Title: Miles Vacation Packages & Trips 2025/2026 from CA $525 | Expedia.ca [Hotels in Miles](https://expedia.ca/Miles-Hotels.d553248634983438891.Travel-Guide-Hotels)[Vacation Rentals in Miles](https://expedia.ca/Miles-Vacation-Rentals.d553248634983438891.Travel-Guide-VacationRentals)[Miles Car Rentals](https://expedia.ca/Car-Rentals-In-Miles.d553248634983438891.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248634983438891/92ef23ce-6fcd-4aaa-9a36-fb275e9cf2a4.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Miles Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Richard Remington - ## 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 Miles Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $525 per person Jan 21 - Jan 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,248 reviews) Really cool modern space Reviewed on Nov 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-21/2026-01-24/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=PH-jGx-y6XL1TSuqeCJyC-VmQE8P_yg8NrQyQX9x3lzwj-h7XtlVj0hMVlnAXmbn) ![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 CA $887 per person Dec 23 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,110 reviews) We loved the Pendry! Reviewed on Oct 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=wluxj3LmHwzjyjRLnm-i-dF4XkXRZNs1Jjb4jyz3F4ciJmVsGobM3n2ALDGRurVe) ![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 $676 per person Dec 23 - Dec 29 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) A+++ in all areas. And fabulous location. Reviewed on Nov 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=wluxj3LmHwzjyjRLnm-i-csXdphYEIZK6utZlezf_dbgkggC00bb69tVE4ELPqNH) ![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 CA $802 per person Jan 21 - Jan 24 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,761 reviews) The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property. Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-21/2026-01-24/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=PH-jGx-y6XL1TSuqeCJyC-VmQE8P_yg8NrQyQX9x3lxFjNtAxzRlvfeYMg4DTZU2) ![Level Chicago - River North](https://images.trvl-media.com/lodging/75000000/74510000/74500500/74500458/668d065a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago - River North Downtown Chicago CA $723 per person Jan 28 - Feb 2 found 5 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (721 reviews) Love love loveeeee it here! Amazing location and views, feels like home away from home. Absolute best pool in the city. Feels like a Miami resort! One of my favvvvv place to be. Reviewed on Nov 6, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-28/2026-02-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=74500458&paandie=true&dealMarker=bU6Xn2PY1Z5eUu6jjLzX6QbakKbmOpA66Cl7BDsXdJJ2uVA97pGdd9oZqOdTpW_a) ## Ready to book your vacation to Miles? Choose your dates ## Miles Hotel Deals ![Stoney Creek Inn Galena](https://images.trvl-media.com/lodging/2000000/1110000/1109500/1109416/1ac5d099_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stoney Creek Inn Galena 940 Galena Square Dr, Galena, IL Fully refundableReserve now, pay when you stay 9.2/10 Wonderful! (1,261 reviews) Easy check-in clean room quiet Nice hot tub Reviewed on Nov 2, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=1109416&PinnedHotelID=1109416&HadPinnedHotel=true®ionId=553248634983438891) [](https://expedia.ca/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=1109416&PinnedHotelID=1109416&HadPinnedHotel=true®ionId=553248634983438891) ![Irish Cottage Inn & Suites](https://images.trvl-media.com/lodging/62000000/61520000/61517800/61517759/1d68f8be_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Irish Cottage Inn & Suites 9853 US-20, Galena, IL Fully refundableReserve now, pay when you stay CA $140 CA $195 total Nov 11 - Nov 12 includes taxes & fees 9.4/10 Exceptional! (1,216 reviews) Very nice place with excellent amenities and services. Love the live music and the Spa is first rate! Reviewed on Nov 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=61517759&PinnedHotelID=61517759&HadPinnedHotel=true®ionId=553248634983438891) ![Chestnut Mountain Resort](https://images.trvl-media.com/lodging/7000000/6260000/6256300/6256296/d04ca2aa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chestnut Mountain Resort 8700 W Chestnut Mountain Rd, Galena, IL 8.4/10 Very Good! (1,040 reviews) It has the most beautiful views. Very peaceful ! Reviewed on Nov 2, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=6256296&PinnedHotelID=6256296&HadPinnedHotel=true®ionId=553248634983438891) [](https://expedia.ca/Hotel-Search?startDate=21%2F11%2F2025&endDate=22%2F11%2F2025&selected=6256296&PinnedHotelID=6256296&HadPinnedHotel=true®ionId=553248634983438891) [See all 722 properties in Miles](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F11%2F2025&endDate=09%2F11%2F2025®ionId=553248634983438891) 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 \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)