Beginning a Route 66 journey in Chicago means stepping into nearly a century of American travel history.

The Mother Road officially debuted in 1926, envisioned as a single continuous roadway linking the Midwest to the Pacific. Their goal was simple but revolutionary: create a highway that connected rural towns to major cities, opening the American West to everyday travelers, not just rail passengers or the wealthy.

Chicago, already a major transportation hub with a booming population, was the natural choice for the eastern terminus of the new highway.

Route 66 hotels in ChicagoSable at Navy Pier, home to the centennial starting point of Route 66Palmer House, known for its ornate lobby bar and rich historyStaypineapple Chicago, housed inside an early skyscraperChicago Athletic Association Hotel, with rooftop views of the routes start pointOhio House Motel, a retro motel designed for 1960 roadtrippersHampton Inn Chicago, inside a former motor club buildingExplore more Chicago hotels offering special deals and packages for the Route 66 centennial.

Today, Chicago offers a range of hotels that make perfect launchpads for your westward adventure, including a range of historic properties that housed original Route 66 road-trippers during the highway’s heyday.

Check out six standout Chicago hotels that offer both comfort and a sense of place as you prepare to get your kicks on Route 66.

Sable at Navy PierBest for: Starting your Route 66 adventure at the lakefront’s new centennial start point

Photo by Mike SchwartzStaying at Sable at Navy Pier lets you literally wake up steps from the start of Route 66 — making it an ideal jumping off point for road trippers.

To honor the 100th anniversary of “The Mother Road,” the city of Chicago declared Navy Pier the new Route 66 Ceremonial Starting Point. The route now officially runs from pier to pier, as the end point is on Santa Monica Pier in Los Angeles.

Photo by Mike Schwartz

Route 66 Sign Dedication at Navy Pier

Navy Pier Inside the hotel, a nautical-inspired design and floor-to-ceiling windows create the feeling of floating above the waters of Lake Michigan. Guests can enjoy dinner at Lírica, the hotel’s Latin‑inspired restaurant or head upstairs to Offshore Rooftop for cocktails framed by the skyline.

Guests will also enjoy easy access to all of Navy Pier’s top attractions, including boat tours, live theatre, family-friendly rides, and the iconic Centennial Wheel.

Explore more: Check out top Chicago spots to eat along Route 66.

Palmer HouseBest for: Immersing yourself in Chicago history and lobby photo opsThe Palmer House is one of Chicago’s most storied hotels, originally opened in 1871 as a wedding gift from businessman Potter Palmer to his wife, Bertha Honoré Palmer.

Though the first building was destroyed in the Great Chicago Fire, it was rebuilt and reopened in 1873, making the Palmer House the country’s longest-operating hotel.

Its opulent lobby, decked out with Tiffany chandeliers and marble staircases, reflects the city’s Gilded Age ambition. Staying here places you just steps from the historic Adams Street start point, where Route 66 began for decades.

Before you head west, don’t miss tasting a piece of Chicago history: the brownie was invented right here at the Palmer House for the World’s Columbian Exposition in 1893. The original Palmer House brownie is served right inside the hotel at Lockwood Restaurant Bar, located on the lobby level.

Looking for a landmark stay? Explore more historic hotels in Chicago.

Staypineapple ChicagoBest for: Architecture lovers, shoppers, and foodiesHoused in the 1895 Reliance Building, Staypineapple Chicago occupies one of the most important early skyscrapers in the world.

The striking downtown building was a breakthrough in its time. It was one of the first to use an all‑steel skeletal frame, allowing for expansive windows and unprecedented height.

The building became a prototype for the twentieth‑century skyscraper, influencing architects worldwide and helping cement Chicago’s reputation as the birthplace of modern architecture.

The hotel’s prime location in the Loop makes it an easy walk to both the original Jackson Boulevard starting point and the later Adams Street alignment of Route 66. Theres also plenty to explore along historic State Street, just outside the hotel doors.

Inside, the hotel’s meticulously preserved details offer a glimpse into the city’s architectural revolution at the turn of the century. The buzzy new first-floor restaurant, Mariela, serves a coastal-inspired menu by a team of acclaimed Chicago chefs.

Chicago Athletic Association HotelBest for: Rooftop views and staying near the original 1926 starting point

The Drawing Room inside the Chicago Athletic Association; photo by Nick PodrazaBuilt in 1893, this stunning landmark sits along Michigan Avenue, just steps from where Route 66 originally began in 1926. Today, the spot is marked with a colorful pylon — perfect for your pre-road trip photo op.

The design of the Chicago Athletic Association building was inspired by a Venetian palace, with its pointed arches, intricate tracery, and richly ornamented façade. For decades, it served as an exclusive private men’s club whose members included some of the city’s most influential industrialists, politicians, and athletes.

Before you set off, hop in the elevator and head straight to Cindy’s, the hotel’s rooftop restaurant and bar. Grab a cocktail and enjoy one of the best views in the city: the lake, the park, and the very streets where the Mother Road once began.

Hampton Inn ChicagoBest for: Travelers who love Art Deco and motor history

Jacks Place Bar, Hampton Inn Suites hotel in downtown ChicagoThe Chicago Motor Club was founded in 1906 by early automobile enthusiasts who wanted safer streets, better roads, and reliable travel information. In the decades that followed, the club became one of the Midwest’s most influential advocates for motorists — publishing maps, posting road signs, lobbying for highway improvements, and offering travel planning long before GPS or standardized signage existed. The club’s work directly shaped the era in which Route 66 was born.

Today, the building lives on as the Hampton Inn Chicago, and checking in feels like stepping into a beautifully preserved tribute to the golden age of auto travel.

Much of the original Motor Club character remains intact. Guests can still admire the soaring lobby, the restored mural, the decorative metalwork, and the elegant mezzanine railings. A Ford Model A from 1928 — the same year the building opened — sits proudly on display, honoring the era when motorists came here for maps, roadside assistance, and advice before heading west.

Ohio House MotelBest for: Retro vibes and an authentic Route 66 experienceAn old-school motel surrounded by skyscrapers, the Ohio House Motel is the last remaining motor lodge in downtown Chicago. This historic spot is a rare survivor from the era when travelers pulled right up to their room doors and neon signs lit the way across America.

Built in 1960, the Ohio House reflects the rise of mid‑century “motor inns” that catered to the growing number of families and road‑trippers exploring the country by car. Its distinctive Googie‑style sign, angled rooflines, and drive‑up parking capture the optimism and mobility of the postwar years, the same cultural moment when Route 66 was at its peak and carrying millions of travelers westward.

While Chicago’s skyline transformed around it, the motel remained remarkably unchanged: it still operates as a motel, so guests can park directly outside their rooms and enjoy the classic mid‑century layout that has survived waves of redevelopment.

Though not located directly along Route 66, the Ohio House embodies the spirit of the Mother Road and feels like stepping into a 1960s road trip postcard — making it a fun, authentic choice for travelers who want to begin their Route 66 adventure with a dose of pure Americana.