Title: Southwest Side Vacation Packages 2026 from $295 | Expedia.com [Southwest Side Travel Guide](https://expedia.com/Southwest-Side.dx553248635976475403)[Hotels in Southwest Side](https://expedia.com/Southwest-Side-Hotels.d553248635976475403.Travel-Guide-Hotels)[Vacation Rentals in Southwest Side](https://expedia.com/Southwest-Side-Vacation-Rentals.d553248635976475403.Travel-Guide-VacationRentals)[Flights to Southwest Side](https://expedia.com/Cheap-Flights-To-Southwest-Side.d553248635976475403.Travel-Guide-Flights)[Car Rentals in Southwest Side](https://expedia.com/Car-Rentals-In-Southwest-Side.d553248635976475403.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Southwest Side Vacations from $295 ## 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 Southwest Side vacation packages Price found within the past 48 hours. Click for updated prices. ![Eurostars Magnificent Mile](https://images.trvl-media.com/lodging/2000000/1890000/1880400/1880320/08bbf982_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Eurostars Magnificent Mile Downtown Chicago Save 100% on your flight $295 per person Apr 9 - Apr 12 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 8.8/10 Excellent! (3,098 reviews) Room was gorgeous, felt very luxurious for the price! Front desk staff was great at check out! Reviewed on Feb 26, 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 $684 per person May 20 - May 25 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Great breakfast and friendly staff Reviewed on Feb 28, 2026 ![JW Marriott Chicago](https://images.trvl-media.com/lodging/4000000/3540000/3538400/3538327/232aa080_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JW Marriott Chicago Downtown Chicago Save 100% on your flight $404 per person May 1 - May 3 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.2/10 Wonderful! (1,000 reviews) The room was great and clean , there was a toilet issue but the staff members gladly were readily available to fix it all ! The amenities including the hot tub, and pool as well as the in room service breakfast was 5/5 . Would absolutely stay here again . Reviewed on Feb 17, 2026 ![La Banque Hotel](https://images.trvl-media.com/lodging/15000000/14710000/14702200/14702161/a8c9af9e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Banque Hotel Save 100% on your flight $347 per person Apr 25 - Apr 28 found 1 hour ago Roundtrip flight included New York (NYC) to Chicago (ORD) 9.4/10 Exceptional! (447 reviews) Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring. Reviewed on Jan 26, 2026 ![Bridgeview Inn Chicago Area](https://images.trvl-media.com/lodging/92000000/91910000/91900800/91900710/6980505e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bridgeview Inn Chicago Area Save 100% on your flight $415 per person May 19 - May 25 found 8 hours ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 6.4/10 (105 reviews) Newly remodeled room. Reviewed on Oct 11, 2025 Don't see what you're looking for? See all available trips from Columbus to Southwest Side [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-04-01/2026-04-08/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CHI&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_553248635976475403) ## Where to stay in Southwest Side Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. [Learn more about Southwest Side](https://expedia.com/Southwest-Side.dx553248635976475403) ![artist paints mural on a city street](https://images.trvl-media.com/place/553248635976382392/344cd423-407b-410b-8a97-509979ed4de1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Back of the Yards 2 out of top 10 points of interest in this area While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center. [Find hotel + flight trips in Back of the Yards](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Back%20of%20the%20Yards&DestID=553248635976382392&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago, IL showing interior views, heritage elements and an airport](https://images.trvl-media.com/place/5719117/ef1b962b-07e6-469b-abf5-73ab99ceb6ee.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Garfield Ridge 3/5(9 area reviews) Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area. [Find hotel + flight trips in Garfield Ridge](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Garfield%20Ridge&DestID=6132357&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Northbrook village landscape, is an affluent suburb of Chicago, located at the northern edge of Cook County, Illinois, United States.](https://images.trvl-media.com/place/6132389/77289410-b98d-494e-8ca3-cc13ffbac29b.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### McKinley Park 1 out of top 10 points of interest in this area Be sure to check out the monuments and shopping while you're strolling through McKinley Park, and hop on the metro at 35th-Archer Station to see more of the surrounding area. [Find hotel + flight trips in McKinley Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=McKinley%20Park&DestID=6132389&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Fall landscape at Starved Rock.](https://images.trvl-media.com/place/6132396/f68d1de3-a801-4f54-9299-5e010c68c53f.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Brighton Park The restaurants and shopping are a few reasons travelers visit Brighton Park. Though there aren't many top sights in the neighborhood, you can visit United Center and Bridgeport Art Center, a few notable attractions nearby. [Find hotel + flight trips in Brighton Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Brighton%20Park&DestID=6132396&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Chicago Skyline viewed from South Pond in Lincoln Park](https://images.trvl-media.com/place/101911/20842d88-22a0-424e-9f11-57b3582fa12a.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Englewood 1 out of top 10 points of interest in this area While you're strolling through Englewood, you may want to check out the beaches and restaurants. If you want to see more of the area, hop on the metro at Halsted Station or 63rd Station. [Find hotel + flight trips in Englewood](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Englewood&DestID=101911&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Southwest Side ![Wrigley Field featuring cbd, a sporting event and a city](https://images.trvl-media.com/place/6034754/d10ea4fa-9a61-425f-b749-3325e9303223.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Wrigley Field 4.5/5(2,128 reviews) Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium. [](https://expedia.com/Wrigley-Field-Lakeview.d6034754.Vacation-Attraction) ![Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept](https://images.trvl-media.com/place/6156167/9a44be22-322b-4187-8844-e2aa99b46184.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Michigan Avenue 4.5/5(332 reviews) You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants. [](https://expedia.com/Michigan-Avenue-Downtown-Chicago.d6156167.Vacation-Attraction) ![Navy Pier featuring a sunset and rides](https://images.trvl-media.com/place/6069215/a6173fc5-04f4-4a58-b70a-61c78e1b648e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Navy Pier 4.5/5(4,870 reviews) A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district. [](https://expedia.com/Navy-Pier-Downtown-Chicago.d6069215.Vacation-Attraction) ### What to do in Southwest Side ![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) ![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Flyover in Chicago $38 per adult **98%** of travellers recommend [](https://expedia.com/things-to-do/flyover-in-chicago.a50023979.activity-details) [See all activities in Southwest Side](https://expedia.com/things-to-do/search?rid=553248635976475403) ## Southwest Side Hotel Deals ![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Congress Plaza Hotel 520 South Michigan Avenue Chicago IL Fully refundableReserve now, pay when you stay $101 nightly $118 total Mar 2 - Mar 3 Total with taxes and fees 8/10 Very Good! (9,895 reviews) We mainly go to Chicago for medical appointments and it is \*so awesome\* that you can actually open the windows here.That is the main reason we chose it. Because Dad has cancer we aired it out and then ran our own air purifier. No bad smells or anything, we're just being cautious because of his health. ... Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F2%2F2026&endDate=3%2F3%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=553248635976475403) ![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Riu Plaza Chicago 150 East Ontario Street Chicago IL Fully refundableReserve now, pay when you stay $137 nightly $161 total Mar 4 - Mar 5 Total with taxes and fees 9.4/10 Exceptional! (3,428 reviews) Great breakfast and friendly staff Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F4%2F2026&endDate=3%2F5%2F2026&selected=102622712&PinnedHotelID=102622712&HadPinnedHotel=true®ionId=553248635976475403) ![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Chicago Downtown River North 600 N State St Chicago IL Fully refundableReserve now, pay when you stay $110 nightly $130 total Mar 5 - Mar 6 Total with taxes and fees 8.6/10 Excellent! (5,696 reviews) Great room, great breakfast Reviewed on Feb 28, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=553248635976475403) [See all 5,179 properties in Southwest Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026®ionId=553248635976475403) 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 Southwest Side Vacation Packages ## Southwest 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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