Title: Historic Route 66 Vacation Packages & Trips 2026/2026 from CA $500 | Expedia.ca [Historic Route 66 Travel Guide](https://expedia.ca/Historic-Route-66.dx702654640613646336)[Hotels in Historic Route 66](https://expedia.ca/Historic-Route-66-Hotels.d702654640613646336.Travel-Guide-Hotels)[Vacation Rentals in Historic Route 66](https://expedia.ca/Historic-Route-66-Vacation-Rentals.d702654640613646336.Travel-Guide-VacationRentals)[Flights to Historic Route 66](https://expedia.ca/Cheap-Flights-To-Historic-Route-66.d702654640613646336.Travel-Guide-Flights)[Historic Route 66 Car Rentals](https://expedia.ca/Car-Rentals-In-Historic-Route-66.d702654640613646336.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248621561870385/84ae69cd-06d7-48b8-a04a-f0221ac6efc7.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Historic Route 66 Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 Historic Route 66 Vacation Deals Price found within the past 48 hours. Click for updated prices. ![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### theWit Chicago, a Hilton Hotel Downtown Chicago CA $500 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,001 reviews) great staff...loved our stay. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnQgU3F5hKWtfar4KUKibZ9X0aZnamqw9yBu2v7FsHBku) ![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Emily Hotel Downtown Chicago CA $771 per person Feb 12 - Feb 15 found 16 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,264 reviews) Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay. Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=povcxfI1kKc6tB2V7mz6EQrbXzJ27hCYvDHBZ5GI-bscOfgrInGqZ80Hd_3Fphx2) ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8a983359_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $677 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) Room was spotless, all the kitchen amenities were provided such as a Nespresso machine with refills, electric kettle, dishes, utensils, pots, and pans. The refrigerator has a water dispenser inside full-size freezer microwave dishwasher. They provide dishwashing detergent and dish soap. Paper towels. Stackable washer and dryer they supply a single sample of laundry detergent to do laundry then you’re on your own. Aldi is on the first floor so if you need anything grocery is available. there is a café attached to the building. Workout area is immaculately cleaned every day. There is a game room a large area to watch TV. we did not bring our pet, but there is an area on the rooftop for pets to run around and there’s green space down below. A full basketball court and an area for children to play. it was winter so the pool and hot tub were closed. they provide fresh linens and towels as needed. They are very prompt and answer the phone quickly. The parking is secure and well lit. Location is in a safe neighborhood. Across the street is disco pancakes for breakfast. Target is just down the road and CVS and Jewel grocery stores. This is our second time staying. When we do stay, we stay about a week. It is quiet. Great views. Reviewed on Dec 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnXRg8KMpiWWn12cMoSwBbo5det8ZT5y_CegzTXacC5rP) ![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Grand Vacations Club Chicago Magnificent Mile Downtown Chicago CA $720 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (317 reviews) The room was beautiful and clean and a good city view of the city Reviewed on Nov 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=wfVl52Kb4qOSeVECiqdWnd3U8StCFdAXFNZ7NnsNxj6EubE-fLbBqYxx7eUWqBT_) ![Waldorf Astoria Chicago](https://images.trvl-media.com/lodging/3000000/2720000/2717600/2717582/1040fa3a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Waldorf Astoria Chicago Downtown Chicago CA $1,369 per person Feb 12 - Feb 16 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) The staff was amazing. Will be making a return stay. Reviewed on Nov 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-02-12/2026-02-16/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=2MaV768TBcz8HM99OhHJ6HWMRDY3B_EomvEiuxnzGv_rFVnv_u-6ERAGc56sBhzC) ## Ready to book your vacation to Historic Route 66? Choose your dates ## Historic Route 66 Hotel Deals ![Club Quarters Hotel, Central Loop, Chicago](https://images.trvl-media.com/lodging/1000000/570000/565800/565746/19b0236f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Club Quarters Hotel, Central Loop, Chicago 111 West Adams Street Chicago IL Fully refundableReserve now, pay when you stay CA $127 CA $149 total Dec 11 - Dec 12 includes taxes & fees 8.6/10 Excellent! (3,334 reviews) Clean room, very friendly and helpful staff Reviewed on Nov 26, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F12%2F2025&endDate=12%2F12%2F2025&selected=565746&PinnedHotelID=565746&HadPinnedHotel=true®ionId=702654640613646336) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL CA $132 CA $155 total Dec 18 - Dec 19 includes taxes & fees 8.4/10 Very Good! (5,334 reviews) The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ... Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=702654640613646336) ![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/f21f6764_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hilton Chicago/Magnificent Mile Suites 198 E Delaware Pl Chicago IL Fully refundableReserve now, pay when you stay CA $117 CA $137 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (3,408 reviews) Suite was roomy and spacious, the location wasn’t the best due to high traffic Reviewed on Nov 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true®ionId=702654640613646336) [See all 19,667 properties in Historic Route 66](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F12%2F2025&endDate=05%2F12%2F2025®ionId=702654640613646336) 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. ![](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 Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other ### Lodging - [5 Star Hotels in Quad Cities](https://www.expedia.ca/5Star-Quad-Cities-Hotels.s50-0-d603001.Travel-Guide-Filter-Hotels) - [Hotels near Lake Michigan](https://www.expedia.ca/Lake-Michigan-Hotels.0-l6338716-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Apart-Hotels.d6233674-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Bed-And-Breakfast.d6233674-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Cabins.d6233674-aaCabins.Travel-Guide-Accommodation) - [Chalets in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Chalets.d6233674-aaChalets.Travel-Guide-Accommodation) - [Condo Rentals in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Condos.d6233674-aaCondos.Travel-Guide-Accommodation) - [Adults Only Resorts & in Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley-Hotels-Adults-Only-Resorts.0-0-d6233674-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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[Southeast Iowa Hotels](https://www.expedia.ca/Southeast-Iowa-Hotels.d6234151.Travel-Guide-Hotels) ### Flights - [Flights to Ohio River Valley](https://www.expedia.ca/Cheap-Flights-To-Ohio-River-Valley.d6233674.Travel-Guide-Flights) - [Flights to Quad Cities](https://www.expedia.ca/Cheap-Flights-To-Quad-Cities.d603001.Travel-Guide-Flights) - [Flights to Southeast Iowa](https://www.expedia.ca/Cheap-Flights-To-Southeast-Iowa.d6234151.Travel-Guide-Flights) - [Flights from Calgary to Quad Cities](https://www.expedia.ca/lp/flights/178245/603001/calgary-to-quad-cities) - [Flights from Calgary to Ohio River Valley](https://www.expedia.ca/lp/flights/178245/6233674/calgary-to-ohio-river-valley) - [Flights from Chicago to Quad Cities](https://www.expedia.ca/lp/flights/178248/603001/chicago-to-quad-cities) - [Flights from Columbus to Quad Cities](https://www.expedia.ca/lp/flights/178251/603001/columbus-to-quad-cities) - [Flights from Dallas to Ohio River Valley](https://www.expedia.ca/lp/flights/178253/6233674/dallas-to-ohio-river-valley) - [Flights from Indianapolis to Quad Cities](https://www.expedia.ca/lp/flights/178266/603001/indianapolis-to-quad-cities) - [Flights from Miami to Ohio River Valley](https://www.expedia.ca/lp/flights/178286/6233674/miami-to-ohio-river-valley) - [Flights from Minneapolis - St. Paul to Quad Cities](https://www.expedia.ca/lp/flights/178287/603001/minneapolis-st-paul-to-quad-cities) - [Flights from Minneapolis - St. Paul to Ohio River Valley](https://www.expedia.ca/lp/flights/178287/6233674/minneapolis-st-paul-to-ohio-river-valley) - [Flights from Orlando to Ohio River Valley](https://www.expedia.ca/lp/flights/178294/6233674/orlando-to-ohio-river-valley) - [Flights from Seattle to Quad Cities](https://www.expedia.ca/lp/flights/178307/603001/seattle-to-quad-cities) - [Flights from Toronto to Quad Cities](https://www.expedia.ca/lp/flights/178314/603001/toronto-to-quad-cities) - [Flights from Toronto to Ohio River Valley](https://www.expedia.ca/lp/flights/178314/6233674/toronto-to-ohio-river-valley) - [Flights from Vancouver to Ohio River Valley](https://www.expedia.ca/lp/flights/178315/6233674/vancouver-to-ohio-river-valley) - [Flights from Edmonton to Quad Cities](https://www.expedia.ca/lp/flights/180002/603001/edmonton-to-quad-cities) - [Flights from Edmonton to Ohio River Valley](https://www.expedia.ca/lp/flights/180002/6233674/edmonton-to-ohio-river-valley) - [Flights from Québec City to Ohio River Valley](https://www.expedia.ca/lp/flights/180017/6233674/quebec-city-to-ohio-river-valley) - [Flights from Amarillo to Quad Cities](https://www.expedia.ca/lp/flights/371/603001/amarillo-to-quad-cities) - [Flights from Hamilton to Quad Cities](https://www.expedia.ca/lp/flights/3963/603001/hamilton-to-quad-cities) - [Flights from Fort Lauderdale to Ohio River Valley](https://www.expedia.ca/lp/flights/601750/6233674/fort-lauderdale-to-ohio-river-valley) - [Flights from Newark to Ohio River Valley](https://www.expedia.ca/lp/flights/601760/6233674/newark-to-ohio-river-valley) - [Flights from Buffalo to Quad Cities](https://www.expedia.ca/lp/flights/602674/603001/buffalo-to-quad-cities) - [Flights from Buffalo to Ohio River Valley](https://www.expedia.ca/lp/flights/602674/6233674/buffalo-to-ohio-river-valley) - [Flights from Birmingham to Ohio River Valley](https://www.expedia.ca/lp/flights/602981/6233674/birmingham-to-ohio-river-valley) - [Flights from Quad Cities](https://www.expedia.ca/lp/flights/603001/flights-from-quad-cities) - [Flights from Winnipeg to Quad Cities](https://www.expedia.ca/lp/flights/6141041/603001/winnipeg-to-quad-cities) - [Flights from Ohio River Valley](https://www.expedia.ca/lp/flights/6233674/flights-from-ohio-river-valley) ### Packages - [Lake Michigan](https://www.expedia.ca/Lake-Michigan-United-States-of-America.d6338716.Vacation-Attraction) - [Visit Ohio River Valley](https://www.expedia.ca/Ohio-River-Valley.dx6233674) - [Quad Cities Vacations](https://www.expedia.ca/Quad-Cities.d603001.Destination-Travel-Guides) - [Visit Quad Cities](https://www.expedia.ca/Quad-Cities.dx603001) - [Visit Southeast Iowa](https://www.expedia.ca/Southeast-Iowa.dx6234151) ### Cars - [Ace Rental Cars in Quad Cities](https://www.expedia.ca/Ace-Car-Rentals-In-Quad-Cities.d603001-c2.Car-Rental-Guide-Suppliers) - [Advantage Rent-A-Car Rental Cars in Ohio River Valley](https://www.expedia.ca/Advantage-Rent-A-Car-Car-Rentals-In-Ohio-River-Valley.d6233674-c3.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Quad Cities](https://www.expedia.ca/Avis-Car-Rentals-In-Quad-Cities.d603001-c41.Car-Rental-Guide-Suppliers) - [Car rentals near Quad Cities](https://www.expedia.ca/Car-Rentals-In-Quad-Cities.d603001.Car-Rental-Guide) - [Pickup Car Rentals in Ohio River Valley](https://www.expedia.ca/Pickup-Car-Rentals-In-Ohio-River-Valley.d6233674-tPickup.Car-Rental-Guide-Class) - [Thrifty Car Rental Rental Cars in Ohio River Valley](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Ohio-River-Valley.d6233674-c45.Car-Rental-Guide-Suppliers) ### Other - [Things to do in Quad Cities](https://www.expedia.ca/Things-To-Do-In-Quad-Cities.d603001.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFQUlEQVR4Xu3aQXLbOgyAYWa68LJH8FF0NOpoOoqO0KUXnvAFIAhCitIp3ky7iP9/UwcG+XmnJE1p/6ByHvyNQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIqIM9y6j5Gb61t5fax/DHSfsl0aY/ycXyX17WPYnXeDFJAzmsgvTpvBikg5zWQXp03f1ekzq/0xukufbj34xGxg7/ko3jHu0BAQEAkEA1EA/FsV7s5Uvubm0xtcS322NfRLv8YoqPjQQkEBET+AQEpICDW7xFNj8ctT7c0EJACMpdARiASCEj5n8hMR2v56Ydk+KNvgWggvgPih2QIAjK2QOx4A+kd31DkKUfijXf5Zx2k3agp4oHYqIH0QPp7ICDtfBcIiN54PK67enwrN3e/GJ2q82aQi9GpOm8GuRidqvNmkIvRqTpvBrkYnarzZpCL0ak6bwa5GJ2q8+aAXKTHW3v3k/c+jzca8rtAQC4COQUCchHIqe+L2PFbG09v7+Y768dP3erqaA87iwzsdfV9EJAeSG+Rgb2uvg8C0gPpLTKw19X3vy1ix5f+lR2fNx6Pb/al/AfzWvQvrlt7hL+49kAaCAiIprsgICAROT3QS7mPd4ZrN9pIt6z46cKWBQICIoGAgFwcB1HE/pjLHtUXN9pHebNn/MVBCQSkgYB82gXRQEDaGalf/oZ7CcfX64/SxNWPEkcSiAYC0gMBiYFoIPqH03Zcsxv1uCHSfOzbjXaw+aer9qVM5ksQEBANBGRM5kuQF0Wa36jZjT56yMAQvdHce397Iu56ICANRAMBAWkgWkCOz+Uxshb50m5ci/6G21x9oPtW/CgeCAgISBj58QYCAqLJA11/eJ7V8fSeN/ro2Pip2z5KCASkgVggIKd3QED0uPWQ33Dv8qgWd4wCUuyBLlvxo2g28kBAQEBALBAQ7YhIums3zjYZmNv6jTay1P2jZzyIjkBmIBoICEjv5RBt7tqN9ozXG/24bZXuFn+g21bpH8UDGYFIIGMMot0PWwWkL4GM8QsgT9mdx+VGHenvrpe+s8vcRvZRNPko41fjPvRAQEAkEBAQkNEZsRsfYVd/nrb0se+juHXM7rJAQECuAtFAPJCrXgWZx/0Zr499dWVkvdsz/uI7AXlHP4oHAgICArLIWyAg1iWyyXHPkLilbTJvbR83KhI/nQfSQEBAQEBAbEs6I7Yr7/TdUuZ/MNviWuyvwHTrU+IWEBAQEJDPgYCMpfnyInX1sd/aQ07e+1wf+6XcHKl97t8c2Ae2QEAuAgEBkUBAnnbAu8/3WkTWon/MtchrW7WPso2j9lO3BQICIoGAaCAgsjRfPmV3drzRuvctfcYvfW+X17W/3nzxcBdIAQGZN26+CCKBeCDhxs0XXwTR4/bDs9/4Npa7K70L8pBV3fJu8uYur+pYBQEBAem7IA1kLIPMl9eItfSdvf/wbFul/2/yj/6dQJNnvCJ2lwcyApFAQHpL3wHxQEC+QGSk6ZY940tH7E++HuKeA9ERCEgBAfkUiI5AZnajHI83zpawvI6RbunBEIiOZusYgcTjsSUsr2MEEo/HlrC8jhFIPB5bwvI6RiDxeGwJy+sYgcTjsSUsr2P0B8ixu0zlh2f9dbYsz1Hzn6d3WZVvDvQZr1v62A+BNJCDUEBAQEYg7eWRvxdIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUn0f5D8Xl3nTI1Mu1AAAAABJRU5ErkJggg==)