43 days in Chicago and Beyond Itinerary

43 days in Chicago and Beyond Itinerary

Make it your trip
+2
Drive to Leeds Bradford Airport, Fly to Chicago O'Hare International Airport, Drive to Waukegan
1
Waukegan
— 3 nights
Drive
2
Rockford
— 6 nights
Drive
3
Ottawa
— 2 nights
Drive
4
Kankakee
— 2 nights
Drive
5
Chicago
— 29 nights
Fly to London Heathrow, Train to York

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Waukegan — 3 nights

Waukegan is a city and the county seat of Lake County, Illinois, United States. You'll find plenty of places to visit near Waukegan: Three Oaks Recreation Area (in Crystal Lake) and Volo Bog State Natural Area (in Ingleside). Next up on the itinerary: stroll around Independence Grove Forest Preserve, enjoy the sand and surf at Rosewood Beach, indulge your thirst for a good beer at ZumBier, and delve into the lush surroundings at Fort Sheridan Forest Preserve.

To find maps, where to stay, traveler tips, and more tourist information, you can read our Waukegan holiday planner.

York, UK to Waukegan is an approximately 17-hour combination of car and flight. You'll gain 6 hours traveling from York to Waukegan due to the time zone difference. Expect somewhat warmer temperatures when traveling from York in July; daily highs in Waukegan reach 30°C and lows reach 18°C. Wrap up your sightseeing on the 13th (Tue) to allow time to drive to Rockford.
Parks · Wildlife · Outdoors · Nature
Side Trips

Rockford — 6 nights

Rockford is the third largest city in the U.S. state of Illinois, the 171st most populous city in the United States, the largest city in Illinois outside of the Chicago metropolitan area, and the city of the 148th most populous metropolitan area in the United States. Historical Auto Attractions and Frank Lloyd Wright's Laurent House are good opportunities to explore the local culture. Let the collections at Discovery Center Museum and Northwest Territory Historic Center capture your imagination. Venture out of the city with trips to Whiskey Acres Distilling Co. (in DeKalb), Dixon (Loveland Community House, Veterans Memorial Park, &more) and Freeport (Oscar Taylor Home, Oakdale Nature Preserve, &more). There's still lots to do: stroll through Kishwaukee River Forest Preserve, cool off at Magic Waters Waterpark, see the interesting displays at The Eagle's Nest Art Colony Collection, and admire the natural beauty at Anderson Japanese Gardens.

For ratings, photos, more things to do, and other tourist information, use the Rockford trip itinerary builder site.

You can drive from Waukegan to Rockford in 2 hours. In July in Rockford, expect temperatures between 33°C during the day and 20°C at night. Finish your sightseeing early on the 19th (Mon) so you can drive to Ottawa.
Museums · Parks · Wildlife · Wineries
Side Trips

Ottawa — 2 nights

Ottawa is a city located at the confluence of the navigable Illinois River and Fox River in LaSalle County, Illinois, United States. Kick off your visit on the 20th (Tue): admire the majestic nature at Starved Rock State Park, learn about winemaking at August Hill Winery & Illinois Sparkling Co. Tasting Room, then immerse yourself in nature at Matthiessen State Park, and finally stroll around Washington Square Park. Keep things going the next day: relax and rejuvenate at SaltTreeYoga, then see the interesting displays at Reddick Mansion and Gardens, and then do a tasting at Fox Valley Winery.

For maps, where to stay, ratings, and more tourist information, refer to the Ottawa trip itinerary builder tool.

Traveling by car from Rockford to Ottawa takes 1.5 hours. In July, plan for daily highs up to 32°C, and evening lows to 20°C. Finish your sightseeing early on the 21st (Wed) so you can travel to Kankakee.
Parks · Nature · Wineries · Museums
Side Trips

Kankakee — 2 nights

Kankakee is a city in and the county seat of Kankakee County, Illinois, United States. Start off your visit on the 22nd (Thu): immerse yourself in nature at Kankakee River State Park, tour the pleasant surroundings at Midewin National Tallgrass Prairie, and then see the interesting displays at Exploration Station...a children's museum. Get ready for a full day of sightseeing on the 23rd (Fri): look and learn at Strickler Planetarium and then cast your line with Big River Fly Fishing.

Make your Kankakee itinerary with Inspirock to find out what to see and where to go.

Drive from Ottawa to Kankakee in 1.5 hours. July in Kankakee sees daily highs of 32°C and lows of 19°C at night. Finish up your sightseeing early on the 23rd (Fri) so you can go by car to Chicago.
Wildlife · Parks · Museums · Outdoors
Side Trips

Chicago — 29 nights

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
The Art Institute of Chicago and Museum of Science and Industry are good opportunities to explore the local culture. Field Museum and First Division Museum at Cantigny will appeal to museum buffs. Explore the numerous day-trip ideas around Chicago: Spring Valley (in Schaumburg), Lynfred Winery (in Roselle) and Busse Woods Trail System (in Elk Grove Village). There's still lots to do: take a stroll through The Magnificent Mile, admire nature's wide array of creatures at Shedd Aquarium, head outdoors with Outdoor Activities, and stop by Wicker Park.

To see ratings, maps, photos, and tourist information, use the Chicago road trip planning tool.

Traveling by car from Kankakee to Chicago takes 1.5 hours. In July, plan for daily highs up to 33°C, and evening lows to 22°C. Finish up your sightseeing early on the 21st (Sat) so you can travel back home.
Parks · Museums · Outdoors · Neighborhoods
Side Trips