Far Southwest Side Vacation Packages
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Top Far Southwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
CA $1,192
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)
This place was 10/10. The room was extremely clean. Had everything you needed. Even a washer and dryer. The staff were very helpful and friendly. They have a cute children’s area. The amenities floor was amazing and comfortable. Great area to walk to dinning and shopping and the oak st beach. We are walkers so while nothing was right around the corner we could walk to many sights like the river walk, the bean, chicago 360, all the stores.
Reviewed on Sep 17, 2026
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
Morgan Park
1 out of top 10 points of interest in this area
Travelers enjoy Morgan Park for its restaurants and shopping. Consider checking out Beverly Arts Center while you're in the area.
Ashburn
The restaurants and churches are just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Childrens Museum of Oak Lawn and Wintrust Sports Complex are a few top places to visit.
Beverly
The restaurants and churches are just a few features travelers like about Beverly. If you want to do some sightseeing nearby, Beverly Arts Center and Childrens Museum of Oak Lawn are a few top places to visit.
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
Appreciated for its restaurants and shopping, you might consider exploring Washington Heights. Check out the variety of things to see and do like Carter G. Woodson Library, and jump on the metro at 95th Street - Longwood Station or 103rd Street Washington Heights Station to get around the city.
Ready to book your vacation to Far Southwest Side?
Far Southwest Side Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
CA $255
per night
Sep 27 - Sep 28
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $225
per night
Sep 27 - Sep 28
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $222
per night
Sep 27 - Sep 28
8/10 Very good! (10,270 reviews)
"Grand old hotel. Worth seeing … but getting old."
Reviewed on Sep 17, 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.
Highland Community Bank
Learn about the local history of Chicago when you take a trip to Highland Community Bank.
Final Call Newspaper Headquarters
Find out about the history of Chicago with a stop at Final Call Newspaper Headquarters.
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
CA $34
per adult
90% of travellers recommend
Frequently asked questions
How much does a Far Southwest Side vacation package cost?
Tailor make your Far Southwest Side vacation package from an affordable CA $655. 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 vacation 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 vacation?
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 favorite 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 vacation package lets you organize 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 vacation package?
With a vacation 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 vacation package?
If your vacation 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
