Title: Historic Route 66 Fishing Holidays 2026 | Expedia.co.uk ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 Fishing Holidays ## Book a Fishing Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to £335 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 Packages 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. ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago £567 per person 23 Jan - 28 Jan found 8 hours ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,059 reviews) Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive. Reviewed on 19 Dec 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £900 per person 23 Jan - 28 Jan found 8 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £837 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £600 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Lobby is beautiful. My family and I enjoyed the hot tub. However, was disappointed in the cleanliness of our room. We arrived and one of the toilets looked as if it hadn’t been cleaned, there was visible urine on the toilet lid. We had called housekeeping and they showed up promptly to clean the toilet which was nice. Going onto the bathtub, there were short black hairs scattered in the tub when we first arrived, also indicating that it may not have been cleaned either. There was dust along the TV stand and all on top of the coffee maker and tray. On top of the cleanliness, we didn’t feel so safe. Upon checking into our room, the door handle didn’t have any problems. However coming back to our room at night after being out our door handle was very loose off the door, indicating that someone had tried to get in. We called and had someone come fix it. Overall, not sure if I will be returning to this hotel. I had booked this hotel because I have stayed here before and it was a great experience at that time but was kind of embarrassing to bring my family here. Reviewed on 19 Dec 2025 ![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pendry Chicago Downtown Chicago £567 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,130 reviews) Excellent location to stay in the heart of the city. Reviewed on 17 Dec 2025 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Fishing holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £798 per person 3 Feb - 6 Feb found 21 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago Save 100% on your flight £900 per person 23 Jan - 28 Jan found 8 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![Four Seasons Hotel Chicago](https://images.trvl-media.com/lodging/1000000/30000/25800/25748/7da48e89_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Four Seasons Hotel Chicago Downtown Chicago £1,109 per person 23 Jan - 28 Jan found 8 hours ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (999 reviews) Very nice amenities and wellness facility. High end shopping within a very short walk. Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=LGW&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Fishing holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Hilton Chicago](https://images.trvl-media.com/lodging/1000000/20000/12600/12570/274f52b9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago Downtown Chicago £600 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 8.4/10 Very Good! (2,301 reviews) Lobby is beautiful. My family and I enjoyed the hot tub. However, was disappointed in the cleanliness of our room. We arrived and one of the toilets looked as if it hadn’t been cleaned, there was visible urine on the toilet lid. We had called housekeeping and they showed up promptly to clean the toilet which was nice. Going onto the bathtub, there were short black hairs scattered in the tub when we first arrived, also indicating that it may not have been cleaned either. There was dust along the TV stand and all on top of the coffee maker and tray. On top of the cleanliness, we didn’t feel so safe. Upon checking into our room, the door handle didn’t have any problems. However coming back to our room at night after being out our door handle was very loose off the door, indicating that someone had tried to get in. We called and had someone come fix it. Overall, not sure if I will be returning to this hotel. I had booked this hotel because I have stayed here before and it was a great experience at that time but was kind of embarrassing to bring my family here. Reviewed on 19 Dec 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £750 per person 28 Feb - 3 Mar found 1 day ago Return direct flight included London (LHR) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £798 per person 3 Feb - 6 Feb found 21 hours ago Return direct flight included London (LGW) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=LHR&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Fishing holidays in Historic Route 66 Price found within the past 48 hours. Click for updated prices. ![Palmer House a Hilton Hotel](https://images.trvl-media.com/lodging/1000000/10000/8100/8079/7f542141_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Palmer House a Hilton Hotel Downtown Chicago £1,106 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 8.4/10 Very Good! (2,059 reviews) Easy check in & out. Nice clean room, pool, & hotel. Hotel is old but that lends to a bit of nostalgia as maintenance & upkeep have keep the feeling of freshness alive. Reviewed on 19 Dec 2025 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/209f8cff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago £1,364 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) From staff to room it was a amazing experience. Reviewed on 18 Dec 2025 ![The Peninsula Chicago](https://images.trvl-media.com/lodging/1000000/590000/581300/581213/f1144862_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Peninsula Chicago Downtown Chicago £1,442 per person 7 Feb - 11 Feb found 1 day ago Return direct flight included London (LON) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Rooms were cozy and comfortable!!!! The staff was very welcoming, we visited in the month of December the Christmas decor was 100% amazing Reviewed on 16 Dec 2025 Don't see what you're looking for? See all available trips from London to Historic Route 66 [View all trips](https://expedia.co.uk/go/package/search/FlightHotel/2026-01-19/2026-01-26/?FromAirport=LON&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## More holidays you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Holidays [](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Holidays [](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Holidays [](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Holidays [](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click) ![gay friendly holiday packages](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ+ Holidays [](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Holidays [](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Holidays [](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Pet Friendly Holidays [](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ## More Holiday Ideas [Flights to Historic Route 66 ](https://expedia.co.uk/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[ Historic Route 66 Hotels ](https://expedia.co.uk/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[ Historic Route 66 Holiday Rentals ](https://expedia.co.uk/Historic-Route-66-Holiday-Rentals.d702654640613646336.Travel-Guide-HolidayRentals)[ Historic Route 66 Car Hire ](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Historic-Route-66.d702654640613646336.Car-Hire-Guide)[ Historic Route 66 Holidays ](https://expedia.co.uk/Historic-Route-66.d702654640613646336.Holidays-City-Breaks) \* Savings based on package bookings compared to the price of the same components booked separately. 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