6 days in Illinois Itinerary

6 days in Illinois Itinerary

Created using Inspirock Illinois trip planner
Make it your trip
1
Chicago
— 1 night
Drive
2
Effingham
— 2 nights
Drive
3
Chester
— 2 nights
Drive

S M T W T F S
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Chicago — 1 night

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
You've added Grosse Point Lighthouse, Old Joliet Prison, Ernest Hemingway Birthplace, and other attractions to your itinerary. Start off your visit on the 18th (Wed): enjoy the sea views from Grosse Point Lighthouse, steep yourself in history at Ernest Hemingway Birthplace, don't miss a visit to Old Joliet Prison, then make a trip to Gemini Giant, then take in the views from Captain Swift Covered Bridge, and finally snap pictures at Red Covered Bridge.

To see more things to do, reviews, ratings, and tourist information, you can read our Chicago trip itinerary maker tool.

The Route module shows you all the different ways you can get to Chicago. In November in Chicago, expect temperatures between 50°F during the day and 35°F at night. Cap off your sightseeing on the 19th (Thu) early enough to go by car to Effingham.
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Historic Sites · Museums · Shopping
Side Trips

Effingham — 2 nights

Effingham is the largest city in, and the county seat of, Effingham County, Illinois, United States. Your list of things to see and do now includes Big Knitting Needles and Crochet Hook, World's Largest Rocking Chair, Abraham Lincoln Statue, and other attractions. There's more to do: learn about winemaking at Tuscan Hills Winery.

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

You can drive from Chicago to Effingham in 3.5 hours. Another option is to drive. In November, daily temperatures in Effingham can reach 53°F, while at night they dip to 34°F. Wrap up your sightseeing by early afternoon on the 21st (Sat) to allow enough time to drive to Chester.
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Wineries
Side Trips

Chester — 2 nights

Chester is a city in and the county seat of Randolph County, Illinois, United States, on a bluff above the Mississippi River. Your day by day itinerary now includes Eversgerd’s Civil War Fort, Rim Rock Recreation Trail and Kaskaskia Bell. Start off your visit on the 22nd (Sun): take in the views from Little Mary's River Covered Bridge, then steep yourself in history at Kaskaskia Bell, then contemplate the long history of Eversgerd’s Civil War Fort, and finally identify plant and animal life at Rim Rock Recreation Trail.

To find photos, ratings, other places to visit, and more tourist information, read our Chester trip planner.

Drive from Effingham to Chester in 2.5 hours. Alternatively, you can drive. November in Chester sees daily highs of 54°F and lows of 36°F at night. You'll set off for home on the 23rd (Mon).
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Historic Sites · Parks · Wildlife
Side Trips

Illinois travel guide

4.3
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.
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