Cruising Route 66: Five Hilton Hotels That Make the Drive Worth Stopping For
America is falling back in love with the road trip. A recent survey found that 71% of U.S. travelers plan to drive on their next vacation, and nearly two-thirds say they won’t go more than five hours without checking into a hotel. With Route 66 celebrating its 100th anniversary, it’s the perfect moment to map out a classic cross-country journey.
We’ve picked five standout Hilton properties along the Mother Road, from Chicago to Santa Monica. Each stop offers a chance to earn points through the free Hilton Honors program—new members get 3,000 bonus points on their first three stays.
**Chicago, Illinois: Hilton Chicago** Start at the official beginning. The Hilton Chicago sits just steps from the Route 66 start sign on Adams Street. Built in 1927 as the Stevens Hotel—then the world’s largest—this 1,544-room landmark has been carefully restored. You’ll get Grant Park and Lake Michigan views, modern rooms, and solid dining.
**Tulsa, Oklahoma: Tulsa Club Hotel, Curio Collection by Hilton** This 96-room boutique lives inside the 1927 Tulsa Club Building, an Art Deco gem. Renovated in 2019, it keeps its old-school glamour with a speakeasy lounge and sleek design. It’s a stylish pit stop with a fitness center and on-site restaurant.
**Santa Fe, New Mexico: Hilton Santa Fe Historic Plaza** History deepens at this 350-year-old hacienda. Southwestern details like a kiva fireplace, wood beams, and patterned rugs create a warm, authentic feel. It’s a quiet contrast to Tulsa’s jazz-age vibe.
**Flagstaff, Arizona: DoubleTree by Hilton Flagstaff** Sitting right on Old Route 66, this hotel is your base for the Grand Canyon (90 minutes away) and Arizona Snowbowl (10 miles). Expect a 24-hour gym, outdoor pool, hot tubs, and seasonal Southwestern fare. Plus, those signature DoubleTree cookies.
**Santa Monica, California: Hilton Santa Monica Hotel & Suites** End at the Pacific. Three blocks from the pier and ocean, this hotel channels California cool with bright decor, cabanas, farm-to-table food, and craft cocktails. Rooms feature white linens and light wood accents.
The Hilton Honors program adds value at every stop: digital keys, free Wi-Fi, late checkout, room upgrades, and free nights. Rates vary by season. Check Hilton.com for details.