Title: Paoli Vacation Packages & Trips 2025/2026 from CA $653 | Expedia.ca [Hotels in Paoli](https://expedia.ca/Paoli-Hotels.d3000443084.Travel-Guide-Hotels)[Vacation Rentals in Paoli](https://expedia.ca/Paoli-Vacation-Rentals.d3000443084.Travel-Guide-VacationRentals)[Paoli Car Rentals](https://expedia.ca/Car-Rentals-In-Paoli.d3000443084.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Paoli 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 Paoli Vacation Deals Price found within the past 48 hours. Click for updated prices. ![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 $653 per person Jan 22 - Jan 26 found 19 hours ago Roundtrip non-stop flight included Montreal (YUL) 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/2026-01-22/2026-01-26/?FromAirport=YUL&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=RJ5_wbqy5uZlNCDNol6qSXjcY1Z5eaegFtWz3rnkPfJ43xIq5oM9AeZscllP-bFA) ![The Westin Michigan Avenue Chicago](https://images.trvl-media.com/lodging/1000000/30000/21100/21055/dcfbf36b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Michigan Avenue Chicago Downtown Chicago CA $819 per person Dec 27 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.8/10 Excellent! (1,070 reviews) Great trip! Will stay again. Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=21055&paandie=true&dealMarker=PHEtHAqLlHxy01HQpPCW1OSg0yth409x1S8oMJkL_vcKn-TrcmyXGu9LLDqiI_Z_) ![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 $1,183 per person Dec 26 - Jan 2 found 23 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (367 reviews) This was our first time at Level Chicago -Old Town. Last year we stayed at Level Chicago - North. Both apartments were really cozy and offered amazing views of the city. Old Town is a great place to stay, the staff overall was professional and polite. The unit was mostly clean, however, some of the towel were stained (seemed like he make up did not come off with bleach). It wasn't to my liking so I did not use them. Also, they knew we were six people but only gave 4 bath towels. I had to request additional. Another thing is that the locks in the bathroom and bedrooms were not working. It was a bit frustrating considering 6 people were sharing one bathroom. The apartment itself is very comfortable, has washer and dryer on site, which is convenient, especially when staying with children. The kitchen was equipped with all the basic needs except a good coffee machine. They have a nespresso machine but I would have rather an actual coffee machine not espresso machine. Safety was key. My family and I felt safe in the building and the area. Parking was not available in the building (the cost is $70 per night) but that wasnt an issue because we found plenty of parking right outside by the meters. Reviewed on Oct 29, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=39805843&paandie=true&dealMarker=Br8uQJZB120LWEepv4T_RT6GnfG-IqmhjMGYE4_xxVITMziOa_pnZnF7kqpQbsZi) ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $1,395 per person Dec 12 - Dec 16 found 22 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9.6/10 Exceptional! (1,006 reviews) This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend! Reviewed on Oct 20, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-16/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=y6XgmfqO1e9aS9tso3yZN5HlS79Jg7bnHUme94EcQjvo-JFq--f-uXnVl3Ub5729) ![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 $1,030 per person Dec 5 - Dec 7 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/2025-12-05/2025-12-07/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=PHEtHAqLlHxy01HQpPCW1Hmmxlv5k73Pe_8SI9aW7sWtm7LOmcwu4Pipe5mxhFnj) ## Ready to book your vacation to Paoli? Choose your dates ## Paoli Hotel Deals ![The Madison Concourse Hotel and Governor's Club](https://images.trvl-media.com/lodging/1000000/30000/28500/28447/fb616a0c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Madison Concourse Hotel and Governor's Club 1 W Dayton St, Madison, WI Fully refundableReserve now, pay when you stay CA $175 CA $202 total Nov 9 - Nov 10 includes taxes & fees 9.4/10 Exceptional! (3,257 reviews) Room was clean, check in and out was simple Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=28447&PinnedHotelID=28447&HadPinnedHotel=true®ionId=3000443084) ![Best Western Plus InnTowner Madison](https://images.trvl-media.com/lodging/1000000/10000/2000/1919/37b6debe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus InnTowner Madison 2424 University Avenue, Madison, WI Fully refundableReserve now, pay when you stay CA $164 CA $189 total Nov 9 - Nov 10 includes taxes & fees 9/10 Wonderful! (1,007 reviews) Close location to UW hospital, breakfast had a lot of hot and cold options. Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=1919&PinnedHotelID=1919&HadPinnedHotel=true®ionId=3000443084) ![Baymont by Wyndham Madison West/Middleton WI West](https://images.trvl-media.com/lodging/1000000/50000/40100/40004/75db6fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Madison West/Middleton WI West 8102 Excelsior Dr, Madison, WI Fully refundableReserve now, pay when you stay CA $100 CA $116 total Nov 10 - Nov 11 includes taxes & fees 8/10 Very Good! (1,059 reviews) Love the pool there, always warm! Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=40004&PinnedHotelID=40004&HadPinnedHotel=true®ionId=3000443084) [See all 345 properties in Paoli](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F11%2F2025&endDate=05%2F11%2F2025®ionId=3000443084) 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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)