Title: Honeymoon Vacations in Far Southeast Side 2025/2026 | Expedia.ca ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southeast Side Honeymoon 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 ## Flight and Honeymoon hotel deals in Far Southeast Side 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 $834 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Not big fan of the room amenities. Reviewed on Oct 14, 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=2463437&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdJNHVaq6kx3jBheXScUEDPdOSsA6o4EXX_MrK-TQTgTS) ![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 $1,038 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 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=982552&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdMNPlLguYFKcx-neHqLXBFLXKXcCIjQY917zDPbt4sXN) ![Arlo Chicago](https://images.trvl-media.com/lodging/27000000/26920000/26910700/26910691/747fff56_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Arlo Chicago Downtown Chicago CA $871 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,826 reviews) excellent hotel, the staff, access to the city. We had a nice time in Chicago Reviewed on Oct 17, 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=26910691&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdJNHVaq6kx3jBheXScUEDPemZveXPYB82Y9rjYLF3ITq) ![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 $950 per person Jan 8 - Jan 12 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-12/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=40&dealMarker=opOYYDLWKgSt1Y7OHaguV07ZBBc1c-AwkeuvxksvkeFA283BGEgwnlwvRfpLXJSP) ![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 $1,034 per person Dec 26 - Jan 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,222 reviews) It was very clean, quiet and a unique space. It was in walking distance of a lot of great restaurants. My husband loved the mattress. Great water pressure on the fourth floor. Reviewed on Oct 17, 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=19381112&paandie=true&HotelClass=40&dealMarker=1Jmr_eciIvxQfm858ExzdMNPlLguYFKcx-neHqLXBFJ8rZuIw9mbqiktIurUKyCV) 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/2025-11-18/2025-11-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Honeymoon 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 $950 per person Jan 8 - Jan 12 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-12/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&HotelClass=50&dealMarker=opOYYDLWKgSt1Y7OHaguV07ZBBc1c-AwkeuvxksvkeFA283BGEgwnlwvRfpLXJSP) ![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 $1,374 per person Jan 8 - Jan 12 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-12/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&HotelClass=50&dealMarker=opOYYDLWKgSt1Y7OHaguVyC1O_-i6stGGsf92vJEpAbvZ7Owz3w6vDZNVtQJIQj-) ![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 $1,363 per person Dec 23 - Dec 27 found 1 day ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-23/2025-12-27/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&HotelClass=50&dealMarker=o-gXl4B8HlDRTTvE1yGYl4E8uDwKUzCjh4XkoKnmRZv5pmopiP_5ieFct1OB3Jfq) 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/2025-11-18/2025-11-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Honeymoon holidays in Far Southeast Side 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 $613 per person Dec 12 - Dec 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (1,011 reviews) Not big fan of the room amenities. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&HotelClass=40&dealMarker=fGBlmbDjOackFL1GOo3VlqAn7hUTB4A29wXn9rTFehqWfNuDgmttTLwjPRsyot6B) ![The Langham, Chicago](https://images.trvl-media.com/lodging/7000000/6310000/6309400/6309326/33b4ff92_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Langham, Chicago Downtown Chicago CA $1,176 per person Nov 26 - Nov 29 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.8/10 Exceptional! (1,005 reviews) Excellent staff, check in process and dining experiences all superb! Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-26/2025-11-29/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6309326&paandie=true&HotelClass=40&dealMarker=PA3FMZb837eT9WkrMtHjEhY9-0fIp6FnffXocxwFJbRTJ0pur4oO9X4h0bojbBg9) ![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 $657 per person Dec 12 - Dec 15 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,085 reviews) Ideal area if it’s your first time visiting Chicago. Hotel staff was very friendly. Reviewed on Oct 16, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-12-12/2025-12-15/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&HotelClass=40&dealMarker=fGBlmbDjOackFL1GOo3VlkvB94mD3VF9zAbN_trAiuIapyl7LRt3eBkRvNPsdj6n) 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/2025-11-18/2025-11-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Honeymoon 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 $950 per person Jan 8 - Jan 12 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Chicago (ORD) 9.4/10 Exceptional! (1,716 reviews) Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel. Reviewed on Oct 15, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-08/2026-01-12/?FromAirport=YVR&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1723215&paandie=true&dealMarker=opOYYDLWKgSt1Y7OHaguV07ZBBc1c-AwkeuvxksvkeFA283BGEgwnlwvRfpLXJSP) ![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 $1,498 per person Nov 24 - Nov 28 just found Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9.4/10 Exceptional! (1,002 reviews) This is a very nice hotel. The staff is super accommodating. The location is one of the best in the area for shopping and dining. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2717582&paandie=true&dealMarker=T5O_T8hQemw9aH9wDC3MZJwDUI9Xp0GneEoMIclPTrHkLAodztSzyvbpJhmXlPH1) ![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 $1,278 per person Nov 24 - Nov 28 just found Roundtrip flight included Calgary (YYC) to Chicago (ORD) 9.6/10 Exceptional! (1,002 reviews) The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better. Reviewed on Oct 14, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-28/?FromAirport=YYC&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=T5O_T8hQemw9aH9wDC3MZJwDUI9Xp0GneEoMIclPTrF2_1Fa5ZwcAlcfP018IeDc) 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/2025-11-18/2025-11-25/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 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) ## 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 ![QR code to download the app](data:image/png;base64,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)