Title: Pet-friendly 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 Pet-friendly 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 Pet-friendly hotel deals in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Felix River North/Magnificent Mile Downtown Chicago CA $658 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!! Reviewed on Mar 29, 2026 ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $817 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best breakfast buffet I’ve ever had while in Chicago. ALL staff was nice, welcoming and willing to be of assistance. Definitely plan on staying again the next time I’m in Chicago‼️ Reviewed on Mar 29, 2026 ![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,109 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Thank you for your exceptional hospitality Reviewed on Mar 29, 2026 ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/8076f539_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago CA $799 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) Great location. The staff was nice. It was everything we needed. Reviewed on Mar 29, 2026 ![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Saint Clair- Magnificent Mile Downtown Chicago CA $792 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 8.4/10 Very Good! (1,862 reviews) This was perfect for a night in the city! Great all around and will stay again. Great staff at check-in! Reviewed on Mar 27, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Pet-friendly 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/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Trump International Hotel & Tower Chicago Downtown Chicago CA $1,109 per person Jun 19 - Jun 21 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (1,852 reviews) Thank you for your exceptional hospitality Reviewed on Mar 29, 2026 ![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c8149674_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Park Hyatt Chicago Downtown Chicago CA $3,796 per person Jun 3 - Jun 8 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.6/10 Exceptional! (1,004 reviews) Room clean , large comfoy Reviewed on Mar 15, 2026 ![The Ritz-Carlton, Chicago](https://images.trvl-media.com/lodging/1000000/20000/14500/14447/29a217ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ritz-Carlton, Chicago Downtown Chicago CA $1,418 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Chicago (ORD) 9.2/10 Wonderful! (1,001 reviews) The pool was a little tight and dated. The spa overall felt a little dated. The fitness area was fabulous. Reviewed on Mar 22, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Pet-friendly holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Riu Plaza Chicago Downtown Chicago CA $802 per person May 19 - May 22 found 1 day ago Roundtrip flight included Toronto (YTO) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) Best breakfast buffet I’ve ever had while in Chicago. ALL staff was nice, welcoming and willing to be of assistance. Definitely plan on staying again the next time I’m in Chicago‼️ Reviewed on Mar 29, 2026 ![Sable at Navy Pier Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/58000000/57660000/57651200/57651125/6c1738b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sable at Navy Pier Chicago, Curio Collection by Hilton Downtown Chicago CA $1,177 per person Jun 19 - Jun 22 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Amazing experience will be back soon Reviewed on Mar 29, 2026 ![Level Chicago Fulton Market](https://images.trvl-media.com/lodging/96000000/95830000/95823700/95823687/989904ac_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago Fulton Market Downtown Chicago CA $1,178 per person Jun 20 - Jun 23 found 3 hours ago Roundtrip non-stop flight included Montreal (YUL) to Chicago (ORD) 9.2/10 Wonderful! (421 reviews) 10/10 makes you feel at home. One of the best hotels I’ve ever stayed in. Reviewed on Mar 23, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Pet-friendly holidays in Far Southeast Side Price found within the past 48 hours. Click for updated prices. ![Kinzie Hotel](https://images.trvl-media.com/lodging/1000000/1000000/992500/992500/6044b661_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kinzie Hotel Downtown Chicago CA $1,174 per person May 21 - May 25 found 5 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 9.2/10 Wonderful! (2,091 reviews) The staff was really great and the room was fine, nothing exceptional but nothing bad. The walls were thin and we when our neighbors pulled up their shades it was so loud it woke us up. We got a call at 7a with nobody on the other end, that also woke us up. haha Reviewed on Mar 29, 2026 ![Level Chicago – Old Town](https://images.trvl-media.com/lodging/40000000/39810000/39805900/39805843/8c061e2a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Level Chicago – Old Town Downtown Chicago CA $1,346 per person Apr 30 - May 4 found 10 hours ago Roundtrip non-stop flight included Calgary (YYC) to Chicago (ORD) 9/10 Wonderful! (441 reviews) The rooms are extremely clean and have everything you need. The staff is so accommodating and friendly. The view is amazing Reviewed on Mar 27, 2026 ![The Chicago Hotel Collection - Wrigleyville](https://images.trvl-media.com/lodging/24000000/23610000/23604900/23604891/441ad9d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Chicago Hotel Collection - Wrigleyville Lakeview CA $1,385 per person May 21 - May 25 found 5 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Chicago (ORD) 7/10 Good! (974 reviews) Excellent location. Clean rooms Reviewed on Mar 24, 2026 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/2026-04-30/2026-05-07/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Pet-friendly Hotels in Far Southeast Side ![Admiral Motel By Oyo Chicago I-94](https://images.trvl-media.com/lodging/113000000/112490000/112484100/112484089/cdb6bc21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Admiral Motel By Oyo Chicago I-94 9118 S Cottage Grove Ave Chicago IL - 19 min walk from Abbott Park Stay at this hotel in Chicago. Enjoy free parking, room service, and a 24-hour front desk. Popular attractions Griffin Museum of Science and Industry and Jackson ... [](https://expedia.ca/Chicago-Hotels-Admiral-Motel-By-Oyo-Chicago-I-94.h112484089.Hotel-Information) ![4/20 Friendly 12PM Check Out 1 Bedroom Basement](https://images.trvl-media.com/lodging/124000000/123230000/123225500/123225487/0a35506e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 4/20 Friendly 12PM Check Out 1 Bedroom Basement Chicago IL - 5 min drive from Abbott Park Stay at this vacation home in Chicago. Popular attractions Griffin Museum of Science and Industry and Jackson Park are located nearby. 10/10 Exceptional! (1 review) Perfect for parties love every thing about it Reviewed on Mar 14, 2026 [](https://expedia.ca/Chicago-Hotels-420-Friendly-12PM-Check-Out-1-Bedroom-Basement.h123225487.Hotel-Information) ![ Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum ](https://images.trvl-media.com/lodging/100000000/99700000/99692300/99692300/dfe91bbb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Charming 5 bedrooms 2 bath near Downtown Loop and Mc cormick Place, Museum Chicago IL - 6 min drive from Abbott Park Stay at this vacation home in Chicago. Enjoy a garden, laundry facilities, and patios. Popular attractions Griffin Museum of Science and Industry and Jackson ... [](https://expedia.ca/Chicago-Hotels-Charming-5-Bedrooms-2-Bath-Near-Downtown-Loop-And-Mc-Cormick-Place.h99692300.Hotel-Information) [See all 4,604 properties in Far Southeast Side](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635976475411) 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. ## 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.