🏙️ 1. Chicago – Where Route 66 Begins (in Style)

  • Stay: 🛌 The Peninsula Chicago or The Langham — both offer 5-star comfort with spa services and skyline views.

  • Dine: 🍽️ Gibsons Italia (high-end steak with river views) or Ever (Michelin-starred modern cuisine).

  • Experience:

    • Visit the Route 66 Begin Sign on Adams Street (photo op!).

    • Take a private architectural boat tour on the Chicago River.

    • Explore the Art Institute of Chicago, one of the finest art museums in the world.

🛤️ 2. Joliet – Retro Vibes Meets Modern Luxe

  • Stay: Harrah’s Joliet Casino & Hotel – upscale rooms and a full casino experience.

  • Dine: Juliet’s Tavern – a trendy downtown spot with refined takes on classic Midwest dishes.

  • Experience:

    • Private tour of the Rialto Square Theatre, a restored 1926 palace.

    • Check out the Route 66 Welcome Center and Old Joliet Prison (for a stylishly eerie photo stop).

🛣️ 3. Pontiac – Small Town Glam

  • Stay: Three Roses Bed & Breakfast – boutique luxury with antique flair.

  • Dine: Bernardi’s II – classic Italian with wine pairings in a cozy setting.

  • Experience:

    • Book a private tour of the Route 66 Hall of Fame Museum.

    • Explore the town's historic murals and museum campus via a chauffeured golf cart ride.

🚗 4. Bloomington-Normal – Sophisticated Stopover

  • Stay: Vrooman Mansion – a historic B&B with lavish rooms, gourmet breakfasts, and elegant décor.

  • Dine: Epiphany Farms Restaurant – upscale farm-to-table dining that’s big on flavor and sustainability.

  • Experience:

    • Visit the David Davis Mansion for a Gilded Age glimpse into Illinois politics and society.

    • Explore curated shopping boutiques in Uptown Normal.

🍷 5. Springfield – Presidential Luxury

  • Stay: Inn at 835 Boutique Hotel – an elegant former apartment house from the 1900s, now offering luxurious suites.

  • Dine: Obed & Isaac’s Microbrewery and Eatery or for fine dining, try Augie’s Front Burner.

  • Experience:

    • Book a private guided tour of the Abraham Lincoln Presidential Library & Museum.

    • Visit Lincoln’s Home with a VIP experience (some offer after-hours or private group tours).

    • Take a luxury carriage ride around the Old State Capitol.

🛍️ 6. Litchfield – Boutique Pit Stop

  • Stay: Baymont by Wyndham – best option for a plush night’s rest, or opt for a boutique suite via Airbnb.

  • Dine: Ariston Café – one of the oldest Route 66 restaurants, but opt for a gourmet twist with wine pairings.

  • Experience:

    • Tour the Route 66 Museum and shop for handcrafted vintage souvenirs at antique shops.

🌿 7. Edwardsville & Collinsville – Elegant End Before Missouri

  • Stay: Villa Marie Winery & Banquet Center (luxury suites, vineyard views).

  • Dine: Cleveland-Heath in Edwardsville – one of the best upscale dining spots in the area.

  • Experience:

    • Visit Cahokia Mounds, a UNESCO World Heritage Site, with a private docent-led tour.

    • Enjoy a luxury picnic with local wine and artisanal snacks on the grounds.

Bonus Luxury Touches Along the Way:

  • Private Chauffeur or Luxury Car Rental: Drive Route 66 in style with a classic car or luxury convertible.

  • Spa Stop: Book a treatment at a luxury spa in Bloomington or Chicago for a mid-route refresh.

  • Photographer-for-a-Day: Hire a pro to capture your road trip moments in a glam travelogue.