Southwest Side Vacations from $262
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The Latest Southwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Crown Point
Save 100% on your flight
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (530 reviews)
I liked how quiet it was and how nice and friendly the staff was. The room was a little dusty but it wasnt overwhelming.
Reviewed on Jul 29, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,253 reviews)
The location of the hotel right off Michigan Avenue was perfect. Public parking right across the street. The hotel is fresh and new. Many staff available to assist. Do not skip the complimentary breakfast! I would easy pay $20 for that breakfast as it had everything from fresh fruit, real eggs, pastries, even a coffee cream warmer/frother machine for the great coffee!
Reviewed on Aug 6, 2025
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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
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.
Discover the most popular places to visit in Southwest Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side
Chicago Sightseeing River and Lake Cruise
$45
per adult
100% of travellers recommend
Southwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $184 total per night from Sep 1 to Sep 2
$184 total
Sep 1 - Sep 2
Total includes taxes and fees
7.8/10 Good! (8,956 reviews)
"We stayed in a family suite. Both rooms were large. The beds were comfortable."
Reviewed on Aug 4, 2025
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $229 total per night from Aug 22 to Aug 23
$229 total
Aug 22 - Aug 23
Total includes taxes and fees
8.2/10 Very Good! (1,830 reviews)
"Love the gym!"
Reviewed on Aug 5, 2025
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Fully refundable
$146 nightly
The price is $171 total per night from Aug 24 to Aug 25
$171 total
Aug 24 - Aug 25
Total includes taxes and fees
8.8/10 Excellent! (1,351 reviews)
"I liked the in and out parking access for one rate per day."
Reviewed on Aug 6, 2025
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.
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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.