Name: Eurostars Magnificent Mile
Price range: $110 total

Historic Route 66 flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$207

per person

Feb 20 - Feb 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

The Westin Michigan Avenue Chicago

Downtown Chicago

$538

per person

Jan 14 - Jan 18

found 23 hours ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

$685

per person

Mar 2 - Mar 6

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

Save 100% on your flight

$301

per person

Feb 14 - Feb 16

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.

Sandia Resort And Casino

Northeast Heights

Save 100% on your flight

$952

per person

Jan 13 - Jan 20

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Albuquerque (ABQ)

This smoke-free resort features a golf course, a casino, and a full-service spa. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and airport shuttle. Valet parking is free for guests, and you can enjoy a meal in one of the 5 restaurants.

Top Historic Route 66 hotels deals

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Free Cancellation

$87 nightly

$102 total

Dec 21 - Dec 22

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$81 nightly

$95 total

Jan 6 - Jan 7, 2026

Total with taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

Dec 21 - Dec 22

Total with taxes and fees

This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A library, express check-in, and express check-out are also on offer.

Free WiFi

Air conditioning

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$136 nightly

$155 total

Dec 21 - Dec 22

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and limo/town car service.

Pool

Spa

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Dec 29 - Dec 30

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Eurostars Magnificent Mile

660 North State Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$94 nightly

$110 total

Jan 12 - Jan 13, 2026

Total with taxes and fees

A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.

Spa

Free WiFi

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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.