
Historic Route 66 Beach Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top flight + Beach hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.

Omni Chicago Hotel
Downtown Chicago
Price was NZ$3,491, price is now NZ$2,924 per person
NZ$2,924
per person
17 Aug - 22 Aug
found 20 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (1,799 reviews)
Service at the restaurant for brunch was excellent!
Reviewed on 14 June 2026

The Emily Hotel
Downtown Chicago
Price was NZ$4,304, price is now NZ$3,403 per person
NZ$3,403
per person
17 Aug - 22 Aug
found 20 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on.
The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful.
Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.
Reviewed on 8 June 2026

Level Chicago Fulton Market
Downtown Chicago
Price was NZ$4,254, price is now NZ$3,378 per person
NZ$3,378
per person
17 Aug - 22 Aug
found 20 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.
Reviewed on 14 June 2026

Le Méridien Essex Chicago
Downtown Chicago
Price was NZ$3,710, price is now NZ$3,133 per person
NZ$3,133
per person
17 Aug - 22 Aug
found 20 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Staff was friendly & welcoming. Room was comfortable. Great location!!
Reviewed on 8 June 2026

L7 Chicago by LOTTE
Downtown Chicago
Price was NZ$3,853, price is now NZ$3,310 per person
NZ$3,310
per person
17 Aug - 22 Aug
found 20 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.6/10 Exceptional! (4,126 reviews)
Property was in center of town..view from room was amazing, other than having to look at the trump tower daily everything was perfect! Room was clean and nice sized for three of us. Plenty of room. We had two window seats which were amazing.
Reviewed on 14 June 2026
Don't see what you're looking for?
See all available trips from Columbus to Historic Route 66
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
