Route 66 Itinerary

Discover Route 66 in Joliet, Illinois with itineraries designed for every traveler—families, foodies, walk-and-explore travelers, and weekend adventurers. From walkable downtown sights to great places to eat and stay, Joliet delivers an unforgettable Route 66 experience.

Itinerary 1:

Family

Perfect for travelers of all ages, this itinerary features family-friendly Route 66 stops, interactive attractions, and easy-going experiences that make exploring Joliet fun for kids and adults alike.

8:00am

Breakfast at Jitters

Fuel up with a casual breakfast and coffee at a local favorite before a full day of family fun.

9:00am

Joliet Public Library

Enjoy a relaxed morning stop with kid-friendly spaces and a welcoming atmosphere for all ages.

10:30am

Haunted Trails

Arcade games, mini golf, and lunch options make this a fun, high-energy stop for the whole family.

1:00pm

Rich & Creamy

Cool down with classic ice cream flavors from one of Joliet’s most beloved dessert spots.

1:30pm

Route 66 Park

Stretch your legs and snap photos at this iconic Route 66 landmark celebrating Joliet’s road-trip legacy.

3:30pm

Joliet Area Historical Museum

Discover Joliet’s history and Route 66 stories through engaging, family-friendly exhibits.

5:30pm

Joliet Slammers Game

Wrap up the day with affordable, family-friendly baseball and classic ballpark fun.

Itinerary 2:

Overnight: Day 1

Turn your Route 66 visit into a relaxing getaway with an itinerary built around comfortable overnight stays, nearby attractions, and dining options—ideal for slowing down and soaking in Joliet.

8:00am

Social Butterfly Coffee

Start the day with handcrafted coffee and breakfast at downtown’s newest café.

9:00am

Old Joliet Prison

Explore one of Joliet’s most famous landmarks and experience its powerful history firsthand.

11:00am

Joliet Iron Works Park

Walk scenic paths through historic ruins that highlight Joliet’s industrial past.

12:00pm

Chicago Street

Stroll Joliet’s downtown corridor filled with shops, dining, and Route 66 charm.

2:00pm

Audiophil’s

Browse records and vintage finds at this unique music-focused shop.

2:30pm

Rialto Square Theatre

Admire one of Illinois’ most beautiful theaters, known for its architecture and live performances.

3:30pm

Rock & Roll Museum

Discover Joliet’s deep connection to legendary artists and music history.

5:00pm

Juliet’s Tavern

Enjoy a relaxed dinner with bold flavors in a welcoming local setting.

7:00pm

Harrah’s Casino

Unwind with drinks, gaming, entertainment, and a convenient overnight stay.

Itinerary 2:

Overnight: Day 2

Turn your Route 66 visit into a relaxing getaway with an itinerary built around comfortable overnight stays, nearby attractions, and dining options—ideal for slowing down and soaking in Joliet.

8:00am

Harrah’s Casino

(Breakfast)
Ease into the morning with breakfast before continuing your Joliet adventure.

9:00am

Planinsek Grocery & Meat Market Museum

Sitting just blocks off of Route 66, provides visitors with a nostalgic look into the past.

10:00am

Broadway Greenway

Take a peaceful walk along this scenic route connecting downtown and nearby neighborhoods.

11:00am

Rich & Creamy

Enjoy one last sweet stop before lunch and sightseeing.

12:00pm

Jacob Henry Mansion Estate

The largest & best example of Renaissance Revival architecture standing in the state of Illinois

2:00pm

Departure

Head home with lasting Route 66 memories and a deeper connection to Joliet.

Itinerary 3:

Park & Walk

Explore Route 66 at your own pace with a walkable Joliet itinerary highlighting parks, historic sites, public art, and outdoor spaces perfect for stretching your legs and taking in the scenery.

8:00am

GiGi's Sweets

(Inside Joliet Transportation Center Train Station)
Train Station)
Begin your walk with coffee and pastries inside Joliet’s historic train station.

9:00am

Joliet Railroad Museum

Explore exhibits that highlight Joliet’s role as a major transportation hub.

10:00am

Prison City Vinatge

Browse vintage clothing and unique finds in a charming downtown shop.

11:00am

Wayward Arthaus

Discover local art, creative goods, and a welcoming community space.

11:30am

Black Cat Curiosities

Step into a quirky shop filled with antiques, oddities, and conversation pieces.

12:30pm

Azul Celeste

Enjoy a flavorful lunch stop in the heart of downtown Joliet.

1:30pm

Joliet Area Historical Museum

Dive deeper into Joliet’s history with exhibits focused on Route 66 and local culture.

3:00pm

Illinois Rock & Roll Museum

Continue your walk with a music-filled stop celebrating iconic artists.

5:00pm

Yura Nuna

Savor a unique dinner experience highlighting bold, global flavors.

7:00pm

The Forge

End the day with live music or entertainment at a popular downtown venue.

Itinerary 4:

Foodie Highlights

Taste your way through Route 66 in Joliet with stops at local favorites and iconic eateries, showcasing the flavors and traditions that make the city a must-stop for food lovers.

Social Butterfly Coffee

A go-to stop for craft coffee and cozy vibes in downtown Joliet.

Richardson’s

An iconic Route 66 diner serving classic comfort food with decades of history.

Cut 158 Chophouse

A modern steakhouse offering elevated dining and bold flavors.

Rich & Creamy

A must-visit for handmade ice cream and nostalgic treats.

Milano Bakery

Finish your foodie tour with fresh-baked breads and pastries from a longtime local favorite.