Historic Route 66 Scuba Diving Holidays 2026

Plan, book, travel with confidence
Better together
Save up to AU$2,500 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

Top flight + Scuba Diving hotel deals in Historic Route 66

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

Swissotel - Chicago

Downtown Chicago

AU$3,287

per person

27 Dec - 3 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

9/10 Wonderful! (3,523 reviews)

The first room I checked in to had the door not flushly closing, and looked like someone had pried their way into the room. I checked in at 2:30am after driving from the Green Bay Packers football game in Green Bay, and they insisted that I check out at 11am. After two or three calls, they managed to delay it to 12:30pm. They want a $100 an hour for every hour you stay in the room after 11am and they very aggressively enforce it. I did not pay this amount and won't be staying at this hotel again and recommend that they change their customer service approach or clients will be choosing other hotels.

Reviewed on 21 Oct 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

AU$4,794

per person

27 Dec - 3 Jan

found 1 day ago

Return direct flight included

Sydney (SYD) to Chicago (ORD)

9.6/10 Exceptional! (2,035 reviews)

Our stay was fabulous! Curtis, who checked us in (and out), was so helpful with food recommendations and like all staff we encountered, so very nice! Room was impeccably clean and quiet with amazing views! Can’t wait til our next stay

Reviewed on 20 Oct 2026