Discovering Illinois: A 4-Day Family Friendly Rail/Train Road Trip Itinerary

Day 1: Urban Adventures in Chicago

Chicago, Illinois

8:00AM

Breakfast at Wildberry Pancakes and Cafe

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe, known for their mouthwatering pancakes and omelettes.
Located at 130 E Randolph St, Chicago, IL 60601
$20, 1 hour

10:00AM

Art Institute of Chicago

Spend the morning exploring the Art Institute of Chicago, home to an impressive collection of art from around the world.
Head to 111 S Michigan Ave, Chicago, IL 60603
$25, 2-3 hours

1:00PM

Lunch at Portillo's

Enjoy a classic Chicago hot dog or Italian beef sandwich at Portillo's.
Visit 100 W Ontario St, Chicago, IL 60654
$15, 1 hour

3:00PM

Navy Pier

Explore Navy Pier, a popular spot for entertainment, dining, and sightseeing along Lake Michigan.
Visit 600 E Grand Ave, Chicago, IL 60611
Free, 2-3 hours

6:00PM

Dinner at Lou Malnati's Pizzeria

Indulge in a deep-dish pizza dinner at Lou Malnati's, a Chicago staple.
Head to 439 N Wells St, Chicago, IL 60654
$30, 1-2 hours
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Day 2: Historical Exploration in Springfield

Springfield, Illinois

9:00AM

Breakfast at Charlie Parker's Diner

Start your day with a hearty breakfast at Charlie Parker's Diner, a classic Route 66 eatery.
Visit 700 North St, Springfield, IL 62704
$15, 1 hour

11:00AM

Abraham Lincoln Presidential Library and Museum

Explore the life and legacy of Abraham Lincoln at the Presidential Library and Museum.
Head to 212 N 6th St, Springfield, IL 62701
$15, 2-3 hours

1:00PM

Lunch at Fulgenzi's Pizza & Pasta

Enjoy a delicious Italian lunch at Fulgenzi's, known for their pizza and pasta dishes.
Visit 1168 E Sangamon Ave, Springfield, IL 62702
$20, 1 hour

3:00PM

Lincoln Home National Historic Site

Visit the Lincoln Home National Historic Site and explore the neighborhood where Abraham Lincoln lived before becoming president.
Explore 413 S 8th St, Springfield, IL 62701
Free, 1-2 hours

6:00PM

Dinner at Obed & Isaac's Microbrewery

Enjoy a relaxing dinner at Obed & Isaac's, a historic microbrewery with a charming beer garden.
Head to 500 S 6th St, Springfield, IL 62701
$25, 1-2 hours
View Hotel Availability

Day 3: Scenic Delights in Galena

Galena, Illinois

9:00AM

Breakfast at Otto's Place

Start your day with a cozy breakfast at Otto's Place, known for their delicious breakfast dishes.
Visit 100 Bouthillier St, Galena, IL 61036
$15, 1 hour

11:00AM

Galena Heritage Trail

Embark on a leisurely walk along the Galena Heritage Trail, enjoying the scenic beauty of the area.
Trail access points throughout Galena
Free, 1-2 hours

1:00PM

Lunch at One Eleven Main

Indulge in a gourmet lunch at One Eleven Main, a popular dining spot in the heart of Galena.
Visit 111 N Main St, Galena, IL 61036
$25, 1 hour

3:00PM

Galena Cellars Vineyard & Winery

Spend the afternoon wine tasting at Galena Cellars Vineyard & Winery, sampling local wines in a picturesque setting.
Explore 4746 N Ford Rd, Galena, IL 61036
$20, 2-3 hours

6:00PM

Dinner at Fried Green Tomatoes

Enjoy a Southern-inspired dinner at Fried Green Tomatoes, known for their comfort food and hospitality.
Head to 213 N Main St, Galena, IL 61036
$30, 1-2 hours
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Day 4: Academic Exploration in Champaign-Urbana

Champaign-Urbana, Illinois

9:00AM

Breakfast at Le Peep

Start your day with a delightful breakfast at Le Peep, known for their extensive breakfast menu.
Visit 2209 S Neil St, Champaign, IL 61820
$12, 1 hour

11:00AM

University of Illinois at Urbana-Champaign

Explore the University of Illinois at Urbana-Champaign campus, known for its academic excellence and beautiful architecture.
Head to 601 E John St, Champaign, IL 61820
Free, 2-3 hours

1:00PM

Lunch at Black Dog Smoke & Ale House

Enjoy a barbecue lunch at Black Dog Smoke & Ale House, a local favorite for smoked meats and craft beers.
Visit 201 N Broadway Ave, Urbana, IL 61801
$20, 1 hour

3:00PM

Krannert Art Museum

Discover art from around the world at the Krannert Art Museum, located on the University of Illinois campus.
Explore 500 E Peabody Dr, Champaign, IL 61820
$10, 1-2 hours

6:00PM

Dinner at Big Grove Tavern

Indulge in a farm-to-table dinner at Big Grove Tavern, known for their seasonal dishes and locally sourced ingredients.
Head to 1 E Main St, Champaign, IL 61820
$30, 1-2 hours
View Hotel Availability