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Join us at Mile 1 of Route 66 in Chicago, Illinois! 🇺🇸 In this kickoff to our epic cross-country RV road trip, we explore some of Chicago’s most iconic Route 66 landmarks, walk the legendary streets of downtown, and sample some of the best deep dish pizza the city has to offer. From the historic Palmer House Hotel to the towering Sears Tower (never Willis!), and a stop at the original Pizzeria Due, this is a deep dive into the Windy City before heading west to Santa Monica.
💨 It’s windy, it’s delicious, and it’s full of American history. Strap in for the beginning of a 2,500-mile journey on the Main Street of America.
📍 Highlights in this episode:
🚙 Start of Route 66 at Adams & Michigan
🍕 Deep dish pizza at Pequod’s & Pizzeria Due
🏨 Inside the iconic Palmer House Hotel
🚇 Walking the Loop & riding the Big Bus tour
🌆 Union Station, Chicago Riverwalk & epic skyline views
🌷 Spring tulips in bloom across the city
📅 Filmed in April 2025
🎥 Subscribe and follow along as we drive historic Route 66 all the way to California!
💰Value for value:
• Patreon: https://patreon.com/travelingrobert
• Membership: https://www.youtube.com/channel/UCLM5XNynW9u1_usGYL98YKw/join
Members and patrons get live updates from the road, early access, and bonus footage among other perks.
🌎Website:
https://travelingrobert.com
Camping Essentials: https://www.amazon.com/shop/travelingrobert/list/3V5YU1ZCB15BQ?ref_=aipsflist
Production Gear: https://www.amazon.com/shop/travelingrobert/list/3B9XKCVCHJYVZ?ref_=aipsflist
Solar and Lithium: https://www.amazon.com/shop/travelingrobert/list/3TVQ5PNPVIAD4?ref_=aipsflist
Watch our solar and lithium install video: https://youtu.be/QhJ3dcLVLyY
SOK batteries: https://www.us.sokbattery.com/?ref=lezvfsjk
Social:
• Facebook Page: https://www.facebook.com/travelingrobert
• Facebook Group: https://www.facebook.com/groups/Travelingrobert/
• Instagram: https://www.instagram.com/travelingrobert/
• X: https://twitter.com/travelingrobert
• TikTok: https://www.tiktok.com/@travelingrobert
🎹Music: https://music.apple.com/us/artist/robert-morales/569217341
👕Store: https://travelingrobert.myspreadshop.com/
🛒Amazon shopping list: https://www.amazon.com/shop/travelingrobert
🗺️Travel Map (work in progress) https://travelingrobert.com/map.php
⛺️Book hard to get campgrounds with Campnab https://campnab.com/r/yft9ft
0:00 Arriving in Chicago
2:20 The First Mile
15:10 Walking by the River
19:06 Deep Dish Pie with New Friends
21:00 Surfshark (sponsored)
23:02 Walking from McCormick
29:32 The Big Bus Double Decker Tour
33:12 Another Deep Dish Pie
37:10 The Magnificent Mile
42:34 The Rest of the Big Bus Tour
47:23 Walking to Millennium Park
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Disclaimer: Some product links are affiliate links which means if you buy something we’ll receive a small commission.
✈This video complies with FAA Part 107 rules
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