3 days in Midwest Itinerary

3 days in Midwest Itinerary

Created using Inspirock Midwest holiday planner

Make it your trip
1
Chicago
— 1 night
Drive
2
Sister Bay
— 1 night
Drive

S M T W T F S
10
11
12
13
14
15
16

Chicago

— 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 10th (Sun): take in the exciting artwork at Chicago Cultural Center, then enjoy breathtaking views from 360 Chicago Observation Deck, then observe the fascinating underwater world at Shedd Aquarium, and finally try your luck at Horseshoe Hammond. Keep things going the next day: admire the landmark architecture of Skydeck Chicago - Willis Tower, admire the striking features of Marquette Building, stroll around Millennium Park, then explore the world behind art at The Art Institute of Chicago, and finally get in on the family fun at Fox in a Box Chicago.

To see reviews, traveler tips, where to stay, and other tourist information, you can read our Chicago trip planning app.

Use the Route module to see travel options from your home to Chicago. In January, daily temperatures in Chicago can reach 32°F, while at night they dip to 18°F. Cap off your sightseeing on the 11th (Mon) early enough to go by car to Sister Bay.

Things to do in Chicago

Fun & Games · Parks · Museums · Zoos & Aquariums

Side Trip

Sister Bay

— 1 night
Sister Bay is a village in Door County, Wisconsin, United States. On the 12th (Tue), get engrossed in the history at Corner of the Past Museum, then take in the waterfront activity at Sister Bay Marina, and then don't miss a visit to Holy Transfiguration Chapel and Woods.

To find other places to visit and other tourist information, use the Sister Bay trip planner.

Getting from Chicago to Sister Bay by car takes about 5 hours. Other options: do a combination of train, bus, and car; or do a combination of flight and car. Prepare for a bit cooler weather when traveling from Chicago in January: high temperatures in Sister Bay hover around 24°F and lows are around 9°F. Finish your sightseeing early on the 12th (Tue) so you can drive back home.

Things to do in Sister Bay

Parks · Museums
Highlights from your trip