Far Southwest Side Holidays
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Top Flight + Hotel Deals in Far Southwest Side
Price found within the past 48 hours. Click for updated prices.
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
Ashburn
The restaurants and churches are a few reasons travellers visit Ashburn. Though there aren't many top sights in the neighbourhood, you can visit Wintrust Sports Complex and Chicago Ridge Shopping Mall, a few notable attractions nearby.
Beverly
Beverly is well liked for its restaurants and churches. If you're hoping to see more of the larger area, Beverly Arts Center and Harborside International Golf Center are some interesting sights nearby to check out.
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.
Washington Heights
1 out of top 10 points of interest in this area
Washington Heights is well liked for its restaurants and shopping. If you're hoping to get in some sightseeing, Carter G. Woodson Library and Dr. Percy Julian Residence are top spots, and you can jump on the metro at 95th Street - Longwood Station or 103rd Street Washington Heights Station to get around.
Morgan Park
1 out of top 10 points of interest in this area
Visitors to Morgan Park like its restaurants and shopping, and Beverly Arts Center is a sight worth a stop.
Top hotels in Far Southwest Side
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,243 reviews)
"Beautiful building. Clean room and fairly spacious. Bed wasn't super comfortable but it was fine for 2 night stay. The elevators were fast and we had a small view of the lake and Michigan Ave. Super convenient location with lots of food choices within short walk. Easy walk to museum center and Soldier ..."
Reviewed on 1 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€147
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (2,145 reviews)
"Keys"
Reviewed on 1 Sept 2026
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.
Stay near popular Far Southwest Side attractions
Beverly Arts Center
Beverly Arts Center is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Make some time to visit the shops while you're in the area.
Dr. Percy Julian Residence
Find out about the history of Chicago when you spend time at Dr. Percy Julian Residence. Make some time to visit the shops while you're in the area.
Final Call Newspaper Headquarters
Find out about the history of Chicago when you take a trip to Final Call Newspaper Headquarters.
Highland Community Bank
Learn about the local history of Chicago when you take a trip to Highland Community Bank.
Carter G. Woodson Library
You can enjoy some culture when you stop by Carter G. Woodson Library in Chicago. Make some time to visit the shops while you're in the area.
What to do in Far Southwest Side
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
90% of travellers recommend
Frequently asked questions
How much does a Far Southwest Side holiday package cost?
Tailor make your Far Southwest Side holiday package from an affordable €1,247. Choose from any combination of rental cars, flights and hotels to craft the getaway you've been dreaming about. Remember to add on some activities and experiences!
How do I get a cheap travel package to Far Southwest Side?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you a nice amount too. A Far Southwest Side holiday package makes it a cinch to create your dream adventure. With more than 550 airlines all over the world to choose from, finding convenient flights that fit your schedule will be no sweat. On top of that, we have over 1,000,000 hotel options globally to pick from. Now that's what you call choice. Whatever your budget, Expedia can show you the world.
What are the top hotels in Far Southwest Side?
Check out the deals at Congress Plaza Hotel and LondonHouse Chicago, Curio Collection by Hilton in Chester Highlands. Any good Far Southwest Side itinerary has to include a stop in this great city!
How far in advance should I book my Far Southwest Side holiday?
It can be hard to know when is the perfect time to book your Far Southwest Side trip. But typically the earlier you book, the more affordable the prices. In some cases, you can reserve your flights and hotels nearly a year prior to departure. If you're considering a last-minute getaway, no need to panic! There are incredible bargains posted on Expedia every single day.
What does an Expedia Far Southwest Side travel package include?
Flights, hotels and car rentals — we connect you to the best deals. All you'll have to do is select your favourite combination. Once you've made your booking, you can add on the fun stuff like day tours and sightseeing activities. Our travel packages make it easy to customize an awesome Far Southwest Side trip.
What should I know before booking a Far Southwest Side travel package?
Whether it's relaxation or adventure you're chasing, a Far Southwest Side holiday package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Far Southwest Side Expedia holiday package?
With a holiday package, you're the one in charge. Whether you want to fly to Far Southwest Side in business or coach, simply pick from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Far Southwest Side holiday package?
If your holiday plans in Far Southwest Side have been upended, it's good to know that it is possible to cancel your booking. If you booked less than 24 hours ago, you may be eligible to receive a refund. If your booking is older than that, your airline, hotel or car rental company may charge a fee. For more details, check our Customer Service Portal.
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- Aon Center
- Art Institute of Chicago
- Berwyn Holidays
- Buckingham Fountain
- Canalport Riverwalk Park
- Chicago Board of Trade Building
- Visit Calumet Heights
- Visit Canaryville
- Visit Grand Boulevard
- Chicago Museum Campus Holidays
- Chicago Place Mall
- Visit Pullman
- Visit Roseland
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- Visit West Pullman
- Chicago Holidays
- Cloud Gate
- Credit Union 1 Arena
- Crown Fountain
- Daley Plaza
- Garfield Park Conservatory
- Grant Park
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- Hyde Park Hair Salon
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- Lake Meadows Park
- Michigan Avenue
- Navy Pier
- Visit Oak Lawn
- Prentice Women's Hospital
- Riverdale Holidays
- Visit Riverdale
- Robie House
- Second Franklin Building
- University of Illinois Chicago
- Water Tower Place
- Willis Tower
- Wrigley Building
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
