Name: Hilton Chicago
Price range: $173 total

Historic Route 66 flight + hotel vacation packages

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

The Wildwood Hotel

Save 100% on your flight

$386

per person

Feb 15 - Feb 18

found 1 day ago

Roundtrip flight included

Dallas (DFW) to St. Louis (STL)

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Westgate Branson Woods Resort and Cabins

Shepherd of the Hills

Save 100% on your flight

$459

per person

Mar 2 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Springfield (SGF)

This smoke-free resort features 2 outdoor pools, an indoor pool, and a restaurant. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$590

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) 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.

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$593

per person

Mar 13 - Mar 16

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Still Waters Resort

Save 100% on your flight

$500

per person

Mar 2 - Mar 9

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Springfield (SGF)

A marina, 3 restaurants, and 3 hot tubs are all featured at this smoke-free condo resort. Bring the family and enjoy the mini golf, children's pool, and free theme park shuttle. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.

Top Historic Route 66 hotels deals

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Free Cancellation

$96 nightly

$113 total

Jan 1 - Jan 2, 2026

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

$89 nightly

$105 total

Jan 5 - Jan 6, 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

Palmer House a Hilton Hotel

17 E Monroe St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$156 nightly

$179 total

Jan 2 - Jan 3, 2026

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

Silversmith Hotel Chicago Downtown

10 S Wabash Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$149 total

Jan 4 - Jan 5, 2026

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

Club Quarters Hotel Wacker at Michigan, Chicago

75 E Wacker Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$103 total

Jan 12 - Jan 13, 2026

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

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$173 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

Pool

Hot Tub

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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.