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Embark on a nostalgic journey along Historic Route 66, a legendary highway that stretches from Chicago to Santa Monica, offering a unique travel experience through the heart of America. Known as the "Main Street of America," this iconic route is dotted with charming towns and vibrant cities, each offering a glimpse into the past. Travelers can find a variety of accommodations ranging from vintage motels to modern hotels, ensuring a comfortable stay along the way.
Some of the best neighborhoods to stay include the vibrant city of Chicago, the historic town of Springfield, Missouri, and the artistic community of Santa Fe, New Mexico. Each location offers its own unique attractions and local culture.
Top attractions along Route 66 include the Gateway Arch in St. Louis, the Petrified Forest National Park in Arizona, and the Santa Monica Pier in California. Whether you're a history buff or a road trip enthusiast, Route 66 promises an unforgettable adventure.
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Hotel in River North, Chicago · 45.39 mi from centre
8.8
450 reviews
A stay at Level Chicago - River North places you in the heart of Chicago, within a 10-minute walk of Merchandise Mart and State Street. This hotel is 0.8 mi (1.4 km) from Michigan Avenue and 0.9 mi (1.5 km) from Chicago Riverwalk.

Hotel in Rosemont · 45.40 mi from centre
9.2
1,631 reviews
Breakfast available
With a stay at Loews Chicago O'Hare Hotel in Rosemont (O'Hare), you'll be a 1-minute drive from Donald E. Stephens Convention Center and 5 minutes from Allstate Arena. This family-friendly hotel is 12 mi (19.3 km) from Wrigley Field and 13.2 mi (21.2 km) from Northwestern University.

Hotel in The Loop, Chicago · 45.41 mi from centre
9.0
944 reviews
Breakfast available
With a stay at Renaissance Chicago Downtown Hotel in Chicago (Downtown Chicago), you'll be steps from State Street and 5 minutes by foot from Michigan Avenue. This hotel is 0.3 mi (0.5 km) from Chicago Riverwalk and 0.4 mi (0.7 km) from Millennium Park.

Hotel in River North, Chicago · 45.45 mi from centre
9.0
983 reviews
Breakfast available
With a stay at The Westin Chicago River North, you'll be centrally located in Chicago, within a 10-minute walk of Chicago Theatre and Chicago Riverwalk. This luxury hotel is 0.8 mi (1.3 km) from Millennium Park and 0.9 mi (1.5 km) from Michigan Avenue.

Hotel in The Loop, Chicago · 45.50 mi from centre
9.0
1,813 reviews
Breakfast available
With a stay at Hilton Garden Inn Chicago Downtown Riverwalk in Chicago (Downtown Chicago), you'll be steps from Michigan Avenue and Chicago Riverwalk. This hotel is 0.3 mi (0.4 km) from Millennium Park and 0.8 mi (1.2 km) from Grant Park.

Hotel in Rosemont · 45.54 mi from centre
8.8
930 reviews
Breakfast available
With a stay at Aloft Chicago O'Hare in Rosemont (O'Hare), you'll be steps from Fashion Outlets of Chicago and 4 minutes by foot from Parkway Bank Park Entertainment District. This hotel is 0.2 mi (0.4 km) from Rosemont Theatre and 0.4 mi (0.7 km) from Donald E. Stephens Convention Center.

Hotel in River North, Chicago · 45.57 mi from centre
9.0
1,193 reviews
Breakfast available
With a stay at Hyatt Place Chicago/River North, you'll be centrally located in Chicago, steps from State Street and 7 minutes by foot from Michigan Avenue. This hotel is 0.5 mi (0.8 km) from Chicago Riverwalk and 0.4 mi (0.7 km) from Merchandise Mart.

Hotel in River North, Chicago · 45.62 mi from centre
7.6
934 reviews
Breakfast available
With a stay at Best Western River North Hotel in Chicago (Downtown Chicago), you'll be within a 5-minute drive of Michigan Avenue and Water Tower Place. This hotel is 1.1 mi (1.7 km) from Millennium Park and 1.2 mi (1.9 km) from Willis Tower.

Hotel in Rosemont · 45.62 mi from centre
8.6
1,895 reviews
Breakfast available
With a stay at Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG in Rosemont (O'Hare), you'll be a 4-minute walk from Donald E. Stephens Convention Center and within a 5-minute drive of Allstate Arena. This hotel is 11.8 mi (18.9 km) from Wrigley Field and 13 mi (20.9 km) from Northwestern University.

Hotel in Chicago · 45.66 mi from centre
9.2
813 reviews
Breakfast available
With a stay at Hyatt Place Chicago/Wicker Park in Chicago (West Town), you'll be within a 5-minute drive of United Center and Michigan Avenue. This hotel is 3.2 mi (5.2 km) from Lake Michigan and 3.2 mi (5.2 km) from Wrigley Field.

Hotel in Rosemont · 45.69 mi from centre
8.4
961 reviews
Breakfast available
Located in Rosemont (O'Hare), DoubleTree by Hilton Chicago O'Hare Airport - Rosemont is a 3-minute walk from Donald E. Stephens Convention Center and 5 minutes by foot from Rosemont Theatre. This hotel is 0.5 mi (0.7 km) from Fashion Outlets of Chicago and 0.6 mi (0.9 km) from Parkway Bank Park Entertainment District.

Hotel in Rosemont · 45.73 mi from centre
8.6
999 reviews
Breakfast available
With a stay at Embassy Suites by Hilton Chicago O'Hare Rosemont in Rosemont (O'Hare), you'll be within a 5-minute walk of Donald E. Stephens Convention Center and Rosemont Theatre. This hotel is 0.4 mi (0.7 km) from Fashion Outlets of Chicago and 0.6 mi (0.9 km) from Parkway Bank Park Entertainment District.

Hotel in River North, Chicago · 45.75 mi from centre
8.6
854 reviews
Breakfast available
With a stay at Homewood Suites by Hilton Chicago-Downtown, you'll be centrally located in Chicago, steps from State Street and 3 minutes by foot from Michigan Avenue. This hotel is 0.4 mi (0.6 km) from Chicago Riverwalk and 0.7 mi (1.1 km) from Millennium Park.

Hotel in River North, Chicago · 45.76 mi from centre
8.2
3,481 reviews
Breakfast available
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from Michigan Avenue. This hotel is 0.5 mi (0.8 km) from Chicago Riverwalk and 0.5 mi (0.8 km) from Chicago Theatre.

Hotel in River North, Chicago · 45.76 mi from centre
8.8
1,547 reviews
ACME Hotel Company is centrally located in Chicago, a 3-minute walk from Michigan Avenue and 12 minutes by foot from John Hancock Center. This boutique hotel is 0.8 mi (1.3 km) from Millennium Park and 1.1 mi (1.7 km) from Art Institute of Chicago.

Hotel in River North, Chicago · 45.76 mi from centre
9.4
969 reviews
Breakfast available
With a stay at The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago in Chicago (Downtown Chicago), you'll be steps from Michigan Avenue and 8 minutes by foot from Chicago Riverwalk. This luxury hotel is 0.6 mi (1 km) from Millennium Park and 0.2 mi (0.3 km) from State Street.

Hotel in The Loop, Chicago · 45.77 mi from centre
8.6
53 reviews
Breakfast available
With a stay at The St. Regis Chicago, you'll be centrally located in Chicago, within a 10-minute walk of Grant Park and Michigan Avenue. This luxury hotel is 0.5 mi (0.9 km) from Millennium Park and 0.6 mi (1 km) from Chicago Riverwalk.

Hotel in Rosemont · 45.77 mi from centre
8.4
963 reviews
Breakfast available
Located in Rosemont (O'Hare), Hilton Rosemont Chicago O'Hare is within a 10-minute walk of Donald E. Stephens Convention Center and Parkway Bank Park Entertainment District. This hotel is 0.5 mi (0.8 km) from Rosemont Theatre and 0.6 mi (1 km) from Fashion Outlets of Chicago.

Hotel in Streeterville, Chicago · 45.81 mi from centre
8.2
1,236 reviews
Breakfast available
With a stay at Sheraton Grand Chicago Riverwalk, you'll be centrally located in Chicago, a 6-minute walk from Michigan Avenue and 11 minutes by foot from Millennium Park. This eco-certified hotel is 0.7 mi (1.2 km) from Art Institute of Chicago and 0.8 mi (1.3 km) from John Hancock Center.

Hotel in Near North Side, Chicago · 45.83 mi from centre
8.6
952 reviews
Breakfast available
A stay at Chicago Marriott Downtown Magnificent Mile places you in the heart of Chicago, within a 5-minute drive of Art Institute of Chicago and Merchandise Mart. This hotel is 1.1 mi (1.8 km) from Chicago Children's Museum and 1.5 mi (2.3 km) from Navy Pier.