Far Southwest Side Vacations from $645

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The Latest Far Southwest Side vacation packages

Price found within the past 48 hours. Click for updated prices.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

Save 100% on your flight

$645

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.4/10 Very Good! (2,128 reviews)

The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.

Reviewed on Aug 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$795

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$745

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$709

per person

Oct 28 - Nov 3

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (157 reviews)

Beautiful room. Great location. Will be back.

Reviewed on Aug 22, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$970

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (2,638 reviews)

I absolutely loved my stay. It was in the perfect location. Walking distance to every site to see. Their customer customer service was great. As well as the in house dining. I definitely will stay here again the next time I visit Chicago

Reviewed on Aug 22, 2026

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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 just a few features travelers like about Ashburn. If you want to do some sightseeing nearby, Wintrust Sports Complex and Chicago Ridge Shopping Mall 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.

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

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 Harborside International Golf Center are a few top places to visit.

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.

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.

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 take a trip to 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 with a stop at 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

$27

per adult

86% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47

per adult

88% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

90% of travellers recommend

See all activities in Far Southwest Side

Far Southwest Side Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$113 nightly

$135 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,288 reviews)

"Convenient to many attractions. Comfortable room. Fastest elevators! Favorite place to stay in Chicago!"

Reviewed on Aug 23, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$125 nightly

$148 total

Aug 31 - Sep 1

Total with taxes and fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (865 reviews)

"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"

Reviewed on Aug 21, 2026

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See all 4,639 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.