Ready to hit the open road? Whether you’re craving lakeside serenity, small-town charm, or breathtaking natural wonders, “Road trips from Chicago” offer a treasure trove of unforgettable escapes—all starting from the Windy City. In this guide, we’ll explore scenic routes, hidden gems, and must-see destinations that promise adventure, relaxation, and everything in between. So pack your bags, cue up your favorite playlist, and let’s roll!
1. Chicago Botanic Garden (Glencoe, IL)
Distance from Chicago: Approximately 20 miles (30-40 minutes via I-94 E)
The Chicago Botanic Garden spans 385 acres with 27 gardens and four natural areas. Highlights include the Japanese Garden, with its serene koi ponds and arched bridges, and the Rose Garden, perfect for a leisurely stroll. The garden offers tram tours for a guided overview, covering key areas with minimal walking. Seniors can enjoy the Model Railroad Garden, a whimsical display of miniature trains winding through American landmarks. The Regenstein Fruit & Vegetable Garden provides inspiration for home gardening. The garden’s Krasberg Rose Garden Café offers light meals with scenic views.
The garden is highly accessible, with paved pathways, benches, and wheelchairs available for loan. Tram tours reduce walking demands, and the flat terrain makes navigation easy. Restrooms and shaded seating areas are plentiful, ensuring comfort. The tranquil setting is ideal for relaxation, and educational programs, such as gardening workshops, cater to curious minds.
Driving Routes:
- Direct Route (I-94 E): Take I-94 E from Chicago to Dundee Road (20 miles, 30 minutes). This is the fastest route, ideal for minimizing travel time.
- Scenic Route (Sheridan Road): Exit I-94 E at Lake Cook Road and follow Sheridan Road north through Winnetka and Glencoe (25 miles, 50 minutes). This route offers views of Lake Michigan and passes through charming North Shore neighborhoods with historic mansions. Stop at the Baha’i House of Worship in Wilmette, a stunning architectural gem with accessible gardens, for a short visit.
2. Morton Arboretum (Lisle, IL)
Distance from Chicago: Approximately 25 miles (40-50 minutes via I-88 W)
The Morton Arboretum is a 1,700-acre living museum with over 4,000 tree species. Seniors can explore the East and West Sides via a 9-mile driving loop, with pull-offs at scenic spots like the Meadow Lake overlook. The Acorn Express tram offers a narrated one-hour tour, perfect for those preferring less walking. The Ginkgo Café provides accessible dining with views of the grounds. Seasonal events, like the fall color festival, showcase vibrant foliage, while the Arboretum’s library offers a quiet space to learn about horticulture.
The Arboretum is senior-friendly, with paved trails, ample benches, and mobility scooter rentals. The tram tour is ideal for those with limited mobility, and the visitor center provides clear maps and accessibility information. The calm environment and educational exhibits appeal to seniors interested in nature and conservation.
Driving Routes:
- Direct Route (I-88 W): Take I-290 W to I-88 W, exiting at IL-53 (25 miles, 40 minutes). This route is straightforward and efficient.
- Scenic Route (IL-83 S): Follow IL-83 S through Hinsdale and Darien (30 miles, 1 hour). This route passes through suburban areas with tree-lined streets and historic homes. Stop at the Graue Mill and Museum in Oak Brook (15 miles from Chicago), a restored 1852 gristmill with accessible exhibits on local history, perfect for a short break.
3. North Shore Area (Evanston, IL)
Distance from Chicago: Approximately 14 miles to downtown Evanston (25-35 minutes via Lake Shore Drive)
Evanston, part of Chicago’s North Shore, offers a blend of cultural and natural attractions. The Northwestern University campus features historic buildings and lakefront views, with accessible paths for strolling. The Grosse Point Lighthouse, a 1873 landmark, offers guided tours (note: the tower climb may not suit all seniors). Downtown Evanston’s shops and cafés, like the Colectivo Coffee on Church Street, provide a relaxed atmosphere. The Ladd Arboretum offers quiet trails and birdwatching opportunities.
Evanston is highly walkable with flat sidewalks and accessible public spaces. Many attractions, like the lighthouse grounds and university campus, have paved paths and benches. Restaurants and cafés cater to dietary needs, and the area’s low-key vibe suits seniors seeking a mix of history, culture, and relaxation.
Driving Routes:
- Direct Route (Lake Shore Drive): Take Lake Shore Drive north to Sheridan Road (14 miles, 25 minutes). This route offers stunning views of Lake Michigan and Chicago’s skyline.
- Scenic Route (N Clark St): Follow N Clark Street through Andersonville and Rogers Park (16 miles, 40 minutes). This route passes vibrant neighborhoods with historic architecture. Stop at the Leather Archives & Museum in Rogers Park (10 miles from Chicago), which offers accessible exhibits on cultural history for those interested in unique museums.
Related: Best Day Trips for Seniors in South Carolina
4. Lake Geneva, Wisconsin
Distance from Chicago: Approximately 80 miles (1.5-2 hours via US-12 W)
Lake Geneva is a charming resort town with a 26-mile shore path around Geneva Lake, offering stunning views of historic mansions and the water. Seniors can opt for shorter, accessible sections of the path near Library Park. Boat tours, like those offered by Lake Geneva Cruise Line, provide narrated history cruises with minimal physical exertion. The town’s downtown features senior-friendly shops and restaurants, such as the Grand Geneva Resort’s café. Yerkes Observatory, a historic astronomical site, offers guided tours with limited walking.
Lake Geneva is ideal for seniors, with flat, accessible paths in downtown areas and boat tours that eliminate walking needs. Many restaurants offer outdoor seating with lake views, and attractions like Yerkes Observatory provide benches and accessible facilities. The relaxed pace and scenic beauty make it a perfect getaway.
Driving Routes:
- Direct Route (US-12 W): Take I-94 W to US-12 W, exiting at WI-50 (80 miles, 1.5 hours). This route is efficient and well-maintained.
- Scenic Route (IL-47 N): Follow IL-47 N through Woodstock and Richmond (90 miles, 2 hours). This route winds through rural Illinois, with rolling farmland and small towns. Stop at the Woodstock Square Historic District (50 miles from Chicago), featuring a charming town square with accessible shops and the historic Woodstock Opera House for a cultural break.
5. Milwaukee, Wisconsin
Distance from Chicago: Approximately 92 miles (1.5-2 hours via I-94 W)
Milwaukee is a vibrant city with a rich cultural scene. The Milwaukee Art Museum, with its stunning lakefront architecture, offers accessible galleries showcasing American and European art. The Harley-Davidson Museum provides a fascinating look at motorcycle history with senior-friendly walking paths and benches. The Milwaukee Riverwalk offers a flat, scenic stroll with nearby cafés like Colectivo Coffee for a relaxing break. Lakefront Brewery tours include tastings and accessible seating, perfect for enjoying Wisconsin’s craft beer culture.
Milwaukee is highly accessible, with flat sidewalks, ample benches, and wheelchair-friendly attractions. Museums offer elevators and seating areas, and the Riverwalk’s paved paths are ideal for leisurely walks. The city’s laid-back vibe and senior-friendly dining options make it a great destination.
Driving Routes:
- Direct Route ( Interstate 94 W): Take I-94 W to Milwaukee (92 miles, 1.5 hours). This is the fastest route, ideal for minimizing travel time.
- Scenic Route (Sheridan Road): Follow Sheridan Road north through Kenosha and Racine (100 miles, 2.5 hours). This route hugs Lake Michigan, offering stunning water views and charming small towns. Stop at the Kenosha Public Museum (60 miles from Chicago), which has accessible exhibits on local history and art.
6. Starved Rock State Park (Utica, IL)
Distance from Chicago: Approximately 95 miles (1.5-2 hours via I-80 W)
Starved Rock State Park features 13 miles of trails with stunning canyons, waterfalls, and river views. The Starved Rock Lodge offers guided trolley tours, ideal for seniors, covering park highlights with minimal walking. The visitor center provides historical exhibits on the area’s Native American and pioneer past. The lodge’s restaurant serves hearty meals with scenic views, and nearby Matthiessen State Park offers additional accessible trails.
The park’s trolley tours and flat boardwalk trails, like the one to Starved Rock itself, are perfect for seniors with limited mobility. The lodge provides accessible facilities, including restrooms and dining areas. Benches and shaded spots ensure comfort, making it ideal for nature lovers seeking low-effort exploration.
Driving Routes:
- Direct Route (I-80 W): Take I-55 S to I-80 W, exiting at IL-178 (95 miles, 1.5 hours). This route is quick and straightforward.
- Scenic Route (IL-71): Follow IL-71 W through Yorkville and Ottawa (100 miles, 2 hours). This route winds through rural landscapes with farmland and small towns. Stop at the Reddick Mansion in Ottawa (80 miles from Chicago), a historic 1850s home with accessible ground-floor tours.
7. Galena, Illinois
Distance from Chicago: Approximately 165 miles (2.5-3 hours via US-20 W)
Galena is a historic town with 85% of its buildings listed on the National Register of Historic Places. Main Street features charming shops, galleries, and cafés, all accessible with flat sidewalks. The Ulysses S. Grant Home offers guided tours of the former president’s residence, with minimal walking. The Dowling House, Galena’s oldest home, provides historical insights. Trolley tours cover key sites, and the Mississippi River offers scenic boat cruises.
Galena’s compact downtown is walkable, with benches and accessible restrooms. Trolley and boat tours minimize physical exertion, and many restaurants cater to dietary needs. The town’s relaxed pace and historical charm make it a delightful destination for seniors.
Driving Routes:
- Direct Route (US-20 W): Take I-90 W to US-20 W (165 miles, 2.5 hours). This route is efficient and well-maintained.
- Scenic Route (IL-2): Follow IL-2 (Great River Road) along the Mississippi River from Rockford (170 miles, 3.5 hours). This route offers breathtaking river views and rolling hills. Stop at the Apple River Fort State Historic Site in Elizabeth (140 miles from Chicago), a reconstructed 1832 fort with accessible exhibits.
8. Amish Country (Shipshewana, IN)
Distance from Chicago: Approximately 135 miles (2.5-3 hours via I-90 E)
Shipshewana is the heart of Indiana’s Amish Country, known for its quaint charm. The Shipshewana Flea Market (seasonal, May-October) offers accessible shopping for crafts and antiques. The Menno-Hof Amish and Mennonite Museum provides wheelchair-friendly exhibits on Amish culture. Buggy rides offer a low-effort way to explore the countryside, and restaurants like the Blue Gate serve hearty, senior-friendly meals with dietary options.
The flat terrain, accessible museum, and buggy rides make Shipshewana ideal for seniors. The flea market has paved paths, and rest areas are plentiful. The peaceful, slow-paced environment is perfect for older travelers seeking cultural immersion.
Driving Routes:
- Direct Route (I-90 E): Take I-90 E (Indiana Toll Road) to IN-9 S (135 miles, 2.5 hours). This is the quickest route.
- Scenic Route (US-20 E): Follow US-20 E through South Bend (140 miles, 3 hours). This route passes rolling farmland and small towns. Stop at the Studebaker National Museum in South Bend (100 miles from Chicago), which offers accessible exhibits on automotive history.
9. Holland, Michigan
Distance from Chicago: Approximately 150 miles (2.5-3 hours via I-94 E)
Holland is known for its Dutch heritage and scenic beauty. Windmill Island Gardens features a 250-year-old working windmill and accessible gardens. The Holland Museum offers exhibits on Dutch history with wheelchair access. Nelis’ Dutch Village provides a cultural experience with shops and a petting zoo, easily navigated by seniors. During May, the Tulip Time Festival showcases vibrant flower displays. Lake Michigan’s beaches, like Holland State Park, offer accessible boardwalks.
Holland’s flat paths, benches, and accessible attractions make it senior-friendly. Museums and gardens provide low-effort exploration, and restaurants like DeBoer’s Bakery cater to varied diets. The town’s welcoming atmosphere is perfect for leisurely visits.
Driving Routes:
- Direct Route (I-94 E): Take I-94 E to US-31 N (150 miles, 2.5 hours). This route is fast and direct.
- Scenic Route (Lake Shore Drive to US-12): Follow Lake Shore Drive to US-12 E through New Buffalo and St. Joseph (160 miles, 3.5 hours). This route hugs Lake Michigan, offering coastal views. Stop at the St. Joseph Lighthouse (120 miles from Chicago), with accessible grounds for scenic photo ops.
10. Madison, Wisconsin
Distance from Chicago: Approximately 150 miles (2.5-3 hours via I-90 W)
Madison, Wisconsin’s capital, blends urban and natural attractions. The Wisconsin State Capitol offers free, accessible guided tours of its stunning architecture. Olbrich Botanical Gardens features 16 acres of accessible gardens and a tropical conservatory. The University of Wisconsin’s Arboretum provides paved trails for birdwatching. The Dane County Farmers’ Market (seasonal, Saturdays) offers local produce and crafts in a walkable setting. Lakeside cafés like Mariner’s Inn provide scenic dining.
Madison’s attractions are senior-friendly, with flat paths, elevators in the Capitol, and mobility aids at gardens. The city’s compact layout and ample seating make exploration comfortable. Its vibrant yet relaxed vibe appeals to seniors interested in culture and nature.
Driving Routes:
- Direct Route (I-90 W): Take I-90 W to Madison (150 miles, 2.5 hours). This route is efficient and well-paved.
- Scenic Route (US-14 W): Follow US-14 W through Janesville (160 miles, 3 hours). This route passes pastoral landscapes and small towns. Stop at the Lincoln-Tallman House in Janesville (110 miles from Chicago), a historic 1857 mansion with accessible ground-floor tours.
Related: Top Chicago attractions
11. Indianapolis, Indiana
Distance from Chicago: Approximately 180 miles (2.5-3 hours via I-65 S)
Indianapolis, Indiana’s capital, offers a mix of cultural and historical gems. The Indianapolis Museum of Art at Newfields features accessible galleries and a 100-acre garden with flat, paved paths for leisurely strolls. The Indiana State Museum, located in White River State Park, showcases state history with wheelchair-friendly exhibits. The Canal Walk, a 3-mile accessible pathway, offers scenic views and benches for resting. Seniors can enjoy dining at accessible restaurants like Café Patachou, known for its senior-friendly menu.
Indianapolis is highly accessible, with flat sidewalks, ample seating, and elevators in major attractions. The Canal Walk and museum grounds are ideal for those with limited mobility, and the city’s relaxed pace suits seniors seeking a blend of culture and relaxation.
Driving Routes:
- Direct Route (I-65 S): Take I-65 S from Chicago to Indianapolis (180 miles, 2.5 hours). This is the fastest, most direct route with well-maintained highways.
- Scenic Route (US-41 S): Follow US-41 S through Lowell and Lafayette (190 miles, 3.5 hours). This route offers views of Indiana’s farmland and small towns. Stop at the Frank Lloyd Wright-designed Samara House in West Lafayette (140 miles from Chicago), which offers accessible ground-floor tours of its unique architecture.
12. Springfield, Illinois
Distance from Chicago: Approximately 200 miles (3-3.5 hours via I-55 S)
Springfield, the state capital, is steeped in Abraham Lincoln history. The Abraham Lincoln Presidential Library and Museum offers accessible exhibits on the 16th president’s life, with elevators and seating. The Lincoln Home National Historic Site provides guided tours of his residence, with accessible paths in the surrounding historic neighborhood.
The Illinois State Capitol offers free, senior-friendly tours with minimal walking. The Dana-Thomas House, a Frank Lloyd Wright masterpiece, features accessible ground-floor tours. Nearby, the Route 66 Experience at the Illinois State Fairgrounds showcases nostalgic memorabilia.
Springfield’s attractions are senior-friendly, with flat terrain, benches, and accessible facilities. Many sites offer guided tours to reduce walking, and restaurants like Maldaner’s cater to dietary needs. The city’s historical focus and calm atmosphere are perfect for older travelers.
Driving Routes:
- Direct Route (I-55 S): Take I-55 S to Springfield (200 miles, 3 hours). This route is efficient and follows historic Route 66 for parts of the journey.
- Scenic Route (Old Route 66): Follow segments of historic Route 66 via IL-47 S and IL-53 S through Joliet and Bloomington (210 miles, 4 hours). This route offers nostalgic views of classic diners and small towns. Stop at the Route 66 Welcome Center in Joliet (40 miles from Chicago), which has accessible exhibits on the iconic highway’s history.
13. Michigan City, Indiana
Distance from Chicago: Approximately 60 miles (1-1.5 hours via I-94 E)
Michigan City, nestled along Lake Michigan, is known for its scenic shores and historic charm. Washington Park features an accessible beach boardwalk and the Michigan City Lighthouse, with a small museum offering historical insights. The Barker Mansion, a 1905 Gilded Age home, provides guided tours with elevator access to upper floors.
The Lubeznik Center for the Arts showcases contemporary exhibits in an accessible space. Blue Chip Casino offers low-key entertainment with senior-friendly dining options. Nearby Indiana Dunes National Park has accessible trails like the West Beach Loop.
Michigan City’s compact size and flat terrain make it ideal for seniors. Attractions offer accessible paths, benches, and restrooms, and the beach boardwalk is wheelchair-friendly. The relaxed lakeside vibe and cultural sites cater to older adults seeking a quick getaway.
Driving Routes:
- Direct Route (I-94 E): Take I-94 E to US-421 S (60 miles, 1 hour). This is the quickest route with easy highway access.
- Scenic Route (US-12 E): Follow US-12 E (Red Arrow Highway) through New Buffalo (65 miles, 1.5 hours). This route offers Lake Michigan views and passes charming coastal towns. Stop at the New Buffalo Railroad Museum (50 miles from Chicago), a small, accessible museum with exhibits on local rail history.
Conclusion
These road trips from Chicago offer seniors a chance to explore the Midwest’s natural beauty, cultural landmarks, and historic treasures in comfort. Whether you’re seeking a quick day trip to the Morton Arboretum or a weekend adventure in Door County, these destinations provide accessible and enriching experiences. Always plan ahead to ensure accessibility and comfort, and enjoy the journey at your own pace.