Far Southwest Side Holidays

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Our guide on 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
A coastal cityscape with a marina, dense urban buildings, and a large body of water.

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.

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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.

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Chicago, Illinois, USA Downtown City Skyline from the South Side

Beverly

Beverly is well liked for its restaurants and churches. If you're hoping to see more of the larger area, Martin Luther King Drive and Chicago State University are some interesting sights nearby to check out.

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Washington Heights

2 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.

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Morgan Park

2 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.

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Far Southwest Side Holiday

Our pick of the best Far Southwest Side Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$213
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,283 reviews)
"Stay was fine. I’d love to leave five stars but I have been asking why I was charged an additional 104 usd to my credit card after we left via hotels.com chat and emailing the hotel directly but they have yet to respond. Hoping this gets me a reply and I can update my review"

Reviewed on 10 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$288
30 Aug - 31 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

171 W Randolph St Chicago IL
Fully refundableReserve now, pay when you stay
NZ$415
7 Sept - 8 Sept
includes taxes & fees
The Allegro Royal Sonesta Hotel Chicago Loop
See all 4,633 properties in Far Southwest Side
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.
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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.
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Highland Community Bank

Learn about the local history of Chicago when you take a trip to Highland Community Bank.
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Final Call Newspaper Headquarters

Find out about the history of Chicago when you take a trip to Final Call Newspaper Headquarters.
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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.
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What to do in Far Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$47
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$42
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

NZ$69
per adult
92% of travellers recommend
Art Institute of Chicago
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Frequently asked questions

How much does a Far Southwest Side holiday package cost?
Tailor make your Far Southwest Side holiday package from an affordable . 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.