2 days in Illinois Itinerary

2 days in Illinois Itinerary

Created using Inspirock Illinois trip planner

Make it your trip
1
Chicago
— 1 day
Drive
2
Oregon
— 1 night
Drive

S M T W T F S
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31
1
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3

Chicago

— 1 day

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 1st (Thu), enjoy breathtaking views from Skydeck Chicago - Willis Tower, admire the masterpieces at The Art Institute of Chicago, appreciate the history behind Cloud Gate, then stroll through Millennium Park, and finally admire the striking features of 360 Chicago Observation Deck.

For other places to visit, photos, reviews, and tourist information, read our Chicago vacation builder.

Use the Route module to find suitable travel options from your home destination to Chicago. In August, daytime highs in Chicago are 83°F, while nighttime lows are 67°F. Cap off your sightseeing on the 1st (Thu) early enough to travel to Oregon.

Things to do in Chicago

Museums · Parks

Oregon

— 1 night
Oregon is a city in and the county seat of Ogle County, Illinois, United States. You've now added Lowden State Park to your itinerary. Kick off your visit on the 2nd (Fri): immerse yourself in nature at Castle Rock State Park, then admire the majestic nature at Lowden State Park, and then browse the different shops at Conover Square.

To see traveler tips, maps, and other tourist information, you can read our Oregon travel route planning site.

You can drive from Chicago to Oregon in 2 hours. Traveling from Chicago in August, expect a bit cooler with lows of 58°F in Oregon. Finish your sightseeing early on the 2nd (Fri) so you can travel back home.

Things to do in Oregon

Parks · Nature · Shopping

Illinois travel guide

4.4
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.