Route 66 offers a true taste of America, and the culinary adventure kicks off here in Chicago, a city that offers some of the best bites in the U.S. For a century, travelers have fueled up here before heading west on this iconic road trip.

With the recent designation of Navy Pier as the official starting point of Route 66, visitors can now begin their journey at one of the city’s most iconic lakefront destinations. From there, the road winds through buzzing neighborhoods and historic corridors lined with beloved eateries that have fed generations of road‑trippers.

If you’re embarking on the full 2,448‑mile journey or simply exploring the first delicious miles, here are the must‑eat stops along Route 66 in Chicago and Chicagoland.

Dining near Navy Pier: the official start point of Route 66

Navy PierIn 2026, Chicago officially named Navy Pier the new eastern terminus of Route 66, creating a pier‑to‑pier connection with the Santa Monica Pier and making it the new go-to spot to enjoy a feast of iconic Chicago flavors before heading west.

Before you hit the road, take time to grab a bite and soak in the waterfront views. Grab a Chicago‑style hot dog at America’s Dog Burger, or lean into local history with a world-famous Cheezborger at the Billy Goat Tavern.

For a true taste of the citys neighborhoods without leaving the lakefront, pick up authentic Garibay Tamales, share a deep-dish stuffed pizza from Giordanos, or visit Harry Caray’s Tavern for BBQ and a dose of sports nostalgia.

Take in the sweeping views at Offshore Rooftop, or indulge in Garrett Popcorn’s classic ‘Chicago Mix’ as you stroll the Pier. Finally, finish on a sweet note with a five-flavor slice of The Original Rainbow Cone, a South Side tradition since 1926.

Lou MitchellsLou Mitchell’s565 W. Jackson Blvd., Chicago

No Route 66 food list is complete without Lou Mitchell’s, the legendary diner that has been feeding travelers since 1923. Known as the “first stop on the Mother Road,” Lou Mitchell’s serves hearty breakfasts, fresh‑baked pastries, and classic diner fare. Don’t miss the warm donut holes handed out as you walk in. It’s a Chicago institution and a rite of passage for anyone starting their Route 66 journey.

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The Berghoff17 W. Adams St., Chicago

Kick off the beginning of your road trip with a classic Chicago experience. Just steps from the original Route 66 route, The Berghoff has been serving German‑American comfort food since 1898. Think schnitzel, sauerbraten, and house‑brewed beer in a historic setting that feels like stepping back in time.

Al’s #1 Italian BeefMultiple locations, including 1079 W. Taylor St.

Chicago’s Italian beef sandwich is a culinary icon, and Al’s #1 Italian Beef is one of the best places to try it. Slow‑roasted beef, spicy giardiniera, and a jus‑soaked roll make for a messy, unforgettable meal. It’s pure Chicago — and the Little Italy location is a delicious detour just off the early miles of Route 66.

Connie’s Pizza2373 S. Archer Ave., Chicago

Deep dish pizza is a must for any Chicago visitor, and Connie’s Pizza has been a family‑owned favorite since 1963. Bonus: it sits right along the historic route. Their signature deep dish, with its buttery crust and rich tomato sauce is perhaps the most satisfying way to fuel up before hitting the open road.

Henry’s Drive‑In6031 Ogden Ave, Cicero

A beloved, old‑school hot dog stand thats been standing directly on Route 66 since 1950, Henry’s Drive-In is best known for its “Super Hot Dog” and neon‑bright signage.

Cigars Stripes BBQ Lounge6715 Ogden Ave, Berwyn

A rock‑’n’‑roll barbecue joint with a cult following, this one-of-a-kind “BBQ Lounge” is quirky, smoky, neon‑lit, and exactly the kind of offbeat stop Route 66 travelers adore. Great ribs, wings, and character for days.

Del Rhea’s Chicken Basket645 Joliet Rd., Willowbrook

Once you leave the city and enter Chicagoland, youll run into Del Rhea’s Chicken Basket — a Route 66 treasure. Open since the 1940s, this roadhouse is famous for its crispy fried chicken, neon sign, and vintage charm. It’s listed on the National Register of Historic Places and remains one of the most beloved stops on the Illinois stretch of the Mother Road.

White Fence Farm1376 Joliet Rd., Romeoville

Another fried chicken icon, White Fence Farm has been serving family‑style meals since the 1920s. The chicken is crisp; the sides are plentiful. It’s a perfect stop for families or groups traveling together. Check out the antique car collection in the lobby and the alpacas and mini goats out by the barn.