Route 66 Chicago Tour: 7 Historic Stops by Private Car

By the All Star Limo Service team

Last updated: November 6, 2026

Quick answer: Route 66 starts in Chicago, and the first 45 miles of it, from the Begin sign on Adams Street to the Joliet museum, run straight through the southwest suburbs All Star Limo Service calls home. We run it as a private chauffeured tour by the hour: a two-hour downtown signs-and-diner loop from $160, a half-day to Joliet from $480 in an SUV, or a full day for a group of 14 in a Sprinter for $1,200. You stop where you want, eat where you want, and nobody parks, navigates or drives home full of fried chicken. Pickup from your door in Orland Park, Tinley Park or Lemont, a Loop hotel, or O’Hare and Midway. Call or text (708) 998-6336.

Why Route 66 From the Southwest Suburbs Is a Different Tour

Every Route 66 tour sold in Chicago starts downtown and drives out, which means a family in Orland Park goes 40 minutes into the city to come 40 minutes back past their own exit. Our tour runs the other way when you want it to. We pick you up at home, drive in to the downtown stops in the morning while the Loop is quiet, then work back out along Ogden Avenue and Joliet Road, and the last stop in Joliet is 25 minutes from your driveway. No doubling back, no parking in the Loop, and the chauffeur has been eating at these stops for years.

The Seven Stops, in Order, With Time at Each

Addresses, what to do, and how long people actually stay. The alignment runs Adams Street west to Ogden Avenue, then Joliet Road, then Illinois 53 into Joliet.

Nobody eats at four restaurants in one day. Most groups pick Lou Mitchell’s for breakfast and one chicken stop for lunch, and photograph the rest.

Three Tours We Run, Timed and Priced

All three are hourly bookings, so you add a stop or skip one without a new quote. Hourly rates: executive sedan $80, Suburban $95, Escalade or Navigator $120, S-Class $130, Sprinter Jet (14) $150.

Fourteen friends on the full day in the Sprinter is about $85 each. Tolls are included; meals and admissions are yours. Hourly details and minimums: hourly limo rentals; the longer cost guide: hourly limo rental cost guide. Vehicles: fleet, and Escalade vs S-Class vs Sprinter if you are choosing.

A Sample Full Day From Orland Park

Run it in reverse from a Loop hotel and the chauffeur drops you back downtown at 4. From Loop limo service hotels the morning stops are five minutes apart.

Starting From the Airports or a Downtown Hotel

Practical Notes From the Chauffeurs Who Drive It

Why Book It With All Star

What Riders Say About All Star

5.0 stars from 51 Google reviews.

“The drivers know the area, the cars are new and clean. Recommended.” — Justin S., Google review

“New vehicles, a free upgrade to a larger car, and a kind, professional driver. I would book again.” — Kat A., Google review

“Amazing service, classy all around, first class. My go-to.” — Tony W., Google review

Read all 51 reviews on Google.

All Star Limo Service: Where We Are

Quick Facts

Related Services and Guides

• hourly limo rentals
• hourly limo rental cost guide
• Sprinter limo service
• group transportation
• fleet
• Escalade vs S-Class vs Sprinter
• Chicago limo costs
• Loop limo service
• Orland Park limo service
• Tinley Park limo service
• Lemont limo service
• Chicago airport limo service
• O’Hare limo service
• Midway limo service
• long layover at O’Hare
• Midway layover guide
• event limo service
• Chicago limousine travel guide

All Star Limo Service is a Chicago limousine and car service based in the southwest suburbs, serving Chicago, every suburb, O’Hare, Midway, Chicago Executive and DuPage airports, 24 hours a day. Call or text (708) 998-6336. Find us on Google.

About All Star Limo Service

We run the first 45 miles of Route 66 as a private tour by the hour from the southwest suburbs, downtown hotels and both airports, year-round. Our chauffeurs are background-checked, licensed and commercially insured, our fleet is late-model and owned by us, and we have served Chicago and the suburbs for more than ten years. Call or text (708) 998-6336, open 24 hours.

Frequently Asked Questions

How much does a private Route 66 tour from Chicago cost?

From $160 for two hours. See hourly limo rentals.

Where does Route 66 start in Chicago?

The Begin sign is on Adams Street at Michigan Avenue, across from the Art Institute; the End sign is a block south on Jackson. Navy Pier was named the centennial starting point.

Can we do all seven stops in one day?

Yes, in 7 to 8 hours from the southwest suburbs or downtown. Eat at two of the four restaurants and photograph the rest.

Which stops are the best for lunch?

Dell Rhea’s Chicken Basket in Willowbrook or White Fence Farm in Romeoville; both are fried chicken, both are on the original alignment, and groups usually pick one.

Can you pick us up in Orland Park and run the tour backward?

Yes. See Orland Park limo service and Tinley Park limo service.

Do you have a vehicle for a car club of 14?

Yes, the Sprinter Jet. See Sprinter limo service.

Can we start at O’Hare or Midway on a layover?

Yes. See O’Hare limo service and Midway limo service.

Does the chauffeur guide the tour?

The chauffeur knows the stops, the photo spots and the hours, and gets you to each one without a parking hunt. He is not a licensed tour guide; the stops tell their own stories.

Can we add or skip a stop on the day?

Yes. It is an hourly booking, so the only thing that changes is the clock.

Is the tour available in winter?

Yes, year-round. The stops are open, the car is warm, and the Begin sign photo looks better with snow.

Can we keep going past Joliet?

Yes. Wilmington’s Gemini Giant and Pontiac’s museum are another one to two hours southwest; ask when you book and we price the extra hours.

How far ahead should we book?

A week for a weekday; two weeks for a weekend in summer or the centennial events, when Sprinters go first.

How do I book?

Call or text (708) 998-6336, or book online.