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Adventure

Route 66 Adventure

scenic drive historic summer
Length
7 days
Stops
9
Destination
Dates
Guests 1 room, 1 adults, 0 children
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What this plan covers

Embark on a classic American road trip along the historic Route 66. This scenic drive takes you through iconic landmarks, quirky roadside attractions, and stunning landscapes.

Landmark 3 Activity 3 Scenic 1 Nature 1 Stop 1

Opening hours, prices and routes can change, so check the details before you set off.

Day 1 1 stop · about 1 hrs
1

Willis Tower

Landmark 1-2 hours

The Willis Tower (formerly Sears Tower) is an iconic skyscraper offering breathtaking views of Chicago from its observation deck. It's a must-visit for first-time visitors.

Good to know

Entry fee for the Skydeck is around $30; book tickets in advance to avoid long lines. The best time to visit is during the late afternoon.

Day 2 2 stops · about 2 hrs
2

Route 66 Museum

Activity 1-2 hours

This museum showcases the history and culture of Route 66, featuring vintage cars and memorabilia. It's a fun stop to learn about the famous highway's legacy.

Good to know

Free entry; the museum is open daily. Consider visiting on weekends for special events.

3

Meramec Caverns

Activity 1-2 hours

These stunning caverns are rich in history and geological features. Guided tours reveal stunning formations and the stories behind them.

Good to know

Entry fee is around $20; tours run frequently. Booking ahead is suggested during summer.

Day 3 1 stop · about 2 hrs
4

Ozarks Scenic Byway

Scenic 2-3 hours

This route takes you through the beautiful Ozark Mountains, offering stunning views of the landscape. Stop for photos and enjoy the natural beauty.

Good to know

Free to drive; best enjoyed during daylight hours. Be cautious of wildlife on the roads.

Day 4 1 stop · about 1 hrs
5

Cadillac Ranch

Landmark 1-2 hours

Cadillac Ranch is an iconic public art installation featuring half-buried Cadillac cars. It’s a quirky stop perfect for fun photos.

Good to know

Free entry; bring spray paint to add your own touch to the cars! Open year-round.

Day 5 1 stop · about 2 hrs
6

Petrified Forest National Park

Nature 2-3 hours

This unique park features stunning petrified wood and incredible badlands. It's an otherworldly landscape worth exploring.

Good to know

Entry fee is around $20; the park is open year-round. Arrive early for the best experience.

Day 6 1 stop · about 1 hrs
7

Route 66 Car Museum

Activity 1-2 hours

This museum showcases classic cars and memorabilia from Route 66. It's a nostalgic stop for car enthusiasts and history buffs.

Good to know

Small entry fee; check for special exhibitions. Open during summer months.

Day 7 2 stops · about 3 hrs
8

Santa Monica Pier

Landmark 1-2 hours

The Santa Monica Pier is a classic California landmark featuring an amusement park, restaurants, and beautiful ocean views. A perfect way to conclude your road trip.

Good to know

Free to visit; parking is available but can be expensive. Best time to visit is during the late afternoon.

9

Venice Beach

Stop 2-3 hours

Venice Beach is vibrant and eclectic, known for its boardwalk, street performers, and unique culture. Enjoy people-watching and the beach atmosphere.

Good to know

Free access to the beach; parking can be challenging. Consider using public transport to avoid parking issues.

Where to stay

Hotels in Chicago

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Things to book

Tours and activities in Chicago

Guided tours, day trips and tickets to book alongside your stay.

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More Chicago itineraries

Other ways to spend a few days in Chicago, from our own travel research.

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