12 days in Chicago and Beyond Itinerary

12 days in Chicago and Beyond Itinerary

Created using Inspirock Chicago and Beyond route planner

Plan created by another user. Make it yours
Drive
1
DeKalb
— 1 night
Drive
2
Waukegan
— 2 nights
Drive
3
Chicago
— 8 nights

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1
night
DeKalb

DeKalb is a city in DeKalb County, Illinois, United States. Start off your visit on the 19th (Sat): don't miss a visit to Old Settlers Memorial Cabin and then relax in the rural setting at Edwards Apple Orchard. On the next day, steep yourself in history at Farnsworth House, take an in-depth tour of Ellwood House Museum, and then sample the fine beverages at Whiskey Acres Distilling Co..

To find photos, traveler tips, other places to visit, and tourist information, you can read our DeKalb trip itinerary planner.

Chicago to DeKalb is an approximately 1.5-hour car ride. Traveling from Chicago in September, plan for slightly colder nights in DeKalb, with lows around 54°F. Wrap up your sightseeing on the 20th (Sun) to allow time to travel to Waukegan.

Things to do in DeKalb

Museums · Shopping · Historic Sites · Breweries & Distilleries

Side Trips

2
nights
Waukegan

Waukegan is a city and the county seat of Lake County, Illinois, United States. On the 21st (Mon), go for a walk through Chicago Botanic Garden, tour the pleasant surroundings at Rosewood Beach, and then tour the pleasant surroundings at Glencoe Beach. Here are some ideas for day two: experience rural life at Elawa Farm, then kick back and relax at Illinois Beach State Park, and then tour the pleasant surroundings at Waukegan Municipal Beach.

To find more things to do, ratings, traveler tips, and tourist information, read Waukegan tour builder website.

Traveling by car from DeKalb to Waukegan takes 1.5 hours. In September, plan for daily highs up to 74°F, and evening lows to 55°F. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Chicago.

Things to do in Waukegan

Parks · Outdoors · Beaches · Nature

Side Trips

8
nights
Chicago

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Head to The Magnificent Mile and Ernest Hemingway Birthplacefor plenty of shopping. Your itinerary includes some good beach time at Ohio Street Beach and Oak Street Beach. There's still lots to do: admire the masterpieces at The Art Institute of Chicago, stroll around Millennium Park, get curious at Museum of Science and Industry, and enjoy breathtaking views from 360 Chicago Observation Deck.

To find maps, photos, and tourist information, you can read our Chicago day trip tool.

Getting from Waukegan to Chicago by car takes about 1.5 hours. Traveling from Waukegan in September, you can expect nighttime temperatures to be somewhat warmer in Chicago, with lows of 61°F. Finish up your sightseeing early on the 30th (Wed) so you can travel back home.

Things to do in Chicago

Parks · Outdoors · Beaches · Museums

Side Trip