Historic Route 66 Fishing Holidays
Book a Fishing Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £335 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 easyPackages with flights are ATOL protected
Top flight + Fishing hotel deals in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,193, price is now £916 per person
£916
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.
Reviewed on 10 Apr 2026
Pendry Chicago
Downtown Chicago
Price was £1,739, price is now £1,343 per person
£1,343
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on 7 Apr 2026
Level Chicago Fulton Market
Downtown Chicago
Price was £1,276, price is now £1,005 per person
£1,005
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on 10 Apr 2026
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was £1,574, price is now £1,299 per person
£1,299
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,026 reviews)
Wonderful hotel. Great location at a great price.
Reviewed on 1 Apr 2026
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all trips4 Night Fishing holidays in Historic Route 66
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was £1,193, price is now £916 per person
£916
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The place was beautiful. Breakfast was lovely and I enjoyed everything.
Reviewed on 10 Apr 2026
Pendry Chicago
Downtown Chicago
Price was £1,739, price is now £1,343 per person
£1,343
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,123 reviews)
The staff at the Pendry are top notch. We arrived early and just wanted to drop our bags off, but the staff was able to check us in several hours early. Upon learning it was my birthday, the bell hop brought me a glass of wine from the bar and later, the staff sent up a bottle of prosecco and birthday cupcakes. Our room
Reviewed on 7 Apr 2026
Level Chicago Fulton Market
Downtown Chicago
Price was £1,276, price is now £1,005 per person
£1,005
per person
10 May - 14 May
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago
Reviewed on 10 Apr 2026
Don't see what you're looking for?
See all available trips from London to Historic Route 66
View all tripsMore holidays you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
