Southwest Side Vacations from $237
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$311
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,404 reviews)
Great views, terrible service. Unfortunately I did not enjoy my stay because of the overwhelming rudeness of the staff. The front desk looked around as I approached, both arriving and checking out. Fully staffed but I had to alert them I was standing there. The bell hops were excellent. Very friendly. As well as the bartender in the lobby and the waitress on the rooftop. However everyone else not so much. Please work with your frit dosk staffers. As they set the tone.
Reviewed on Oct 8, 2026
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See all available trips from Columbus to Southwest Side
View all tripsWhere to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
Englewood
1 out of top 10 points of interest in this area
While you're strolling through Englewood, you may want to check out the beaches and restaurants. If you want to see more of the area, hop on the metro at Halsted Station or 63rd Station.
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.
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.
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.
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 Plaza Garibaldi and United 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.
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.
Union Stock Yard Gate
You can find out about the history of Chicago with a trip to Union Stock Yard Gate.
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 fascinating museums.
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.
What to do in Southwest Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
$158
per adult
80% of travellers recommend
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$122 nightly
$144 total
Nov 5 - Nov 6
Total with taxes and fees
8/10 Very Good! (10,230 reviews)
"Incredibly dated property. Only one of the two elevators worked. TV in the room was at least 15 years old and the whole picture didn’t fit on the screen. AC was not able to be control effectively."
Reviewed on Oct 8, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$152 nightly
$181 total
Oct 25 - Oct 26
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
$170 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Southwest Side Vacation Packages
Southwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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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.
