Title: Romantic Vacations in West Side 2025/2026 | Expedia.ca ![](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # West Side Romantic Vacations ## Book a Hotel + Flight or Car together to unlock savings Stay added Flight added Car - Economy - Premium economy - Business class - First class Leaving from Going to Dates Travellers ## Room 1 Adults ChildrenAges 2 to 17 InfantsYounger than 2 I only need accommodation for part of my trip - ## 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 ## 4 Night Romantic holidays in West Side Price found within the past 48 hours. Click for updated prices. ![Hilton Orrington / Evanston](https://images.trvl-media.com/lodging/1000000/20000/19800/19722/fbf21c1c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Orrington / Evanston Downtown Evanston CA $694 per person Nov 5 - Nov 9 found 2 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 7.6/10 Good! (1,007 reviews) Two mornings received poor service at breakfast. King bed in room. Could not open cabinet Reviewed on Sep 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-09/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19722&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12E76dhwANxHfCxdj6RmZgvBw204EGjBhe8QMzgPBoc5e) ![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 $1,285 per person Dec 27 - Dec 31 found 1 day ago Roundtrip flight included Toronto (YYZ) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent all around Reviewed on Oct 4, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-27/2025-12-31/?FromAirport=YYZ&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=kuh6x8aX6i0Y6IGj3hwLIY_L6ixpMKUysHQB8JUf1ApHQMf0ToIFK-1ku1it8UdW) ![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 CA $2,355 per person Nov 5 - Nov 9 found 2 hours ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.8/10 Exceptional! (1,006 reviews) Excellent hotel, my only complaint would be the Peninsula food service. We ate at the Shanghai Terrace our first night on site and honestly the food was only 2 stars. Specifically the appetizers were minuscule, and 90% pastry dough. Whatever filling was supposed to be inside all the dough largely wasn’t. The whole Peking duck was arranged haphazardly on the plate, the skin was not really crispy, and the taste experience was completely lackluster. As to the main dining room the service continues, as always, to be erratic and frequently slow. Food is sometimes served hot, sometimes not. The room service on our checkout day was absolutely abysmal. We both ordered eggs Benedict and both orders were served not a degree above room temperature. The hollandaise sauce was so cold it had solidified. There really is no excuse for this. And unfortunately we did not have time to return the order as we had a plane to catch and we were running a bit behind. For an otherwise professional hotel the food service and quality is sadly lacking. It leads one to believe that the F&B manager could be a nephew, a cousin, or some other family member need of a job. Reviewed on Sep 27, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-05/2025-11-09/?FromAirport=YHM&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=581213&paandie=true&dealMarker=v-7qfSU6EOWLM_kTp7q12OEP_ZlB7GJDjLQeJOXx9X3vF7qzgCD4uRbNZjYVpiTG) Don't see what you're looking for? See all available trips from Columbus to West Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2025-11-06/2025-11-13/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic West Side vacations #### What are some of the benefits of booking a romantic West Side vacation? When booking a romantic West Side vacation, you'll find quite a few options to make the experience with your partner absolutely unforgettable. Luxury amenities like hot tubs and spa facilities are prominent, but a lot of romantic vacation getaways also make it easy to explore some of the best spots in Chicago. #### How can I find the best vacation packages for couples? If you're looking for a romantic vacation getaway, all you have to do is implement the romantic search filter. That will automatically remove any property that isn't suitable for couples. Just put in your travel dates and the West Side destination, and you'll be met with an array of options for you and your partner to enjoy. #### Can I find cheap romantic vacations for 2 in West Side? Yes, there are several options for booking cheap romantic vacations that don't break the bank. You'll find prices as low as CA $694 and can enjoy savings of up to 29 when you book your hotel and flight together. Budget and luxury options are both available along with everything in between. Sorting your results by price will allow you to view the cheapest options first. #### What do I need to consider when booking a romantic getaway in West Side? Romantic vacation getaways succeed based on catering to what you and your partner specifically want to do. Think about what your partner enjoys and what you want to do as a couple, then opt for something that is especially geared toward fulfilling your ideal romantic vacation getaway experience. Search filters for amenities and proximity to certain attractions throughout West Side certainly come in handy here. #### What amenities should I look for in a luxury romantic vacation? If you and your partner are interested in luxury, you won't have to look far for a romantic vacation getaway that fits. In luxury accommodations, you can enjoy amenities like room service and a hot tub. Some accommodations may even have their own spa facilities complete with massage services that will add an extra touch of romance to your excursion to West Side. #### Can I book a romantic West Side vacation with a hot tub? Yes, and it's easy when you take advantage of available search filters. All you have to do is implement the hot tub filter from the amenities section into your search. This will automatically remove any stays from your search results that do not have hot tubs in them. #### How can I find romantic vacation getaways that are all-inclusive? An all-inclusive trip allows you to plan out your romantic vacation getaway in advance, letting you get a solid number on cost and a full itinerary before you set out. To start this kind of planning, simply apply the filter for all-inclusive trips in your West Side search. #### Can I book a romantic trip to West Side that is fully refundable? Several romantic West Side vacations come with fully refundable reservations. You can filter for this specifically, but every accommodation will list its policy for cancellation in their policy section, which is visible after clicking on a search result. Always make sure to check their policy to determine the requirements. #### Why should I book a romantic vacation with Expedia? Booking your trip with Expedia makes the entire planning process that much easier, as we're your convenient, all-in-one stop for all your travel needs. You can book your stay and your flight, with special discounts potentially available for booking together. Additionally, you can enjoy more discounts by becoming an Expedia Rewards member and getting points to put toward your next booking. Becoming a member is free, so don't hesitate to take advantage. ## More vacations 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 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) ### Top Romantic Vacation Destinations > - 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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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)