Title: Romantic Vacations in Far Southeast Side 2026 | Expedia.ca ![](https://images.trvl-media.com/place/829/b4cf8e95-0f92-4795-af28-19f97bbf7dad.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southeast Side Romantic Vacations ## 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 ## Flight and Romantic hotel deals in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/f931dcd0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eaglewood Resort and Spa CA $557 per person Mar 5 - Mar 9 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.8/10 Excellent! (1,004 reviews) Clean hotel, very friendly staff Reviewed on Dec 9, 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 CA $873 per person Jan 29 - Feb 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Amazing hotel, location, staff, and food!! Reviewed on Dec 8, 2025 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $858 per person Mar 5 - Mar 9 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly. Reviewed on Dec 6, 2025 ![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 $660 per person Jan 23 - Jan 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience. Reviewed on Dec 9, 2025 ![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 $1,307 per person Jan 23 - Jan 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Romantic holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![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 $826 per person Feb 19 - Feb 22 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Amazing hotel, location, staff, and food!! Reviewed on Dec 8, 2025 ![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 $1,307 per person Jan 23 - Jan 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 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 CA $1,183 per person Feb 15 - Feb 18 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,003 reviews) Excellent service throughout the hotel Reviewed on Nov 29, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Romantic holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![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 $660 per person Jan 23 - Jan 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (380 reviews) The rooms were great. Very spacious, fully stocked kitchen and extremely clean. We loved having access to the 8th floor with the steam room, sauna, fitness center, game rooms, and socializing areas 24/7\. Would love to experience it in the summer with the pool and outdoor areas. We were also fortunate enough to attend during their Christmas Brunch buffet which was such a great perk! If the price stays around the same, I will continue to stay at Level hotels exclusively in any cities I visit that has one! I’ve already told so many people about my wonderful hotel experience. Reviewed on Dec 9, 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 CA $873 per person Jan 29 - Feb 1 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,773 reviews) Amazing hotel, location, staff, and food!! Reviewed on Dec 8, 2025 ![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 $1,307 per person Jan 23 - Jan 26 found 2 hours ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,000 reviews) Absolutely fantastic hotel great service, you couldn’t ask for more. Reviewed on Dec 3, 2025 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Romantic holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Eaglewood Resort and Spa](https://images.trvl-media.com/lodging/1000000/900000/897200/897168/f931dcd0_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eaglewood Resort and Spa CA $557 per person Mar 5 - Mar 9 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.8/10 Excellent! (1,004 reviews) Clean hotel, very friendly staff Reviewed on Dec 9, 2025 ![Hilton Chicago O'Hare Airport](https://images.trvl-media.com/lodging/1000000/10000/8100/8058/ce2102d4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Chicago O'Hare Airport O'Hare CA $858 per person Mar 5 - Mar 9 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 8.2/10 Very Good! (2,158 reviews) It’s convenient but old features and breakfast was overpriced. Cheap and simple menus. Service person was not friendly. Reviewed on Dec 6, 2025 ![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 $812 per person Jan 9 - Jan 13 found 1 day ago Roundtrip flight included Toronto (YYZ) 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 Don't see what you're looking for? See all available trips from Columbus to Far Southeast Side [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-10/2026-01-17/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan unforgettable romantic Far Southeast Side vacations #### What are some of the benefits of booking a romantic Far Southeast Side vacation? When booking a romantic Far Southeast 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 Far Southeast 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 Far Southeast 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 $557 and can enjoy savings of up to 27 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 Far Southeast 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 Far Southeast 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 Far Southeast Side. #### Can I book a romantic Far Southeast 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 Far Southeast Side search. #### Can I book a romantic trip to Far Southeast Side that is fully refundable? Several romantic Far Southeast 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 > - [Romantic vacations in Toronto ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178314/Toronto) > - [Romantic vacations in Nova Scotia ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11173/Nova-Scotia) > - [Romantic vacations in Montreal ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178288/Montreal) > - [Romantic vacations in Vancouver ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178315/Vancouver) > - [Romantic vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180017/Quebec) > - [Romantic vacations in the Niagara Falls ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/602721/Niagara-Falls) > - [Romantic vacations in Alberta ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11111/Alberta) > - [Romantic vacations in Victoria ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/1418/Victoria) > - [Romantic vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/8028/Jasper) > - [Romantic vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4332/Banff) > - [Romantic vacations in Ottawa ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178296/Ottawa) > - [Romantic vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/55374/Mont-Tremblant) > - [Romantic vacations in Kingston ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/180034/Kingston) > - [Romantic vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/4115/Whistler) > - [Romantic vacations in Winnipeg ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6141041/Winnipeg) > - [Romantic vacations in Muskoka ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/6343146/Muskoka-District) > - [Romantic vacations in Collingwood ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/11938/Collingwood) > - [Romantic vacations in Calgary ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/178245/Calgary) > - [Romantic vacations in Canada ](https://www.expedia.ca/lp/theme-vacations/romantic-vacations/31/Canada) ## More Vacations Ideas [Flights to Far Southeast Side ](https://expedia.ca/Cheap-Flights-To-Far-Southeast-Side.d553248635976475411.Travel-Guide-Flights)[ Far Southeast Side Hotels ](https://expedia.ca/Far-Southeast-Side-Hotels.d553248635976475411.Travel-Guide-Hotels)[ Far Southeast Side Vacation Rentals ](https://expedia.ca/Far-Southeast-Side-Vacation-Rentals.d553248635976475411.Travel-Guide-VacationRentals)[ Far Southeast Side Car Rentals ](https://expedia.ca/Car-Rentals-In-Far-Southeast-Side.d553248635976475411.Car-Rental-Guide)[ Far Southeast Side Vacations ](https://expedia.ca/Far-Southeast-Side.d553248635976475411.Destination-Travel-Guides) \* 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