43 days in Chicago and Beyond, Denver & Seattle Itinerary

43 days in Chicago and Beyond, Denver & Seattle Itinerary

Created using Inspirock United States tour itinerary planner

Make it your trip
Fly to Chicago O'Hare International Airport, Drive to Waukegan
1
Waukegan
— 1 night
Drive
2
Rockford
— 5 nights
Drive
3
Ottawa
— 1 night
Drive
4
Kankakee
— 2 nights
Drive
5
Chicago
— 7 nights
Fly
6
Denver
— 11 nights
Fly
7
Seattle
— 15 nights

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Waukegan

— 1 night
Waukegan is a city and the county seat of Lake County, Illinois, United States. Kick off your visit on the 5th (Wed): identify plant and animal life at Prairie Wolf Slough and then catch the contagious excitement of Arlington Park. Keep things going the next day: cast your line with WindyCitySalmon, then go for a walk through Chicago Botanic Garden, and then contemplate in the serene atmosphere at Baha'i House of Worship.

To find other places to visit, reviews, ratings, and more tourist information, refer to the Waukegan trip itinerary maker tool.

Seattle to Waukegan is an approximately 6.5-hour combination of flight and car. You can also drive. The time zone difference when traveling from Seattle to Waukegan is 2 hours. Traveling from Seattle in May, you can expect nighttime temperatures to be a bit cooler in Waukegan, with lows of 46°F. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Rockford.

Things to do in Waukegan

Parks · Wildlife · Historic Sites · Casinos

Side Trips

Rockford

— 5 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. Explore the numerous day-trip ideas around Rockford: Dixon (The Next Picture Show, Dixon's Railroad Street Arches, &more), Whiskey Acres Distilling Co. (in DeKalb) and The Eagle's Nest Art Colony Collection (in Oregon). And it doesn't end there: take in nature's colorful creations at Anderson Japanese Gardens, trek along Stone Bridge Trail, get a new perspective on nature at Burpee Museum of Natural History, and contemplate the long history of Oscar Taylor Home.

To see ratings, where to stay, photos, and other tourist information, use the Rockford travel route planner.

Getting from Waukegan to Rockford by car takes about 2 hours. Traveling from Waukegan in May, you will find days in Rockford are a bit warmer (72°F), and nights are about the same (50°F). Wrap up your sightseeing on the 11th (Tue) to allow time to drive to Ottawa.

Things to do in Rockford

Parks · Museums · Wildlife · Trails

Side Trips

Ottawa

— 1 night
Ottawa is a city located at the confluence of the navigable Illinois River and Fox River in LaSalle County, Illinois, United States. Start off your visit on the 12th (Wed): immerse yourself in nature at Matthiessen State Park, then get engrossed in the history at Hegeler Carus Mansion, then stroll around Washington Square Park, and finally get reinvigorated at SaltTreeYoga.

Find out how to plan Ottawa trip without stress by asking Inspirock to help create an itinerary.

You can drive from Rockford to Ottawa in 1.5 hours. In May, plan for daily highs up to 72°F, and evening lows to 52°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to travel to Kankakee.

Things to do in Ottawa

Parks · Museums · Nature · Spas

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 13th (Thu): make a trip to Gemini Giant and then see what you can catch with Big River Fly Fishing. Keep things going the next day: admire the majestic nature at Kankakee River State Park, admire the striking features of B. Harley Bradley House, then examine the collection at Kankakee County Museum, and finally see the interesting displays at Kankakee Railroad Museum.

To find photos, where to stay, more things to do, and tourist information, go to the Kankakee itinerary planning tool.

You can drive from Ottawa to Kankakee in 1.5 hours. In May in Kankakee, expect temperatures between 72°F during the day and 50°F at night. Finish your sightseeing early on the 14th (Fri) to allow enough time to drive to Chicago.

Things to do in Kankakee

Wildlife · Tours · Outdoors · Museums

Side Trips

Chicago

— 7 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, enjoy breathtaking views from Skydeck Chicago - Willis Tower, get a new perspective on nature at Field Museum, and don't miss a visit to Millennium Park.

To find photos, other places to visit, and tourist information, read our Chicago day trip planning tool.

You can drive from Kankakee to Chicago in 1.5 hours. In May in Chicago, expect temperatures between 71°F during the day and 52°F at night. Finish your sightseeing early on the 21st (Fri) so you can fly to Denver.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Side Trip

Denver

— 11 nights

Mile-High City

Aptly nicknamed the "Mile-High City," Denver sits at an altitude of 1,600 m (5,280 ft) above sea level, located right where the Great Plains give way to the Rocky Mountains.
Venture out of the city with trips to Cascade (Pikes Peak - America's Mountain & North Pole Colorado Santa’s Workshop), Mini Incline (in Castle Rock) and Colorado Springs (U.S. Olympic & Paralympic Museum, Penrose Heritage Museum, &more). There's still lots to do: see the interesting displays at Colorado Model Railroad Museum, relax and rejuvenate at Healing Waters Mind and Body Float Studio, learn the secrets of beer at a beer tour and tasting, and admire the natural beauty at Benson Park Sculpture Garden.

To find ratings, traveler tips, and more tourist information, go to the Denver journey maker tool.

Traveling by flight from Chicago to Denver takes 4.5 hours. Alternatively, you can drive; or take a train. Due to the time zone difference, you'll gain 1 hour traveling from Chicago to Denver. In May, Denver is slightly colder than Chicago - with highs of 66°F and lows of 43°F. Cap off your sightseeing on the 1st (Tue) early enough to catch the flight to Seattle.

Things to do in Denver

Parks · Museums · Outdoors · Breweries & Distilleries

Side Trips

Seattle

— 15 nights

Emerald City

Nicknamed the "Emerald City" because of its abundant evergreen trees, Seattle is the cultural and business center of the Pacific Northwest, as well as a popular holiday destination.
Explore the numerous day-trip ideas around Seattle: Tacoma (Union Station & Washington State History Museum), Schack Art Center (in Everett) and Boeing Future of Flight (in Mukilteo). Dedicate the 7th (Mon) to wine at some of the top wineries in the area. There's lots more to do: shop like a local with Chihuly Garden and Glass, wander the streets of Pike Place Market, admire the sheer force of Murhut Falls, and enjoy breathtaking views from Space Needle.

To find photos, more things to do, and tourist information, you can read our Seattle trip planner.

Getting from Denver to Seattle by flight takes about 4 hours. Other options: drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Denver to Seattle. Expect slightly colder weather when traveling from Denver in June: highs in Seattle hover around 74°F, while lows dip to 57°F. Finish up your sightseeing early on the 16th (Wed) so you can travel back home.

Things to do in Seattle

Parks · Museums · Tours · Outdoors

Side Trips