Zoo & Wisconsin State Capitol). Enjoy Milwaukee some more: contemplate in the serene atmosphere at Basilica of St. Josaphat, explore the world behind art at Lynden Sculpture Garden, sample the tasty concoctions at Lakefront Brewery, and examine the collection at Harley-Davidson Museum.

To plan Milwaukee vacation without wasting time, ask Inspirock to design an itinerary.

Traveling by car from Oshkosh to Milwaukee takes 1.5 hours. You'll have a few hours on the 9th (Sat) to wrap things up before traveling home.

Things to do in Milwaukee

Museums · Parks · Zoos & Aquariums · Historic Sites

Side Trip