Southwest Side Vacation Packages 2026 from $724

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The Latest Southwest Side vacation packages

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

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$724

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (518 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$885

per person

Oct 28 - Nov 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (4,907 reviews)

Incredible hotel — it was clean, the room was spacious, the staff were incredibly friendly, and it was conveniently located in the heart of downtown, within walking distance of everything we needed.

Reviewed on Aug 21, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,101

per person

Oct 27 - Nov 3

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (550 reviews)

Excellent front desk staff. Great place, very clean with a touch of everyday luxury. Highly recommend!

Reviewed on Aug 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$966

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)

Beautiful place to experience

Reviewed on Aug 22, 2026

The Talbott, Autograph Collection

Downtown Chicago

Save 100% on your flight

$911

per person

Oct 27 - Nov 3

found 2 days ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (157 reviews)

Front desk manager agreed to change my date with on-line service from the next weekend to the current weekend, so I booked and checked in. 4 days later, the on-line booking co. Said the manager did not agree to release my reservation. Unethical procedurers.

Reviewed on Aug 12, 2026

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Where to stay in Southwest Side

Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side

A colorful mural on a concrete wall with various figures and buildings.

Back of the Yards

2 out of top 10 points of interest in this area

While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.

Clearing

You'll appreciate the restaurants during your time in Clearing and you might want to plan a stop by Wintrust Sports Complex and SeatGeek Stadium while you're in the area.

An airplane exhibit labeled "Concourse A" in an airport terminal.

Garfield Ridge

Be sure to check out the restaurants and churches while you're strolling through Garfield Ridge, and hop on the metro at Midway Station to see more of the surrounding area.

An aerial view of a residential area with autumn-colored trees and houses.

West Lawn

2 out of top 10 points of interest in this area

Travelers enjoy West Lawn for its restaurants and museums. Consider checking out Balzekas Museum of Lithuanian Culture while you're in the area.

Brighton Park

The restaurants and shopping are a few reasons travelers visit Brighton Park. Though there aren't many top sights in the neighborhood, you can visit United Center and Bridgeport Art Center, a few notable attractions nearby.

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)

After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

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Balzekas Museum of Lithuanian Culture

10.0/10 (1 review)

You can spend time exploring the galleries in Balzekas Museum of Lithuanian Culture in Chicago. Stroll along the lakeside in this vibrant area, or check out its top-notch restaurants.

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S.S. Peter and Paul Church

After visiting S.S. Peter and Paul Church, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

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Union Stock Yard Gate

You can find out about the history of Chicago with a trip to Union Stock Yard Gate.

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Ephraim Bajar Cultural Center

Enjoy an outing to Ephraim Bajar Cultural Center during your stay in Chicago. Amble around the area's parks or visit its churches.

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What to do in 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 Southwest Side

Southwest Side Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

8/10 Very Good! (10,276 reviews)

"Very nice hotel. We had a King size bed overlooking Buckingham fountain. Booking a park view room is highly recommended. The shower/bathroom is on the smaller end, however, knowing the history of the hotel, it comes at no surprise. The hotel itself has so much history and has quite a few famous guests ..."

Reviewed on Aug 21, 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 nightly

$170 total

Aug 23 - Aug 24

Total with taxes and fees

8/10 Very Good! (2,063 reviews)

"Incredible Gold Coast location and the bar staff was great. The room however was really bad, run down, broken furniture, holes in sheets. Shocked honestly. In speaking with other guests on elevator/ my experience was similar to theirs. Really unfortunate. I let staff know - zero follow up or care. ..."

Reviewed on Aug 21, 2026

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (863 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 4,920 properties in 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.