4-Day Scenic Midwest Road Trip: Chicago to St. Louis

Day 1: Explore Chicago

Chicago, Illinois, USA on May 24, 2025

7:30am

Breakfast at Wildberry Pancakes and Cafe

Start the day with a delicious breakfast featuring pancakes and fresh coffee in downtown Chicago, known for its friendly atmosphere and hearty portions. Opens at 7am.
USD20, 1h

8:45am

Visit Millennium Park

Explore the iconic Cloud Gate sculpture and beautiful gardens in this famous park, perfect for photos and a leisurely walk. Open daily from 6am to 11pm.
Free, 1h

10:00am

Art Institute of Chicago

Visit one of the oldest and largest art museums in the U.S., home to Impressionist masterpieces and modern art installations. Open 10am to 5pm on Saturdays.
USD30, 2h

12:30pm

Lunch at Giordano's

Experience Chicago-style deep dish pizza at this popular local restaurant, open for lunch from 11am to 10pm.
USD25, 1h

1:45pm

Architecture River Cruise

Take a 90-minute guided boat tour along the Chicago River to learn about the city's famed architecture and history. Cruises run from 12pm to 5pm during summer.
USD45, 1h30m

4:00pm

Walk along Navy Pier

Enjoy views of Lake Michigan and explore shops, gardens, and the iconic Ferris wheel. Navy Pier is open until 10pm.
Free entry, ride tickets extra, 1h

6:00pm

Dinner at Lou Malnati’s Pizzeria

Delight in another Chicago deep dish pizza at this renowned chain famous for its buttery crust and fresh ingredients, open until 11pm.
USD30, 1h
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Day 2: History & Culture

Springfield, Illinois, USA on May 25, 2025

7:30am

Breakfast at Obed & Isaac's Microbrewery and Eatery

Kick off the day with locally sourced breakfast fare and coffee at this cozy spot. Opens at 7:30am.
USD15, 1h

9:00am

Abraham Lincoln Presidential Library & Museum

Explore engaging exhibits chronicling Lincoln's life and legacy including artifacts and interactive displays. Open 9am to 5pm.
USD17, 2h

11:30am

Lincoln Home National Historic Site

Tour the preserved home of Abraham Lincoln, providing insight into his early family life. Guided tours are hourly between 11am - 4:30pm.
Free, 1h

12:45pm

Lunch at Maldaner's Restaurant

Enjoy upscale American cuisine inspired by classic recipes, open for lunch until 2:30pm.
USD30, 1h

2:00pm

Illinois State Capitol Tour

Visit the beautiful Capitol building with a free guided tour focusing on Illinois government history. Tours available on weekdays, Saturdays check ahead.
Free, 1h

3:30pm

Route 66 Drive-In Theater Experience

Take a nostalgic drive past the famous Route 66 landmarks around Springfield—perfect for a scenic afternoon drive.
Free, 1h

6:00pm

Dinner at Cozy Dog Drive In

Try the original corn dog on a stick at this iconic Route 66 eatery, popular for casual dinner. Open until 9pm.
USD12, 1h
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Day 3: Nature & Small Town Charm

Collinsville & Alton, Illinois, USA on May 26, 2025

8:00am

Breakfast at Main Street Coffee Company

Fuel up with premium coffee and fresh pastries at this popular Collinsville café, opens at 7am.
USD10, 45m

9:00am

Cahokia Mounds State Historic Site

Explore North America’s largest pre-Columbian archaeological site featuring ancient earthworks and a museum. Open 9am to 5pm.
USD5, 2h

11:30am

Drive to Alton and Walk Historic Downtown

Stroll through Alton’s charming downtown area filled with boutiques, galleries, and historic buildings.
Free, 1h

12:30pm

Lunch at The Eagle’s Nest Restaurant

Dine with scenic river views featuring southern-inspired dishes. Lunch served from 11am to 3pm.
USD25, 1h

2:00pm

Mississippi River Overlook & Piasa Bird Trail

Take a gentle hike along the scenic Piasa Bird Trail with stunning views of the Mississippi River bluffs.
Free, 1h30m

5:00pm

Return to Collinsville for Downtown Exploration

Explore historic Main Street with shops and a casual evening vibe.
Free, 1h

6:30pm

Dinner at Horse Collar Brewing Company

Relax and enjoy craft beers and pub favorites in a friendly setting. Open until 9pm.
USD20, 1h
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Day 4: Iconic St. Louis

St. Louis, Missouri, USA on May 27, 2025

7:30am

Breakfast at Rooster

Enjoy locally sourced, creative breakfast dishes in downtown St. Louis, open from 7am.
USD18, 1h

9:00am

Visit Gateway Arch National Park

Experience the iconic Gateway Arch, including tram rides to the top for incredible city views. Park open 9am to 6pm.
USD13, 2h

11:30am

St. Louis Art Museum

Explore a vast collection of art with free general admission, including ancient to contemporary works. Open 10am to 5pm.
Free, 1h30m

1:15pm

Lunch at Pappy’s Smokehouse

Savor award-winning Memphis-style barbecue in a casual setting. Open for lunch from 11am to 3pm.
USD20, 1h

2:30pm

Forest Park Exploration

Visit one of the largest urban parks in the U.S., featuring walking trails, lakes, and cultural institutions.
Free, 2h

5:00pm

Dinner at Tony’s

Enjoy upscale Italian cuisine in this elegant downtown restaurant, perfect for a farewell dinner. Open until 10pm.
USD45, 1h30m
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