Title: Far Southwest Side Vacation Packages 2026 from $297 | Expedia.com [Far Southwest Side Travel Guide](https://expedia.com/Far-Southwest-Side.dx553248635976475353)[Hotels in Far Southwest Side](https://expedia.com/Far-Southwest-Side-Hotels.d553248635976475353.Travel-Guide-Hotels)[Vacation Rentals in Far Southwest Side](https://expedia.com/Far-Southwest-Side-Vacation-Rentals.d553248635976475353.Travel-Guide-VacationRentals)[Flights to Far Southwest Side](https://expedia.com/Cheap-Flights-To-Far-Southwest-Side.d553248635976475353.Travel-Guide-Flights)[Car Rentals in Far Southwest Side](https://expedia.com/Car-Rentals-In-Far-Southwest-Side.d553248635976475353.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Far Southwest Side Vacations from $297 ## 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 Far Southwest Side vacation packages Price found within the past 48 hours. Click for updated prices. ![Illinois Beach Hotel](https://images.trvl-media.com/lodging/84000000/83570000/83567200/83567194/45a93a6e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Illinois Beach Hotel Save 100% on your flight $297 per person May 14 - May 18 found 22 hours ago Roundtrip flight included New York (LGA) to Chicago (ORD) 8/10 Very Good! (478 reviews) Was an wonderful experience. The staff was very kind and helpful. The view was amazing. Highly recommend any time of the year! Reviewed on Jan 12, 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 $480 per person May 5 - May 8 found 1 day ago Roundtrip flight included Atlanta (ATL) to Chicago (ORD) 9.4/10 Exceptional! (2,790 reviews) Clean amenities, amazing food, and great service! Reviewed on Feb 27, 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 $541 per person Apr 30 - 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 $388 per person May 25 - May 28 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) 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 ![Blue Chip Casino Hotel and Spa](https://images.trvl-media.com/lodging/3000000/3000000/2991300/2991209/21bfd0c8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Blue Chip Casino Hotel and Spa Save 100% on your flight $342 per person Apr 18 - Apr 23 found 1 day ago Roundtrip flight included Dallas (DFW) to Chicago (ORD) 8.2/10 Very Good! (1,817 reviews) Clean, friendly staff, fun time Reviewed on Feb 25, 2026 Don't see what you're looking for? See all available trips from Columbus to Far Southwest Side [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-28/2026-04-04/?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_553248635976475353) ## Where to stay in Far Southwest Side Find the best Far Southwest Side areas and neighborhoods for the activities you enjoy most. [Learn more about Far Southwest Side](https://expedia.com/Far-Southwest-Side.dx553248635976475353) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Beverly The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Carter G. Woodson Library and Martin Luther King Drive are a few top places to visit. [Find hotel + flight trips in Beverly](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Beverly&DestID=6132394&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Ashburn The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Chicago Ridge Shopping Mall and Childrens Museum of Oak Lawn are a few top places to visit. [Find hotel + flight trips in Ashburn](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Ashburn&DestID=6132369&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Auburn Gresham 2 out of top 10 points of interest in this area While visiting Auburn Gresham, you might make a stop by sights like Highland Community Bank and Final Call Newspaper Headquarters. [Find hotel + flight trips in Auburn Gresham](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Auburn%20Gresham&DestID=553248635976386802&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Washington Heights 2 out of top 10 points of interest in this area The restaurants and shopping are just a few things visitors like about Washington Heights. Carter G. Woodson Library and Dr. Percy Julian Residence are worthwhile spots to check out, and you can hop on the metro at 95th Street - Longwood Station or 103rd Street Washington Heights Station to get around the larger area. [Find hotel + flight trips in Washington Heights](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Washington%20Heights&DestID=6132290&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ![Default Image](https://images.trvl-media.com/media/content/expus/graphics/deals/TE_Clouds_card_r1.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Morgan Park 1 out of top 10 points of interest in this area The restaurants and shopping are just a few features travelers like about Morgan Park. If you want to do some sightseeing nearby, Pullman Historic District and A. Philip Randolph Pullman Porter Museum are a few top places to visit. [Find hotel + flight trips in Morgan Park](https://expedia.com/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Morgan%20Park&DestID=6132289&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods) ### Discover the most popular places to visit in Far 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 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 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 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 Far 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 Far Southwest Side](https://expedia.com/things-to-do/search?rid=553248635976475353) ## Far 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 1 - Mar 2 Total with taxes and fees 8/10 Very Good! (9,894 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%2F1%2F2026&endDate=3%2F2%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true®ionId=553248635976475353) ![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! (3,423 reviews) Tudo impecável 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=553248635976475353) ![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! (5,692 reviews) Hotel is beautiful and located in the heart of everything. Starbucks outside is a plus. Breakfast is excellent and rooms are spacious. Wish they have a whirlpool Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true®ionId=553248635976475353) [See all 4,887 properties in Far Southwest Side](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F1%2F2026&endDate=3%2F2%2F2026®ionId=553248635976475353) 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 Far Southwest Side Vacation Packages ## Far 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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