Plan, book, travel with confidence
Better together
Save up to €150 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Where to stay in Historic Route 66
Find the best Historic Route 66 areas and neighborhoods for the activities you enjoy most. Learn more about Historic Route 66
Downtown Chicago
2 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Millennium Park are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Top hotels in Historic Route 66
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 4 Jul to 5 Jul
€160
per night
4 Jul - 5 Jul
8.4/10 Very Good! (3,077 reviews)
"Front desk help was amazing"
Reviewed on 2 Jun 2024
Central Loop Hotel
111 West Adams Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €160 per night from 4 Jul to 5 Jul
€160
per night
4 Jul - 5 Jul
8.4/10 Very Good! (1,625 reviews)
"My Go To place in downtown Chicago. Fantastic location, totally professional"
Reviewed on 1 Jun 2024
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €177 per night from 16 Jun to 17 Jun
€177
per night
16 Jun - 17 Jun
7.6/10 Good! (6,839 reviews)
"Perfect location to museum and restaurants. Good for family and friends"
Reviewed on 3 Jun 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Popular places to visit
Wrigley Field
4.5/5(40 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
McCormick Place
4.5/5(36 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Navy Pier
4/5(125 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
More trip options
- Las Vegas Holidays
- New York Holidays
- Orlando Holidays
- Chicago Holidays
- Los Angeles Holidays
- Miami Holidays
- Boston Holidays
- Nashville Holidays
- Houston Holidays
- San Francisco Holidays
- New Orleans Holidays
- Atlanta Holidays
- San Antonio Holidays
- Seattle Holidays
- Atlantic City Holidays
- Fort Lauderdale Holidays
- Dallas Holidays
- Washington Holidays
- Austin Holidays
- Denver Holidays
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.