Title: South Side Vacation Packages 2026 from $554 | Expedia.com [South Side Travel Guide](https://expedia.com/South-Side.dx553248635074842823)[Hotels in South Side](https://expedia.com/South-Side-Hotels.d553248635074842823.Travel-Guide-Hotels)[Vacation Rentals in South Side](https://expedia.com/South-Side-Vacation-Rentals.d553248635074842823.Travel-Guide-VacationRentals)[Flights to South Side](https://expedia.com/Cheap-Flights-To-South-Side.d553248635074842823.Travel-Guide-Flights)[Things to do in South Side](https://expedia.com/Things-To-Do-In-South-Side.d553248635074842823.Travel-Guide-Activities)[Car Rentals in South Side](https://expedia.com/Car-Rentals-In-South-Side.d553248635074842823.Car-Rental-Guide) ![](https://images.trvl-media.com/place/553248635074842823/b2e1e3a5-ccd2-44b6-98c8-396a826d999c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # South Side Vacations from $554 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## The Latest South Side vacation packages 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 Save 100% on your flight $554 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.2/10 Very Good! (2,582 reviews) The property looks beautiful and the staff is very friendly. The details are, however, very lacking. The window in my room was drafty and upon inspection there were stains on the curtains. The shower had basically no edge to it and the curtain was short enough that the floor flooded when we showered. The bed was also not comfortable- especially the pillows which had zero support. It's a good location but I definitely won't be staying here again. Reviewed on Mar 19, 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 Save 100% on your flight $732 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (3,495 reviews) The breakfast was incredibly delicious. The hotel in general is a 10 out of 10. Reviewed on Mar 20, 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 Save 100% on your flight $847 per person May 26 - May 30 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (441 reviews) Spacious room with great views and washer and dryer Reviewed on Mar 17, 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 Save 100% on your flight $676 per person May 22 - May 26 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9/10 Wonderful! (3,314 reviews) The staff was super helpful and very welcoming. The room had an amazing view for us, beings it was our first time being in Chicago. It’s was so close to everything we wanted to visit and super convenient. I will most definitely stay at this hotel again for future stays in the city.!! Thank you so much for taking pride in your establishment, and your employees, as both we’re definitely deserving of a 5 star rating and review.! Reviewed on Mar 17, 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 Save 100% on your flight $722 per person May 15 - May 18 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,401 reviews) Great location, views, & amenities. Reviewed on Mar 20, 2026 Don't see what you're looking for? See all available trips from Columbus to South Side [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-20/2026-04-27/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Where to stay in South Side Find the best South Side areas and neighborhoods for the activities you enjoy most. [Learn more about South Side](https://expedia.com/South-Side.dx553248635074842823) ![Explore exhibits and attractions at Chicago Museum of Science and Industry in Illinois, USA](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Hyde Park 4 out of top 10 points of interest in this area 4.5/5(136 area reviews) Art and history abound in this architecturally impressive and leafy neighborhood between Washington Park and the shores of Lake Michigan. [Find hotel + flight trips in Hyde Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Hyde%20Park&DestID=117842&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![EyeEm Custom Shoots Q4 2018](https://images.trvl-media.com/place/6003647/e3f94976-3603-43a7-a36a-570792654b8d.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Chinatown 4/5(204 area reviews) If you're spending time in Chinatown, you might enjoy attractions like Chinese American Museum of Chicago and On Leong Building. You might also enjoy the neighborhood's ample dining options before hopping on the metro at Cermak-Chinatown Station to see more of the city. [Find hotel + flight trips in Chinatown](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Chinatown&DestID=6003647&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![www.alamy.com](https://images.trvl-media.com/place/6132075/cfd0936f-7a46-4712-9bcf-9fc886479e02.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bridgeport 4/5(1 area review) Well-liked for its restaurants and churches, Bridgeport is worth a visit. Check out the variety of things to see and do like Bridgeport Art Center and Zhou B Art Center, and jump on the metro at Halsted Station (Orange Line) to get around the city. [Find hotel + flight trips in Bridgeport](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bridgeport&DestID=6132075&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Bronzeville Bridge ](https://images.trvl-media.com/place/6132245/bdf0ca23-8e04-4a02-a6f8-aaeeeaf14c16.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Bronzeville 1 out of top 10 points of interest in this area 3.5/5(293 area reviews) Travelers choose Bronzeville for its abundant dining options. Hop aboard the metro at 35th-Bronzeville-IIT Station or Indiana Station and check out top sights like Lake Michigan. [Find hotel + flight trips in Bronzeville](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bronzeville&DestID=6132245&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Aerial Chicago Douglas Neighborhood](https://images.trvl-media.com/place/6132367/ef7d8028-54cc-4a3b-8ea2-51bfd9daba05.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Douglas 1 out of top 10 points of interest in this area Visitors often come to Douglas for its abundant dining options, but many stay to explore sights like Lake Michigan and McCormick Tribune Center. Getting around the area on the metro is easy if you catch a ride at 35th-Bronzeville-IIT Station. [Find hotel + flight trips in Douglas](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Douglas&DestID=6132367&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in South Side ![Aerial View of a large University in the Chicago Neighborhood of Hyde Park](https://images.trvl-media.com/place/6064081/ed547d2b-1357-42b3-840a-f88661f7db9c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### University of Chicago 4.5/5(1,169 reviews) Enjoy the collegiate vibe when you visit University of Chicago, during your travels in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area. [](https://expedia.com/University-Of-Chicago-Hyde-Park.d6064081.Vacation-Attraction) ![Explore exhibits and attractions at Chicago Museum of Science and Industry in Illinois, USA](https://images.trvl-media.com/place/6064043/29f0986c-b49b-485b-8fcc-9b5424ca802f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Griffin Museum of Science and Industry 4.5/5(1,385 reviews) This large, interactive museum contains a coal mine and World War II submarine among its many attractions. [](https://expedia.com/Griffin-Museum-Of-Science-And-Industry-Hyde-Park.d6064043.Vacation-Attraction) ![Chicago El Train at The Illinois Institute of Technology](https://images.trvl-media.com/place/6168375/c9c60c06-88be-4634-b3e8-e9900fa27e8f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Illinois Institute of Technology 3.5/5(4 reviews) Walk around the campus at Illinois Institute of Technology during your visit to Chicago. Experience the fascinating museums and acclaimed art scene in this vibrant area. [](https://expedia.com/Illinois-Institute-Of-Technology-Douglas.d6168375.Vacation-Attraction) ### What to do in South Side ![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 360 CHICAGO Observation Deck $26 per adult **86%** of travellers recommend [](https://expedia.com/things-to-do/360-chicago-observation-deck.a170348.activity-details) ![Skydeck - Willis Tower Admission ](https://mediaim.expedia.com/localexpert/1342523/52299998-0f25-4483-b147-6aa89e72ca8e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skydeck - Willis Tower Admission $44 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/skydeck-willis-tower-admission.a1342523.activity-details) ![Chicago Bulls Basketball Game at United Center](https://mediaim.expedia.com/localexpert/47300776/972792e4-c31c-4347-9c2d-8d50ffbad913.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Chicago Bulls Basketball Game at United Center $61 per adult **80%** of travellers recommend [](https://expedia.com/things-to-do/chicago-bulls-basketball-game-at-united-center.a47300776.activity-details) [See all activities in South Side](https://expedia.com/things-to-do/search?rid=553248635074842823) ## South Side Hotel Deals ![Holiday Inn Chicago – Midway Airport S by IHG](https://images.trvl-media.com/lodging/1000000/10000/2200/2190/d5acb403_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Chicago – Midway Airport S by IHG 7353 S Cicero Avenue Chicago IL Fully refundable $124 nightly $144 total Apr 5 - Apr 6 Total with taxes and fees 8.4/10 Very Good! (1,003 reviews) Fast, friendly, outstanding service Reviewed on Mar 18, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F5%2F2026&endDate=4%2F6%2F2026&selected=2190&PinnedHotelID=2190&HadPinnedHotel=true®ionId=553248635074842823) ![Jaslin Hotel](https://images.trvl-media.com/lodging/14000000/13330000/13320300/13320264/90849841_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Jaslin Hotel 261 West Cermak Rd Chicago IL Fully refundableReserve now, pay when you stay $104 nightly $123 total Apr 1 - Apr 2 Total with taxes and fees 8.8/10 Excellent! (1,184 reviews) When I first got to the hotel to see if there was an early check in had to wait 15 mins at the front desk for someone to help. My room did not get cleaned and nothing got restocked I stayed there for 2 nights. There was a chair in the room that had a broken leg which was concerning. Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=13320264&PinnedHotelID=13320264&HadPinnedHotel=true®ionId=553248635074842823) ![SpringHill Suites by Marriott Chicago Chinatown](https://images.trvl-media.com/lodging/65000000/64630000/64624400/64624399/575b0923_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SpringHill Suites by Marriott Chicago Chinatown 2357 S WENTWORTH AVE Chicago IL Fully refundableReserve now, pay when you stay $129 nightly $151 total Mar 24 - Mar 25 Total with taxes and fees 9.6/10 Exceptional! (1,002 reviews) Clean Reviewed on Mar 16, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=64624399&PinnedHotelID=64624399&HadPinnedHotel=true®ionId=553248635074842823) [See all 463 properties in South Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F21%2F2026&endDate=3%2F22%2F2026®ionId=553248635074842823) 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. ## Find the Best South Side Vacation Packages ## South Side Essential Information | Language | English | | --------------- | -------------------------- | | Currency | U.S dollars | | Closest Airport | O'Hare Intl. Airport (ORD) | ## 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.com/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.com/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) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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