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Chicago offers a variety of historic hotels that reflect the city's rich architectural heritage, perfect for travelers on the Route 66 road trip. Expect elegant accommodations with vintage charm, often located near iconic landmarks such as the Willis Tower and Millennium Park, along with modern amenities and unique dining options.

Downtown Chicago

Sitting on Michigan Avenue and the Chicago River in a historic landmark building, LondonHouse features Chicago’s only tri-level rooftop bar. The hotel is less than 10 minutes’ walk from Millennium Park.

All spacious guest rooms at the LondonHouse Chicago include free WiFi, a large work station and a 55 inch flat-screen TV. Some rooms include Chicago skyline and historic landmark views.

The 24-hour fitness centre includes stat-of-the-art equipment, ballet bar and more. Professionals will enjoy the flexible meeting spaces while events in the grand ballroom with stunning views are available as well.

The on-site LH offers a view with reimagined regional cuisine and cocktails. It includes a one-of-a-kind terrace overlooking the river and dining underneath the 23rd story domed cupola.

Navy Pier and the Art Institute of Chicago are each within 2 km of the LoundonHouse Chicago, Curio Collection by Hilton.

LondonHouse Chicago, Curio Collection by Hilton

Featuring stunning views of Lake Michigan, the Chicago Drake hotel is 3 minutes' walk from Oak Street Beach and 1 mile from Navy Pier. This hotel built in 1920 includes elegantly designed guest rooms and a chance to enjoy an afternoon tea or cocktails at Palm Court.

Each spacious room at The Drake provides deluxe bedding and marble bathrooms. Guest rooms offer a flat-screen HD TV with HBO and an iPod docking station.
Guests at the Drake Hilton Hotel can explore the shops located on the arcade level of the hotel. A convenience store and foreign currency exchange services are also available.

Lincoln Park Zoo is 2.4 miles from this hotel in Chicago. The John Hancock Center is less than 5 minutes' walk away.

The Drake Hotel

Just 1 block away from Millennium Park and the Art Institute of Chicago, this historic downtown hotel is located in Chicago’s theatre and financial district and offers on-site dining options, a modern business centre and spa services.

A flat-screen HDTV, desk and arm chair are offered in every modern guest room at Palmer House Hilton. t Housekeeping services are available upon request.

Guests can work out at the on-site fitness centre or visit the on-site spa.

Lockwood restaurant offers American cuisine for breakfast, lunch, and dinner. Amidst the historic lobby, guests can enjoy dinner & a crafted cocktail at the Lobby Bar.

The Monroe Red Line subway station is a 1-minute walk away, providing easy access to Chicago’s top attractions. Navy Pier is 2 miles away from the hotel.

Please note Red, Blue, Orange, Pink, Green, and Brown line train lines are all available immediately outside of the hotel for access to attractions and both airports.

The Palmer House Hilton

Just 1 block from the Magnificent Mile in Downtown Chicago, this historic European-style high-rise hotel boasts beautiful city views and offers free WiFi.

Each room at Hotel Saint Clair - Magnificent Mile includes a 32-inch flat-screen TV with premium cable channels and a coffee machine. A hairdryer is also provided.

Guests can get a taste of Chicago favorites at any of the popular restaurants located just a few blocks from the hotel. There is also a snack shop located on-site.

This hotel is an 8-minute walk from the Grand Avenue CTA red line station, providing easy access to Chicago attractions. The Shedd Aquarium is 1.6 miles away. The property is a 15-minute walk away from Navy Pier.

Hotel Saint Clair - Magnificent Mile

Situated amongst the shopping, dining and entertainment on the Magnificent Mile, this boutique hotel is located in the heart of downtown Chicago and offers historic architecture, on-site dining options and a 24-hour fitness centre.

The modern, stylish rooms at Warwick Allerton Hotel Chicago feature a flat-screen TV, iPod docking station and work desk. Guests can enjoy a drink from the room's minibar. Select rooms feature spectacular Magnificent Mile views.

12,000 square feet of on-site meeting and banquet space is available at the Warwick Allerton. The meeting spaces include luxury furnishings, modern technology and catering options. A 24-hour business centre and same-day laundry and dry-cleaning services are also offered.

Navy Pier, Millennium Park and the Art Institute of Chicago are all 1 mile away from the hotel. Water Tower shopping mall is 3 blocks away.

Warwick Allerton Chicago

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Historic Hotels in Chicago for Route 66 Road Trip

Parking

Restaurant

Pets allowed

Room service

Meeting/banquet facilities

24-hour front desk

Tennis court

Sauna

Fitness centre

Golf course (within 3 km)

Garden

Terrace

Non-smoking rooms

Airport shuttle

Fishing

Business centre

Babysitting/child services

Laundry

Dry cleaning

Continental breakfast

Facilities for disabled guests

Skiing

Barber/beauty shop

Family rooms

Games room

Casino

Breakfast in the room

Ironing service

Free parking

Internet services

Lift

Express check-in/check-out

Solarium

Safety deposit box

Valet parking

Currency exchange

Spa and wellness centre

Massage

Children's playground

Billiards

Table tennis

Karaoke

Windsurfing

Darts

Hot tub/Jacuzzi

Soundproof rooms

Canoeing

Hiking

Chapel/shrine

BBQ facilities

Packed lunches

Car hire

Cycling

Bowling

Tour desk

Hammam

Heating

Fax/photocopying

Diving

Horse riding

Squash

Snorkelling

Luggage storage

WiFi

Mini golf

Ski storage

Ski school

Allergy-free room

Indoor pool

Outdoor pool

Free WiFi

Non-smoking throughout

Air conditioning

Designated smoking area

ATM/cash machine on site

Private beach area

Restaurant (à la carte)

Restaurant (buffet)

Snack bar

Sun terrace

Outdoor pool (all year)

Outdoor pool (seasonal)

Indoor pool (all year)

Indoor pool (seasonal)

Concierge service

Entertainment staff

Nightclub/DJ

Private check-in/check-out

Shuttle service (free)

Shuttle service (additional charge)

Ski equipment hire on site

Ski pass vendor

Ski-to-door access

Special diet menus (on request)

Trouser press

Vending machine (drinks)

Vending machine (snacks)

Water sport facilities on site

Hot spring bath

General

Activities

Services

Room Amenities

Bathroom

Media & Technology

Food & Drink

Services & Extras

Outdoor & View

Internet

Kitchen

Outdoors

View

Living Area

Bedroom

Layout

Accessibility

Building characteristics

Pool and wellness

Transport

Reception services

Common areas

Entertainment and family services

Cleaning services

Business facilities

Shops

Miscellaneous

Bath/Hot spring

Hostel facilities

Safety & security

Your sustainability practices

Safety features

Hygiene

Physical distancing

Cleanliness & disinfecting

Food & drink safety

Self check-in

Exclusive services