22 days in Indiana & Illinois Itinerary

Created using Inspirock United States tour itinerary planner
Make it your trip
— 2 nights
Oak Park
— 3 nights
— 4 nights
— 3 nights
— 3 nights
— 6 nights


Hammond — 2 nights

Hammond is a city in Lake County, Indiana, United States. Get some historical perspective at Basilica of the Sacred Heart and Grotto of Our Lady Lourdes. Visiting Oak Savannah Trail and Indiana Dunes State Park will get you outdoors. You'll find plenty of places to visit near Hammond: Butler Winery (in Chesterton) and Century of Progress Architectural District (in Beverly Shores). Next up on the itinerary: try to win big at Horseshoe Hammond.

To see ratings, traveler tips, more things to do, and more tourist information, read our Hammond trip maker app.

London, UK to Hammond is an approximately 11.5-hour flight. You'll gain 6 hours traveling from London to Hammond due to the time zone difference. Plan for somewhat warmer temperatures traveling from London in June, with highs in Hammond at 30°C and lows at 17°C. Cap off your sightseeing on the 7th (Wed) early enough to go by car to Oak Park.
Parks · Historic Sites · Nature · Trails
Side Trips

Oak Park — 3 nights

Oak Park is a village adjacent to the West Side of the city of Chicago in Cook County, Illinois, United States. Let the collections at Ernest Hemingway Birthplace and Berwyn Route 66 Museum capture your imagination. Your inner history buff will appreciate Frank Lloyd Wright's Unity Temple and Baha'i House of Worship. And it doesn't end there: admire the striking features of Frank Lloyd Wright Home and Studio, take in the architecture and atmosphere at St. Edmund Parish, stroll through Centennial Bike Trail, and contemplate the long history of Pleasant Home.

For reviews, ratings, where to stay, and more tourist information, read Oak Park trip maker app.

Traveling by car from Hammond to Oak Park takes an hour. Alternatively, you can drive. In June, plan for daily highs up to 32°C, and evening lows to 20°C. Finish up your sightseeing early on the 10th (Sat) so you can go by car to Naperville.
Historic Sites · Trails · Outdoors · Parks
Side Trips

Naperville — 4 nights

Naperville is a city in DuPage and Will counties in the U.S. state of Illinois, and a suburb of Chicago. Get some cultural insight at Cantigny Park and Historic Auto Attractions. Museum-lovers will get to explore Friends of the Viking Ship and Pioneer Sholes Historic Site. Explore Naperville's surroundings by going to Abraham Lincoln National Cemetery (in Elwood), St. Joseph Catholic Church (in Joliet) and Whiskey Acres Distilling Co. (in DeKalb). Next up on the itinerary: admire the natural beauty at Weber House and Garden, immerse yourself in nature at Starved Rock State Park, appreciate the extensive heritage of Riverwalk Lot, and explore the landscape on two wheels at Illinois Prairie Path.

To find ratings, more things to do, reviews, and more tourist information, refer to the Naperville itinerary planning app.

Getting from Oak Park to Naperville by car takes about an hour. Other options: drive. In June, daily temperatures in Naperville can reach 32°C, while at night they dip to 18°C. Wrap up your sightseeing on the 14th (Wed) early enough to travel to Makanda.
Historic Sites · Parks · Museums · Trails
Side Trips

Makanda — 3 nights

Makanda is a village in Jackson County, Illinois, United States. Get outdoors at Shawnee Bluffs Canopy Tour and Shawnee Hills. Do some cultural sightseeing at Mound City National Cemetery and Blue Sky Vineyard. Explore the numerous day-trip ideas around Makanda: Henry N Barkhausen Cache River Wetlands Center (in Cypress) and Mermet Springs Scuba (in Vienna). There's still lots to do: hike along Pomona Natural Bridge, appreciate the history behind Bald Knob Cross of Peace, and do a tasting at Alto Vineyards.

To find where to stay, reviews, maps, and tourist information, read our Makanda trip itinerary tool.

Use the Route module to find suitable travel options from Naperville to Makanda. Expect somewhat warmer evenings in Makanda when traveling from Naperville in June, with lows around 22°C. Finish your sightseeing early on the 17th (Sat) to allow enough time to drive to Springfield.
Outdoors · Parks · Wildlife · Trails
Side Trips

Springfield — 3 nights

Flower City

Springfield is the capital of Illinois, but its real significance is as the hometown of Abraham Lincoln.
Your cultural itinerary includes sights like Lincoln Home National Historic Site and Abraham Lincoln Presidential Library and Museum. Popular historic sites such as Dana-Thomas House and Cathedral of the Immaculate Conception are in your itinerary. Step out of Springfield to go to Petersburg and see Lincolns New Salem State Park, which is approximately 34 minutes away. Next up on the itinerary: identify plant and animal life at Lincoln Memorial Garden, walk around Union Square Park, get engrossed in the history at The Lincoln Home Visitor Center, and snap pictures at Sugar Creek Covered Bridge.

To see ratings, other places to visit, photos, and tourist information, go to the Springfield trip planner.

You can drive from Makanda to Springfield in 3.5 hours. Expect a daytime high around 34°C in June, and nighttime lows around 21°C. Wrap up your sightseeing on the 20th (Tue) to allow time to fly to Chicago.
Historic Sites · Museums · Parks · Wildlife
Side Trips

Chicago — 6 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Your cultural itinerary includes sights like The Art Institute of Chicago and Museum of Science and Industry. You'll explore and learn at Field Museum and Oriental Institute Museum. Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, appreciate the extensive heritage of Chicago Riverwalk, admire the local landmark of Buckingham Fountain, and explore the landscape on two wheels at Lakefront Trail.

To find other places to visit, where to stay, traveler tips, and more tourist information, go to the Chicago trip website.

Fly from Springfield to Chicago in 2.5 hours. Alternatively, you can drive; or take a train. In June, daytime highs in Chicago are 32°C, while nighttime lows are 20°C. Finish your sightseeing early on the 26th (Mon) so you can fly back home.
Museums · Childrens Museums · Parks · Historic Sites

Indiana travel guide

Casinos · Room Escape Games · Specialty Museums
The Hoosier State
With an extensive history of motorsports, Indiana's main claim to fame is the popular automobile race held each year in its capital city. A mostly rural state, Indiana is a land of till plains and lakes, its appearance a result of traces left behind by receding glaciers. The central section of the state, mostly flat with some rolling hills, contains some of the country's most fertile farmland. The state also contains almost 39,000 km (24,000 mi) of waterways, including the Wabash River, the longest free-flowing river east of the Mississippi. For a genuine "Hoosier" experience, tour the state's slow-paced small towns, noted for their hospitality and outstanding local cuisine. You'll remember the warmth and charm long after your vacation is over.

Illinois travel guide

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.